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The consensus is that if you get booed, you want to go home immediately and just go cry in a corner.
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But to me, I was one of the first comedians up and I failed.
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I failed horribly.
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I go, all right, well, let s see what they laugh at.
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Let s figure out what is it that I didn t do that I can do better next time.
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Hey, welcome to the Art of Charm.
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I m Jordan Harbinger.
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I m here with producer Jason DeFilippo.
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What s up?
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Today we re talking with my friend Roy Wood Jr.
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He s a correspondent on The Daily Show with Trevor Noah.
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He was also on a sitcom called Sullivan and Son with my BFF and fellow AOC show guest Caleb Bacon.
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Variety called Roy Wood Jr.
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one of the 10 comics to watch.
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I would agree with that.
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Today we re gonna talk about how getting arrested jump-started his career path.
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hacking his path in comedy, using some social engineering skills, and a concept he calls skipping a level in the role this has played in his career.
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We ll also talk about life on the road, the grind, and staying visible and relevant in a hyper-competitive landscape.
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We re glad to have you with us here today at AOC, so enjoy this episode with Roy Wood Jr.
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Oh, and by the way, if you re new to the show, we d love to send you some top episodes and the AOC toolbox.
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This is where we discuss things like reading body language and having charismatic nonverbal communication, the science of attraction, negotiation techniques, social engineering, network and influence strategies, mentorship, persuasion tactics, and frankly everything else that we teach here at the Art of Charm.
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Check that out at theartofcharm.com slash toolbox, and at theartofcharm.com slash podcast, that s where you ll find the full show notes for this and all previous episodes of the show.
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Alright, here s Roy Wood Jr.
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You got an early start in college, from what I know, doing the comedy thing, Roy.
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It seems like you had a rocky start, a hesitant start, and an early start.
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Yeah, it was weird for me.
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So I started stand-up when I was 19.
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And so I was in school and me and a couple buddies thought it d be cool to steal some jeans from Dillard s.
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Shout out to Dillard s department stores.
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And the Tallahassee Police Department disagreed with this decision.
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And so in the midst of all of that, you get arrested and they charge you with stealing jeans and theft, and you gotta do probation and all of that.
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But before I got sentenced, I thought I was going to prison for life.
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Because at the time, you gotta remember, my 19-year-old brain, my only image of jail is the television show Oz.
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Now, Oz at the time on HBO,
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this show is averaging four rape scenes an episode on average on a good week maybe like two but on a really bad like say a midseason finale oh it s gonna be eight stabbings and six rapes so I figured that was the life that awaited me for stealing two pairs of Levi jeans so
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The deal I made with myself was before I go to prison, I m going to do everything I ve ever wanted to do in life.
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And comedy was on the list.
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It s really just that simple.
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It was something I always wanted to try, but never had the guts to do when I was in high school, because I bounced around from school district to school district most of my childhood.
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I was really never anywhere.
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It wasn t until high school
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that I was at a school for more than two years.
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So we were still in Birmingham.
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I was in like these gifted programs and my mom was always trying to find which school has the best teachers this year.
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I don t know if my mom had like some weird fantasy school teacher roster or she always knew where the best
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teachers and the best programs were.
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So as schools lost programs and other schools acquired them, it was a constant game of leapfrog.
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So it s hard to become a steady member of the social scene during that time.
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So I had a hard time fitting in until high school.
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So I didn t want to try comedy.
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But then when you re faced with being stabbed and raped eventually in federal prison or something like it was, as the thought was in my head,
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comedy becomes a lot less daunting of a task.
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So I gave it a shot and that was December of 98 and I ve been doing it ever since.
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And, you know, that was one of those moments for me where it s like, all right, you ve hit a rocky patch.
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You got to figure it out.
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And that was definitely the catalyst.
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I honestly feel like if that doesn t happen, I probably never get the courage to attempt stand up comedy, because why?
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You get a degree and you live comfortably, but
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I would have never known or tried to ascertain my potential because the mistake had never been made.
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The rock bottom moment had never happened.
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So for me, it was wonderful that it happened.
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I ve said this on TV before, that was the best thing that ever happened to me.
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To get arrested for shoplifting?
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Getting arrested, hands down, was the best thing that ever happened to me.
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because it was an ultimate pivot point in my life.
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It didn t take two days for me to realize what the hell I wanted to do.
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I had a plan laid out of how I wanted to go about doing it.
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And three years later, I had a college degree and a decent career.
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In a lot of ways, I got very lucky, man, because I went to a school, Florida A&M, that cared enough about me as a student
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to not expel me because a lot of these colleges, a lot of black colleges, and I don t, I can t speak for predominantly white institutions, but a lot of black colleges hold kids to a standard of ethics.
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So if you re a student here, you will behave yourself.
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You will not act like an ass all over town, because that s still a reflection on the legacy of the school.
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So they would have been well within their rights to expel me if they wanted to.
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They saw fit not to, and there were enough people who believed that there was still a decent human being deep down inside of me.
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So
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I got to stay in school.
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And with that, it gave me the structure I needed to do comedy in the early days without there being a lot of fiscal risk, because comedy is a career path.
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I d say the first five years, the curve might be a little shorter now because there s more TV opportunities, but in 98, you re looking at a five to 10 year run.
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I d say five years before you can pay your bills realistically, 10 before you can really be supporting yourself.
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So for me, being in school lowered the stakes.
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I had two roommates.
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I had a part-time job at Golden Corral.
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That covered the bills.
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So when I got back in school, I consolidated all of my classes to three days a week, Tuesday, Wednesday, Thursdays.
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I used Thursday night to take the Greyhound.
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Friday, Saturday, Sunday, do shows.
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Sunday night, back on the bus.
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Back in Tallahassee, mid-morning on Monday, would work a shift at Golden Corral.
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Monday night, pop up Tuesday morning, wash, rinse, repeat.
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How many years did you do that?
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It was about two years.
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So for me, it was a really good learning ground, but it was low stakes.
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So when I graduated, here s the curveball though.
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So I graduate from college with a degree in broadcast, but because all I did was stand-up comedy in my free time,
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I have no internships.
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I have no experience.
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So I have a degree in a field that basically demands that you already have some level of experience.
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And I did the math and I was making $12,500 a year doing comedy at that point.
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The first year I did stand up, I think I made like $6,000 total.
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Did it pay for the bus?
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Paid for the bus, right?
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Pretty much.
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Yeah.
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I mean, that pretty much was all it paid for.
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The second year was a little bit easier because my grades got better my junior year of college.
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My mom,
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put a down payment on a car for me, a 2001 Ford Focus.
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So I had a car.
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So the car made getting to gigs a lot easier.
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It also meant that I could go further to go get work.
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So because of that, I went from about $6,000 a year to $12,000.
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So when I graduated, I graduated in April, and I remember this because it was around the same time I was doing my taxes.
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And I had two job offers
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where journalism was concerned.
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And they were both at newspapers and one was going to pay me $10,000 for the year and the other one was going to pay $14,500.
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And so I went to my mom and I said, look, I know you re not crazy about me doing comedy, but it s competitive in terms of
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salary.
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So the deal I made with my mom was, you give me three years max to live with you after graduation.
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For as long as I make more money than I did the year before, I get another year in your house.
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Up to three years.
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And so after two years, I moved out.
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Nice.
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And that was the beginnings of it.
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I mean, you know, people go, well, when did you go full time?
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When did you let go of your job?
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And when did you take that plunge?
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To me, I ve always been full time.
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I ve never said yes to something in the place of comedy.
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Comedy takes
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supersedes everything.
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Like, I love what I do, and I always have, and it worked out perfectly that I was able to schedule a college education for two years around it, but I wonder what would have happened if I wouldn t have been able to, because that gave me life.
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I felt alive from the moment I was on stage.
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Nothing else mattered.
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It was therapeutic.
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It still is.
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It s escapism.
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It s as much for me as it is to people who pay to see me.
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Good point.
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If we re going to be honest.
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Yeah.
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So, you know, if we re talking about my beginnings, that s a pretty good summation of the rocky start.
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And then that just rolled into a guy willing to drive anywhere.
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to perform for anybody.
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If you have a stage and a microphone, I m there.
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I ll sleep in my car, I ll figure out the rest of it on the back end.
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So for me, it was fun.
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I look back on those years with a lot of reverence, because that was my college.
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Yeah, your education.
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Yeah.
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And I don t know if these guys know that they re doing it,
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But you re kind of getting mentored by the older comics, because you re 20, you re 22 years old, and you re opening for these 45 and 50 year old men, and you re watching how they carry themselves, some good, some very horribly, and you start, without knowing it, logging all of that behavior away.
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And so now, to be where I am now, almost 20 years in,
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I definitely have a scope of kind of what to do, what not to do, how to approach certain situations and bookers and business dealings because I ve been through a lot on the professional side.
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So that s a good thing.
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I think a lot of folks accidentally find out what they wanna do by failing at something else.
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It s just usually not crime that they fail at to find out what they wanna do.
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What was it like the first few times on stage when you were like, alright, I m gonna do comedy, otherwise I m gonna go to federal, you know, butt-rape prison?
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I m gonna go to Oz.
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Right, you re going to Oz.
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Were you, at that point, freaking out, or were you like, I might as well enjoy this, because I might be locked out for a minute?
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Yeah, scared of what?
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In two months, you re going to get murdered in jail.
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That was the only thought in my head is that this is how I m going to go out.
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I m going to get murdered in prison.
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So I m going to do comedy.
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Scared of what?
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A bunch of strangers?
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So that was the other thing.
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I went out of town to do open mics.
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I didn t do open mics in Tallahassee.
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Tallahassee is too small socially.
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I didn t want to get booed and then see these people.
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in the streets somewhere.
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So I would take the bus to Atlanta, I would perform at Uptown Comedy Corner, back when it was still in Buckhead.
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I would go over to the Comedy Club Stardome in Birmingham, and I would do open mics there, and I would just do weird hole-in-the-wall places in South Georgia until I got it together.
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But
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you know those first few times on stage were pretty cool because of course there s nervousness but I was prepared and you know before I ran my first open mic set you know I d already studied stand-up and had been a student of it and it was a guilty pleasure to watch BET s comic view every night and analyze all the guys and
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this joke and I would try to predict which way punch lines would go because I was trying to see how these guys were thinking and more often than not if I guess where you were going and you didn t go that place then to some degree I ve kind of figured out a joke for myself or I have this
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germination of a thought on a similar topic.
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So creatively, it was helpful.
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I wrote out my act.
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I ended up taping over it.
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It doesn t exist anymore unless the comedy club has a copy of it.
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But it was definitely well-rehearsed.
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I was up in my room, running the set over and over and over and over again.
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And it was fine.
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I got booed one night in Atlanta.
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And I still stayed and watched the show.
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And I remember hearing one of the waitresses go, he stayed.
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Like, it just made me laugh.
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Because the consensus is that if you get booed, you want to go home immediately and just go cry in a corner.
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But to me, I was one of the first comedians up and I failed.
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I failed horribly.
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I go, all right, well, let s see what they laugh at.
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Let s figure out what is it that I didn t do that I can do better next time.
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So as far as I was concerned, I got booed.
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That s cool.
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I don t know y all.
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I m not going to see you again.
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So I m going to sit right here with my two drink minimum and analyze every comedian that comes on stage after me.
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and figure out what they re doing and take note, so that the next time I come, maybe I ll do a little bit better.
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The other alternative there would have just been, I m gonna go to my crappy-ass hotel room and just cry about how these strangers didn t like my jokes, and you re not gonna give up comedy, so you might as well stay and learn.
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And also, man, I ve definitely seen bad comics.
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I m not walking up to them after the show on the way to the bathroom and being like, you sucked!
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Like, nobody s doing that.
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Right?
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It s very awkward when you fail and people know you failed and then you have a moment with those people.
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Like, it s just, it s very awkward.
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I m also flattered that you think that I had a hotel room when I was doing Overmatch.
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I would take the MARTA back to downtown Atlanta and then get off at the Greyhound station stop and sit in a chair for four hours and wonder what the hell I m doing with my life.
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And just read magazines.
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Oh man, and this is before smartphones, internet, so you literally were just like, let me find something laying on the floor or like in a garbage can that s not dirty.
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Did you bring reading materials?
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Because I couldn t afford a laptop, so I didn t have a laptop, but you know, there was always something decent to read.
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I was pretty deep off into papers and weird magazines and stuff, so you know, I d read a lot of that.
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It s very, very interesting how you can look back on those times and see the moments where you learned something and see... Because, you know, most guys, even now, I see comics who leave open mic and I m like, where you headed?
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Oh, I m headed home.
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And I m just like, all right.
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I mean, more power to you, but for me, I learn as much by watching as I do performing.
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So for me, it s important for me to watch as much comedy and absorb as much stand-up comedy as I possibly can, even now.
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At AOC, we teach a lot of analyzing human behavior, other people and our own, especially our own, I should say, to develop self-awareness.
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When you re looking at comics to learn from them, what are you looking for?
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Are you listening for comedic timing?
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Are you just looking at the material and their jokes?
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I mean, I guess I don t know that much about comedy to even be able to disassemble an act.
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You don t know until you see it.
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You don t really know what you re looking for until you go, oh, I see what he did there to make that better.
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You take a guy like, say, Jim Gaffigan.
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Jim Gaffigan is a great minimalist in terms of vocal inflection.
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He s not yelling, he s not, it s just one monotone voice, and it s, did you ever notice, wow, hmm, yeah.
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SPEAKER_01
Which, when Gaffigan does go up in tone, or he drops down into the whisper that he does sometimes, it makes it more pronounced, the change is more pronounced, because there aren t a lot of vocal variations leading up to the change, if that makes sense.
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He s a good guy to look at for intonation, because if there s a joke that the delivery can be funnier than the punchline, or you have a joke where the punchline is funny but the delivery is off, you can enhance a joke by doing things.
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And just because you see someone else do it doesn t mean that you can do it, but it s ways that you can make yourself better.
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I ve learned that for myself, moving only on the punchline enhances the punchline.
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If it s an explosive punchline, then I need an explosive movement, a quick arm flail, a quick half step forward, or a jab step backwards.
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Like, something as slight as changing your physical position on stage can enhance or take away a joke.
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Or if you re doing an impersonation of someone, I ve learned that, you know, like, generally if comedians are doing something where two people are talking, where like,
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You turn to the left to represent one voice and then you turn back to the right to represent the other voice to create the illusion of two people facing each other to create a conversation.
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SPEAKER_01
Well, in that half second turn of you doing both voices, for me, it looks awkward.
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SPEAKER_01
It feels awkward.
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It s half a second of silence that I can t feel.
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It s easier for me to literally look down at the floor for one voice and look up at the audience for the other voice.
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And just that small execution for me is something that helps.
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And you don t pick up on that until you see someone that s doing something you wouldn t do.
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You go, well, I wouldn t do it like that because that doesn t work for me.
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SPEAKER_01
Well, how would I do it?
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SPEAKER_01
Oh, I would do it this way.
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And then you change it out.
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SPEAKER_01
Chris Rock is a great stage stalker.
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SPEAKER_01
What does that mean?
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SPEAKER_01
You know, he stalks, he pranks.
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Francis back and forth.
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He s like a caged tiger, where he s back and forth across the stage the entire time, constant motion like a shark, which makes his material seem more precise and thought out.
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SPEAKER_00
It helps it, because there s a confidence to just walking back and forth and talking while you walk, and there s an assuredness in that.
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SPEAKER_00
yeah like some swag george carlin barely moved and richard pryor might drift to one side of the stage or the other but there s so many different ways to do comedy and so you start watching and seeing what other comedians are doing you know it could be something as simple as
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where you put the mic stand while you re on stage.
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SPEAKER_00
Do you hold the mic stand like a gear shift?
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Do you lean on it like a pole?
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Leaning on it is a deflated energy.
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SPEAKER_00
So if you re doing a high energy joke while leaning, that doesn t work.
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I used to have a horrible habit on very shallow stages if the wall was within reach.
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I used to have a really bad habit of leaning up against the wall or putting my hand on the wall.
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And so now I put the mic stand between myself and the wall so that if I go to lean, I have to step around the mic stand.
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SPEAKER_00
I m basically creating a fence for myself.
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SPEAKER_00
And I had to do that for a long time to keep from doing that because leaning deflated my jokes because my jokes have a higher energy to them.
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SPEAKER_01
Yeah, I can see that you use your own psychology against you to learn a lot of this stuff.
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SPEAKER_01
I mean, first of all, I know you didn t really come up with other comics, right?
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SPEAKER_01
Like a lot of people in Hollywood and stuff, they re like, oh yeah, we came up together, Laugh Factory, da-da-da.
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SPEAKER_01
You were in Alabama and touring around Georgia.
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SPEAKER_00
Yeah, kind of a nomad.
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SPEAKER_00
Yeah, pretty much the comedy scene in the south is very diverse And it s a lot of people at different stages of the game and generally speaking Unless you cross paths at an open mic You re not working with the same guys every week once you start featuring and becoming an opening comic on comedy shows around the south you don t know who you re getting paired with this week and
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SPEAKER_00
you ll see the same faces over the course of a year but every year you re not working with the same guys at the same level and you know that sense of camaraderie that you see from comics from the coast I don t think many southern acts have that.
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SPEAKER_00
It s starting to become that way in Atlanta and maybe Nashville now where there s guys that we all started together and they have a round of rooms that they all did repeatedly but
2
SPEAKER_00
98, 99, if you want to get on stage every week, you got to drive four hours.
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SPEAKER_00
Yeah.
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SPEAKER_00
It was none of this being in the same city all month.
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SPEAKER_00
I didn t have that luxury.
2
SPEAKER_00
I wish I did, but I didn t.
2
SPEAKER_00
You know, there s some guys from the Houston scene and Texas.
2
SPEAKER_00
There s a lot of overlap and there s probably some camaraderie, but coming out of Alabama, no.
2
SPEAKER_00
You know, there s guys I know to say we had the same relationship is like when you hear George Wallace talk about how him and Seinfeld would
2
SPEAKER_00
We do shows and then we go up to 53rd Street and split a slice of pizza.
2
SPEAKER_00
I don t have any of that.
2
SPEAKER_00
There s a lot of guys I work with, but it s not in that same camaraderie.
2
SPEAKER_01
Right, you re not like, I got evicted this month, can I sleep on your floor?
2
SPEAKER_01
And then the next month he gets evicted and he s sleeping on your floor.
2
SPEAKER_01
You hear those stories a lot among comedians.
2
SPEAKER_01
What kept you going at this point though?
2
SPEAKER_01
Did you track or chart your progress in some way?
2
SPEAKER_01
How do you even know you re moving forward in that business?
2
SPEAKER_00
The goal every year with comedy, and it s still now, it s the same thing, the goal is to do better than the year before.
2
SPEAKER_00
How do you measure doing better than the year before?
2
SPEAKER_00
Well, for me, I measured it by
2
SPEAKER_00
new rooms acquired or increase in money in rooms that I ve already started working.
2
SPEAKER_00
So are you getting paid more or are you working new places?
2
SPEAKER_00
And you need to be answering yes to one of those questions every single year.
2
SPEAKER_00
That was it.
2
SPEAKER_00
The goal when I started, shit man, when I first started, my goal every month was to perform in one new city.
2
SPEAKER_00
That was a base level, simple, attainable goal, was once a month, find a new city to tell a joke in.
2
SPEAKER_00
And that was very easy in Florida.
2
SPEAKER_00
Florida,
2
SPEAKER_00
I would argue, I don t have the stats on it now, but I would argue per capita, not even per capita, just period.
2
SPEAKER_00
Florida probably has more comedy clubs or more comedy nights than any state in the country because you have all of the main week-long clubs and then you have these weekend rooms, but then you also have a shit ton of just one-nighters and just hole-in-the-wall comedy dumps in the middle of nowhere
2
SPEAKER_00
that in those days there was way more work in Florida.
2
SPEAKER_00
Like I would argue that Florida has more comedy clubs than California or New York.
2
SPEAKER_00
Now you gotta drive eight hours total.
2
SPEAKER_00
I m just saying as a state.
2
SPEAKER_00
You could do Orlando, you could do Altamont Springs, and then you could do Kissimmee, and that s all within 30 minutes of each other.
2
SPEAKER_00
So there was a lot of places to go.
2
SPEAKER_00
And then Georgia had a ton of rooms, so
2
SPEAKER_00
It s just go somewhere different.
2
SPEAKER_00
The growth is on the horizon.
2
SPEAKER_00
So for me, it was go somewhere different.
2
SPEAKER_00
Then once you start saturating yourself in most of the markets, like let s say from Wichita, Kansas, all the way down to Jacksonville, Florida, like just that whole Southern Midwest Cleveland on down, you know, I-75 or whatever.
2
SPEAKER_01
Yeah, I-75 from Detroit all the way down to the Keys.
2
SPEAKER_01
Correct.
2
SPEAKER_00
So that whole 75 corridor and that whole I-70 east-west from Virginia Beach to Kansas City type area, you know, I was doing pretty good because you starred as an emcee.
2
SPEAKER_00
You keep doing well as an emcee.
2
SPEAKER_00
They promote you to a feature act.
2
SPEAKER_00
You do well enough as a feature act.
2
SPEAKER_00
you get promoted to a headliner.
2
SPEAKER_00
I had cities on my calendar every year that I was at a different point in the road comic life cycle.
2
SPEAKER_00
Some rooms were featuring me, while some rooms were emceeing me.
2
SPEAKER_00
And some rooms weren t emceeing me, but they were giving me guest sets.
2
SPEAKER_00
So I could go to a room and do a guest set, and then send that tape to a room that I wanted to work to get in with a comedy club, right?
2
SPEAKER_00
You either need a recommendation,
2
SPEAKER_00
or you need to perform on the open mic and do well or you need to send in an audition tape and if the booker watches the tape and likes it then he ll book you to come and you know hey you can come emcee i saw your tape it s basically sending your resume you re basically applying for a job in every city and i was set up my two vcrs
2
SPEAKER_00
run my AV cords and make my audition tapes and mail them out and every four weeks I would do a follow-up email on the audition tape and two weeks after that I would send a fax with my avails and if I didn t get a reply from any of these clubs then about two months after I sent the first tape I would send a new audition tape
2
SPEAKER_00
to that same club with the letter, hey, I ve had a chance to do some other stuff.
2
SPEAKER_00
I know you get bogged down with a lot of videos, but I just want to make sure you have my most up-to-date stuff if ever you get around to watching it.
2
SPEAKER_00
Nine times out of 10, it was the same fucking jokes I sent you two months ago.
2
SPEAKER_00
But you don t know, because you didn t watch the tape.
2
SPEAKER_00
Because if you d watched the tape, you d have told me yes or no.
2
SPEAKER_00
And I know you would have told me yes or no, because I ve been emailing and faxing.
2
SPEAKER_00
For me, I was just never going to be ignored.
2
SPEAKER_00
I didn t care about no.
2
SPEAKER_00
No was welcome.
2
SPEAKER_00
It means you responded.
2
SPEAKER_00
It means you see me.
2
SPEAKER_00
It means you observed me.
2
SPEAKER_00
So what I would do, what I figured out with certain rooms, certain rooms only respect you if you work other rooms.
2
SPEAKER_00
I had a really big advantage because I was from Birmingham, and the comedy club in Birmingham, the Stardome to this day, is still one of the most respected rooms in the country.
2
SPEAKER_00
So having that club on my resume opened up Memphis, Nashville, Knoxville, Chattanooga, some parts of Kentucky.
2
SPEAKER_00
So I was trying to get in with the comedy club in Dayton, and what I discovered is that in some markets, if you could look like you were already working somewhere,
2
SPEAKER_00
they would book you on the strength of you already working somewhere.
2
SPEAKER_00
So a club like, say, there was a club in Dayton at the time called Jokers, and I m not sure if this was where I did this trick.
2
SPEAKER_00
I did it a bunch of times to a lot of rooms, but
2
SPEAKER_00
Let s just use that for an example Dayton was a major club, but a smaller city the goal was to get a guest set in Cincinnati or Columbus Ohio which were more respected rooms than Dayton but also in the same region if you follow me mm-hmm sure because clubs have regional relationships if you work for this guy then you can work for me and all of that shit and
2
SPEAKER_00
I m not in with Cincinnati or Columbus, but the goal is to get in with Dayton.
2
SPEAKER_00
So I contact Cincy.
2
SPEAKER_00
I emailed the club owner in Cincy and the club owner in Columbus.
2
SPEAKER_00
And I go, hey, I m a comic.
2
SPEAKER_00
I m passing through.
2
SPEAKER_00
I m headed to do a gig in Detroit.
3
SPEAKER_02
or I m headed to do a college in Erie.
3
SPEAKER_02
Like, it was always a gig that you couldn t quite verify.
3
SPEAKER_01
Right, right, sure.
3
SPEAKER_01
Just not enough detail for them to call and check it out.
3
SPEAKER_02
Yeah, but hey, I ve already performed in these cities south of you, but I m headed to the city north of you.
3
SPEAKER_02
I have a night off.
3
SPEAKER_02
Would love to work on a tight six-minute set that I m submitting for showcases.
3
SPEAKER_02
You basically contact this booker.
3
SPEAKER_02
You ve already said two things.
3
SPEAKER_02
One, I m a working comic.
3
SPEAKER_02
Two, I m headed somewhere to work and do stuff.
3
SPEAKER_02
And three, I m submitting for a showcase.
3
SPEAKER_02
You don t know for what.
3
SPEAKER_02
What showcase?
3
SPEAKER_02
And you can t Google showcases, because more often than not, they re not public knowledge.
3
SPEAKER_01
Well, given the fact that you were freaking faxing people and mailing VHS tapes to them, they re not Googling anything anyways.
3
SPEAKER_01
This is like- Exactly!
3
SPEAKER_02
This is the beginning of DVDs and DVD burning.
3
SPEAKER_02
And at that time, it still cost money to have a DVD burner.
3
SPEAKER_02
So guys weren t just mailing out DVDs yet.
3
SPEAKER_02
So eight times out of 10, it worked.
3
SPEAKER_02
And I could get a guest set at a club.
3
SPEAKER_02
I wasn t passed that to MC.
3
SPEAKER_02
So I would come in and do the guest set, record the guest set.
3
SPEAKER_02
I would go home and edit the guest set to chop off the intro and the outro.
3
SPEAKER_02
So let s say I did a seven minute set.
3
SPEAKER_02
I would cut off me saying hello and cut off me saying goodnight.
3
SPEAKER_02
Take that snippet, mail that to Dayton and tell them that I just worked Cincinnati.
3
SPEAKER_02
Which isn t a lie.
3
SPEAKER_02
Technically, I did work Cincinnati.
3
SPEAKER_02
You don t know that that was a guest set.
3
SPEAKER_02
You think that you re watching a snippet of a longer set.
3
SPEAKER_02
Right.
3
SPEAKER_02
And so that sometimes was enough to get me in with a lot of clubs.
3
SPEAKER_02
Hey, you should work me.
3
SPEAKER_02
I work Cincinnati.
3
SPEAKER_02
Oh, well, I had a fallout this week.
3
SPEAKER_02
If you want to emcee or do you want to come and feature for one night?
3
SPEAKER_02
Hell yeah, I do.
3
SPEAKER_02
Nice.
3
SPEAKER_02
I have no bills because I live with my mom.
3
SPEAKER_02
So far.
3
SPEAKER_02
I had to pay my car note, car insurance.
3
SPEAKER_02
I think I was paying my health insurance at the time.
3
SPEAKER_02
Like it was, all I needed to cover was like 400 bucks a month, maybe five when I was living with my mom.
3
SPEAKER_02
And at this point I just started doing morning radio back home, but they gave me freedom of travel.
3
SPEAKER_02
I was selling prank call CDs after shows.
3
SPEAKER_02
Like there was a lot of ways to scrap together a little bit of money.
3
SPEAKER_02
So when you say measure growth,
3
SPEAKER_02
Am I working somewhere new or am I getting paid more for where I m working?
3
SPEAKER_02
And then that graduated to am I getting television opportunities?
3
SPEAKER_02
Am I getting opportunities to skip a level?
3
SPEAKER_02
Like I feel like entertainers, you get two to three opportunities a year, no matter where you are in your career.
3
SPEAKER_02
You get two, maybe three opportunities a year to skip a level.
3
SPEAKER_02
You get a chance to do something that really moves the needle and really opens another door of opportunity for you.
3
SPEAKER_01
are funny, like I didn t know, of course, about the social engineering and the hacking of getting into clubs, but I did dig up a little something.
3
SPEAKER_01
I know you were a radio guy for like 11 years in Alabama, which is where I assume you crafted this sort of artful sense of frustration that comes through in your comedy sets, but you also hacked a comedy show to get the radio job in the first place.
3
SPEAKER_01
Tell us that story.
3
SPEAKER_02
Oh, dude, that s what you have to do.
3
SPEAKER_02
Everybody s lying, dude.
3
SPEAKER_02
It s only lying if you can t back it up, man.
3
SPEAKER_02
Like everything else is just, I don t want to say manipulation because that suggests a negative.
3
SPEAKER_02
We call it social engineering.
3
SPEAKER_02
You kind of hacked this one, right?
3
SPEAKER_02
I mean, this was like, it s a hack.
3
SPEAKER_02
So I was having trouble at the comedy club in Birmingham of moving up.
3
SPEAKER_02
I was doing open mics.
3
SPEAKER_02
The progression generally is you do open mics for X amount of months.
3
SPEAKER_02
You do well enough on open mics, they add you to the rotation of MCs on the main shows that happen in the main showroom.
3
SPEAKER_02
That s where you want to be.
3
SPEAKER_02
That s where the shine is.
3
SPEAKER_02
That s where the real audiences are.
3
SPEAKER_02
It s basically JV to Varsity.
3
SPEAKER_02
I m having trouble getting bumped up to Varsity in Birmingham.
3
SPEAKER_02
At the same time, when I moved home, this is April of 2001,
3
SPEAKER_02
The local radio station was having a contest for who s funny in Birmingham.
3
SPEAKER_02
Basically, they were trying to replace Ricky Smiley on the radio in Birmingham.
3
SPEAKER_02
And so Ricky was and still is comedy god in Birmingham, Alabama.
3
SPEAKER_02
You know, he s got the syndicated stuff now, so he s doing big things.
3
SPEAKER_02
In those days, Ricky Smiley was irreplaceable.
3
SPEAKER_02
And so every comedian up until that point, the radio station didn t really vibe with, they didn t like them.
3
SPEAKER_02
So they canceled the contest.
3
SPEAKER_02
They didn t even choose a winner.
3
SPEAKER_02
They were just like, nah, we re just not going to have a comedian.
3
SPEAKER_02
We ll just be a morning show without a comedian before we have one that s not funny.
3
SPEAKER_02
So here I am at this point, two years in the comedy.
3
SPEAKER_02
with a degree in journalism and experience in radio.
3
SPEAKER_02
So I go to the guy who s hosting the show, his name is Buck Wilde, and I say, Buck, I m a new comedian in town, I d love an audition.
3
SPEAKER_02
And he goes, nah, you can t do it, we already canceled the contest, thank you a lot, maybe later on or something like that.
3
SPEAKER_02
I go, all right, man, fine.
3
SPEAKER_02
The thing I always knew about 95.7 Jams
3
SPEAKER_02
To this day, they sponsor most of the Black comedy shows that happen at the Stardome Comedy Club.
3
SPEAKER_02
And the DJs from the station go out and host
3
SPEAKER_02
the night, like they go out first before the first comedian.
3
SPEAKER_02
Hey, everybody, make sure you listen to our radio station.
3
SPEAKER_02
Who won a T-shirt?
3
SPEAKER_02
Thank you.
3
SPEAKER_02
And then they walk off stage and then the first comedian comes out.
3
SPEAKER_02
So I go to Bruce Ayers at the Stardome at the Comedy Club.
3
SPEAKER_02
I go, yo, man, I just started at 95.7 this week.
3
SPEAKER_02
I m the new comedian on the morning show.
3
SPEAKER_02
Instead of Buck and Africa going out and hosting, they said it d be cool if I go out and do a couple minutes instead.
3
SPEAKER_02
And I could just say what s up, do a couple jokes, and pop off the stage.
3
SPEAKER_02
And Bruce goes, oh, well, congratulations.
3
SPEAKER_02
Way to go.
3
SPEAKER_02
That s really good.
3
SPEAKER_02
That s really good of you.
3
SPEAKER_02
See you Friday night at 730.
3
SPEAKER_02
I go, yes, sir.
3
SPEAKER_02
So then I go back to the radio station.
3
SPEAKER_02
Mind you, I m like stalking Buckwild.
3
SPEAKER_02
I m like waiting outside the station at 10.05, waiting for him to come out the side door to the parking lot.
3
SPEAKER_02
And I go, yo man, just so you know, I ll be hosting the D.L.
3
SPEAKER_02
Hughley show this Friday night.
3
SPEAKER_02
Come early.
3
SPEAKER_02
If you like my jokes, will you put me on the air with you Monday morning?
3
SPEAKER_02
He goes, you re opening for D.L.
3
SPEAKER_02
Hughley.
3
SPEAKER_02
I go, yeah, I m opening for D.L.
3
SPEAKER_02
Hughley, which is huge.
3
SPEAKER_02
This is D.L.
3
SPEAKER_02
fresh off.
3
SPEAKER_02
Even now, it s still a big deal.
3
SPEAKER_02
But to be a local guy opening for a big national act,
3
SPEAKER_02
That raised his eyebrow.
3
SPEAKER_02
He goes, so if you re good enough to open for D.O.
3
SPEAKER_02
Hughley, hmm, okay.
3
SPEAKER_02
Well, I tell you what, if I like what I see, then maybe.
3
SPEAKER_02
I go, cool.
3
SPEAKER_02
So now all I have to do on Friday night is keep Buckwild and the comedy club owner from talking to each other and realizing that I played him.
3
SPEAKER_01
It s like when you re dating two girls at once in college, which was the only time I did this, and you re like, you just gotta get out of here, go out the back door.
3
SPEAKER_01
Right.
3
SPEAKER_02
100% bro.
3
SPEAKER_02
So show night, Bruce Ayers comes down and I m dressed to the tens.
3
SPEAKER_02
I got on my little suit and everything.
3
SPEAKER_02
Buckwild comes down.
3
SPEAKER_02
says hello and Bruce comes down and he goes okay well let s go ahead and start the show and Buck if you want to go out for two or three minutes that s fine say hello and then just bring out Roy.
3
SPEAKER_02
Roy you do five minutes I say yes sir and so
3
SPEAKER_02
Buck goes out, does the usual radio Easter speech, and it s fine.
3
SPEAKER_02
Brings me out.
3
SPEAKER_02
I have the best five-minute set.
3
SPEAKER_02
I can t even put into words how it couldn t have gone better.
3
SPEAKER_02
It was flawless.
3
SPEAKER_02
It was exactly what I needed.
3
SPEAKER_02
And as I m coming off stage, Buck Wilde is standing there, and he says, see you Monday morning.
3
SPEAKER_02
Dang.
3
SPEAKER_02
That was the beginning of my career in radio.
3
SPEAKER_02
I go back in the green room.
3
SPEAKER_02
D.L.
3
SPEAKER_02
Hughley is back there.
3
SPEAKER_02
And he goes, you did your thing, brother.
3
SPEAKER_02
Tell you what, why don t you stay on all weekend?
3
SPEAKER_02
And I got to open for D.O.
3
SPEAKER_02
Hughley for the entire weekend.
3
SPEAKER_02
And that was also how I got promoted to varsity at the comedy club, because
3
SPEAKER_02
Now you can t deny me.
3
SPEAKER_02
I just opened for DL.
3
SPEAKER_02
So of course, if I can open on your $30 special event ticket night, then hell yeah, I can emcee your $10 Tuesday night comedy show.
3
SPEAKER_02
So there was no more questioning whether I could do the job.
3
SPEAKER_02
So I essentially got two jobs from one comedy set.
3
SPEAKER_00
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SPEAKER_02
You built the skill set to really knock it out of the park and then you kind of socially engineered, hacked your way to get an opportunity to showcase your skills.
4
SPEAKER_02
And I want to highlight that because I think a lot of people are like, oh yeah, you know, you just, you hack your way to the top.
4
SPEAKER_02
And it s like, well, not really.
4
SPEAKER_02
You still got to back it up.
4
SPEAKER_02
I still had to do the jokes.
4
SPEAKER_02
Yeah, you still had to go up there, like you might have hacked an opportunity that other people, you know, trying to wait in line, you know, are thinking like, oh, these guys are, you know, they re suckers, they re doing that, or, oh, yeah, you know, I m just hacking a lucky break, but you could have just as easily gotten up there with no skill and then totally blown it, and they re like, who let this guy on stage?
4
SPEAKER_02
Get outta here, man, I don t wanna see you here anymore, right?
4
SPEAKER_03
I feel like you still have to deliver.
4
SPEAKER_03
I feel like people like that,
4
SPEAKER_03
we re going to make it anyway.
4
SPEAKER_03
That s why people get mad at these Vine and these Instagram stars or whatever.
4
SPEAKER_03
Can you believe the dude don t do nothing on Vine and he got all this money and opportunity?
4
SPEAKER_03
There s a lot of them that are really talented that they were going to make it whether it was 1991 or 2017.
4
SPEAKER_03
They were going to be fine because the talent is there.
4
SPEAKER_03
They just figured out a way to use the platform to hack their way to the front of the line.
4
SPEAKER_03
And I m not mad at them.
4
SPEAKER_03
It s no different than what we used to do.
4
SPEAKER_03
Another way I used to get booked at a lot of comedy clubs, I would manipulate their media.
4
SPEAKER_03
I learned a lot in my time in morning radio and I learned how certain markets operate and I started and there was a radio website I would go to
4
SPEAKER_03
where you could literally break down each market by ratings and specifically by station.
4
SPEAKER_03
So you could pull down every single market and know what the top 10 stations are in that market.
4
SPEAKER_03
So I would look at that list and I would compare that list.
4
SPEAKER_03
I would go find cities that I wasn t booked in.
4
SPEAKER_03
And then I would look at the radio markets in that city.
4
SPEAKER_03
And then I would look and see which radio stations the comedy clubs advertised with in that city.
4
SPEAKER_03
The goal was to find morning shows and afternoon drive shows, which are the highest rated shifts, and FM radio.
4
SPEAKER_03
To find markets with morning shows and afternoon drive shows that were not syndicated.
4
SPEAKER_03
Because that means if you re working in a market like, say, Fort Wayne, Indiana.
4
SPEAKER_03
Fort Wayne, Indiana at the time.
4
SPEAKER_03
Shout out to Weasel, who used to be there.
4
SPEAKER_03
He s gone now.
4
SPEAKER_03
Weasel was a guy that had, it was a two man morning show.
4
SPEAKER_03
It wasn t syndicated, which means that their programming director probably isn t spending a lot of money on content.
4
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Everybody loves content.
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Everybody even loves even more, they love free content.
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And in radio, when you re a content provider, you generally provide what s called a barter for the listeners who don t understand the concept.
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I m a content provider, and I provide to you a prank phone call, or a silly sketch, or I call into your show and do voice work.
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I m a voice actor.
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In exchange,
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you barter my company two ad spots during that shift.
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So an ad spot during morning and afternoon drive could cost anywhere from $50 to $100.
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So as a radio station, you re essentially losing $200 every time you run this sketch in the morning because you have to give me two commercial spots.
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And that s two commercial spots you could have sold, but you can t sell them because you owe me for the voice work that I m doing on your show.
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So once I learned how to barter system work, I tried to figure out a way to hack that shit.
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So I would contact radio stations and markets where I wasn t performing and I would offer them content for free.
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And so what I had at the time
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we were doing an average of 200 prank phone calls a year.
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And by the time I figured this out, I had a bank of maybe four or 500 prank phone calls before the hard drive crash up there.
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And so I would put three or four pranks on a CD with a nice presentation package, and I would show you your numbers, and I would show you what your competition was doing, full color printing, the whole lot.
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And I would mail it to these radio jocks in these markets and I would give them three weeks to reply.
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If you didn t reply, I went to the next station on the list per your market.
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I probably scooped up 40 markets over the course of six months that were running my prank phone calls once or twice during their shifts.
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Wow, 40 markets.
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That s a ridiculous number for
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somebody to pick up and basically just grinding it out.
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You made a plan, you made a list, you sent all this stuff out and did the legwork.
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I mean, to have that kind of success rate, you kind of cracked the code with this.
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Now I sent out probably 250 to 300 packets.
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So the other reason why markets were picking me up is because I said, I don t want any barter.
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You can keep your spots.
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All I need you to do in exchange for running my prank phone call is say my name and my website.
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That s all I need you to do.
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Say my name, say my website, and you can play them as many times as you want, whenever you want.
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That s the other thing.
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A lot of show prep services, as they re called,
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that create content for radio, there s a limit to how many times you can run something or the frequency and all of that.
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I didn t give a damn, man.
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Just say my name when you play it.
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Keep your $200.
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So as a radio station, you re getting free content and you can play it as much as you want and you re basically saving $1,000 a month.
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That s $12,000 a year.
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That s a part-time shift.
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I ve literally created an employee at your company.
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So I would let that sit for three months.
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And then I will contact the comedy clubs.
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and I d go to these club bookers and I d send them the same VHS tape I sent with the same facts and the same follow-up email, then I would send a link to me being on the air in their market.
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So to me, a lot of the cities that I started booking, I probably, out of the 40 markets I was in, I got booked in those comedy clubs and still work them to this day in about, I d say 12 to 15 of those markets because I had a radio presence.
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And I know I am because I did the research on the fucking website.
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I m the only comedian contacting you to get work that is currently on the radio in your market.
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So that s free advertising.
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You d be stupid not to book me.
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It would literally be stupid to not take advantage of this free advertising because when I come in town now, when they play my prank, they re going to say I m performing at your club.
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Got it, got it, okay.
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So you got real estate on the radio, that generated brand awareness, and then at that point it was, okay, now say he s performing at XYZ.
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So of course the club s gonna book you, because not only are you coming in and they re going, ah, you know, all these comics are a dime a dozen, we can book whoever we want.
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You re like, as a bonus, I come with five grand and free advertising for your club.
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Exactly, you have to add value.
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You have to figure out a way to add value, and so,
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I didn t really put it together as what I was doing then.
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To me, it was just, I m just trying to work this market.
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And I know you value comics for on the radio, because at the time, and even now, the Tom Joyner guys and the Bob and Tom guys, oh, you booked them because they re on the radio.
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So you value radio as much as you do a television credit.
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Well, it s easier to get a radio credit than a TV credit, so let me go do this station.
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And that s what I would do.
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And the jocks, God bless them.
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They held good to their promises.
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There was no contracts.
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Right.
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You have a lawyer is a gentleman s handshake.
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But they respected me for being on the like.
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There s a brotherhood.
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radio.
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Hey, I m on the radio in Birmingham.
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I see you guys up there in Fort Wayne.
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If you need a couple pranks, let me know.
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I ll send them your way.
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Just plug my website.
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And at the same time, that built traffic to my website, and people download the pranks and send them around.
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This is back when going viral was over email.
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People would send you a email attachment, go, trust me, it s not a virus.
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It s funny.
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Unreal, and then did things start to snowball?
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I mean, you hit Letterman in 2006, Last Comic Standing in 2010.
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Is this when stuff started to snowball, or is it only a snowball in hindsight?
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I d say the snowball might be now.
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Well definitely right now.
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Yeah, I mean honestly to go from You come off a cancelled sitcom
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And you roll that into the daily show, which rolls into a one hour special, which rolls into opening more doors and opportunities with the network.
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Like, to me, that s unfathomable.
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You know, every year I look at as just, all right, it was a little bit better than last year.
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Like, I never had that, like it was never in a flash, you know?
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Because, yeah, I did Letterman in 06, and there were still comedy clubs who wouldn t book me.
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So what s that worth, you know?
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You re on Letterman, you can t get booked at a stinking comedy club?
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There s certain clubs that wouldn t promote me.
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There s bookers that, to this day, I don t work for because of that.
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Because when you re a feature act, and you re working your way up to headliner, they tell you, well, I want to headline you, but you don t have enough credits.
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and you go get the credits, and then they go, well, we can t book you.
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That s, you re a liar.
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You know, I always had opportunities to skip a level or do more, and Letterman helped.
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That got me in some markets.
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Colleges were immensely key for me in terms of being able to,
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Fiscally viable, like colleges pay enough to let you do the stuff that doesn t pay because you have to stay in L.A.
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a little more and audition.
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Right.
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You know, I was making more money and had more opportunities after Letterman.
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But then I moved to L.A.
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and my rent went from five twenty five a month to twenty one hundred.
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so are things better or are you just it s just a new set of challenges like that s how I ve always looked at it and I don t for one second take for granted anything that I ve you know been blessed with have been able to achieve but for me it s like every year it s just a strategic build on the year before and a year after I you know I d say probably the toughest year
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was after I had done Sullivan and Son on TBS.
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So we ran for three seasons, got canceled after 2014.
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So for me, 2015 was about figuring out ways to get more into the sports sphere, because the only two comedians over there is Frank Caliendo and Rob Riggle.
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And they do very well for themselves in that regard.
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So I go, okay,
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Maybe there s more real estate over there for comedians and sports.
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So I was trying to kind of work that angle and it s been very difficult.
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And you re still doing your club gigs and your colleges and you re making money and you re paying your bills doing comedy, which back in 98, that was all you ever wanted.
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But now it s 2015 and you go, this ain t enough.
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There s gotta be more, what more can I be doing?
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It s hard to figure it out when you perform beyond the goals that you had originally set for yourself.
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Because it s such a new territory.
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Yeah, uncharted territory.
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Yeah.
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Yeah.
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And thankfully, Conan O Brien, I m forever indebted to that man because he put me on TV a lot of times when a lot of other people wouldn t.
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I only did Letterman once.
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I only did Ferguson once.
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When I look back and it s like, yeah, it was great.
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But to have the repeated opportunities to stay on television, that becomes the new headache.
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It s like, oh yeah, you did Letterman, your life s made now.
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It ain t 1994, man.
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Late Night is a wonderful supplement to an established career or can help begin and help a comic establish a career, but I believe gone are the days of a comic doing one Late Night set and turning into Ray Romano.
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Just the landscape is too different now.
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I did Letterman, sure, yeah.
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And then I did Ferguson.
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And then I did Conan.
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And then I did Live in Hollywood with Kiki Schroeder.
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And then I did a sitcom for 30 episodes.
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Then I did Seth Meyers.
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So it s that constant treadmill of being out there and being seen and making sure that your writing is staying fresh enough to maintain that presence.
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That becomes the new challenge.
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I m blessed enough with an opportunity in promoting this special to have done Jimmy Fallon.
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Cool, blessing, but can you get back?
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So now the thought becomes, all right, what s the next five minutes I can do if ever I get a chance to get back on Jimmy Fallon?
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Because it s important, visibility is important now more than ever in comedy, because it used to be I was just competing with other comedians.
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Now you re competing with the internet, you re competing with YouTube, you re competing with 900 channels on cable.
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To be able to make some noise that rises above all of that,
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It s paramount and I ll forever be thankful to Conan O Brien because there was a time period in my life where a lot of people said no to me and Conan was the only person saying yes repeatedly every year.
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And that s something that helped a lot, more than I think he realizes.
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You have to keep finding that next thing, because I can look back at Letterman and say, oh, it snowballed.
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But if I look at the time between Letterman and now, there was a lot of worry.
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There was a lot of concern.
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There were a lot of days of, all right, how do I top last year?
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Even now this year, I don t know how I m gonna top this.
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It s only February and I got an hour special dropping and I ve done Jimmy Fallon.
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Got a kid, gotta feed him.
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So that thought process, that fear, that s what drives me.
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So I don t know if I ve ever really registered having made it or having success.
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I do very well.
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I m blessed to have the resume that I have.
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But, you know, people talk about, like, the light in the tunnel.
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It s the only way I know to put it.
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Like, people talk about a light in the tunnel.
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They go, all right, so you keep walking through the tunnel because it s dark and eventually there s a light at the end of the tunnel.
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To me, the light in the tunnel is a train.
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coming from behind to run me over.
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The failure train is approaching.
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So I sprint through the darkness having no clue what I m doing or what s next.
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All I know is to trust my instincts because they got me this far and I m driven more
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by fear of failure than a desire to be at the top of the mountain and be successful.
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And I don t know if that s completely healthy, but it s worked for 19 years.
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So, you know, I don t think I ll change.
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I think
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that you ve managed to do so much and it has taken a long time.
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I mean, you ve been on the grind for a long time.
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I do wonder though, what does go through your mind being on that treadmill like you said for so long?
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What was going through your mind when you got the call to audition for The Daily Show?
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I know you just found out that this pilot you d co-starred in with Whoopi Goldberg wasn t getting picked up.
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You get the Daily Show audition, were you like, all right, I m on, I m on, I m on, or was it like, all right, I m gonna get in here, but I m not gonna get my hopes up?
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What s going through your head?
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What s your mindset for these sort of intense auditions that have a lot riding on them?
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You can t attach yourself to the ending.
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Attach yourself only to the opportunity.
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Without anticipation, there is no disappointment.
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I don t know when I turned the corner, but I detached myself from anticipating and just focused on preparing.
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do the audition, and do well.
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The rest of it you cannot control.
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You literally cannot control whether this network picks this show up, and there s sitcoms that don t get picked up solely because a bunch of suits in a room can t agree on how to divvy up the cash for it.
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Whose fault is that?
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It s not the actor s fault.
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This sitcom said don t get picked up because one of the actors refuses to move to the city where they re going to shoot it.
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And you can t shoot it with a replacement because that actor was the tent pole that was holding up the whole damn thing.
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So what you gonna do?
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You gonna quit auditioning?
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You gonna be sad and let this sadness pollute your process on everything else that you re gonna do?
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I worry about the stuff I can control.
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So, you know, you live, you die.
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Shows get canceled.
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Some shows never get made.
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Be thankful that you got cast and had the opportunity.
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So I went into the audition.
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It s just another audition.
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If it goes, it goes.
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If it doesn t,
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then you stay focused and trust that whatever you did that got you that damn audition in the first place will get you another one.
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Your talent got you to this point where you were even able to fail.
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So
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Celebrate that.
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Celebrate the fact that you had enough of an ability for somebody to even give you a damn chance.
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So, the Whoopi show doesn t go, and yeah, that was disappointing.
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Of course I wanted to work with Whoopi Goldberg.
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Yeah, what was cool was that Ernie Hudson was in the pilot, too.
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I got to meet Ernie Hudson, which, if you re a Ghostbusters fan... Jason is, like, super stoked right now about that.
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No, man, Ernie Hudson, come on, that s cool.
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You know the irony of Ernie Hudson?
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He was the prison warden in Oz on HBO.
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Yes he was!
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All that callback.
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I was like, now the rape scenes!
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How did y all she said, I was never there for those brother.
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I was never there.
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Every time I think of somebody getting raped, I think they just got Schillingered.
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Yeah, and then he played a priest on Law and Order.
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I was like the irony.
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What a turnaround.
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So that sense of auditioning for The Daily Show, man, I left town after my audition.
6
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I did my audition, I went to Junior s Cheesecake, had myself a piece of cheesecake, and I bounced.
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I was back at JFK by four o clock.
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The nervousness didn t set in until the night of the premiere.
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My God, I m trying to think of the most nervous I ve been in my career, like moments.
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My first ever television credit was Showtime at the Apollo.
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In 2001, I did comedy TKO, and you could hear the nervousness in my voice.
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I was pretty nervous for Letterman.
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And then, this is what they don t tell you on Letterman, that black dude Biff, I think was his name, the short black dude that would like do sidekick stuff with Letterman.
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Biff was the one that was pulling back the curtain.
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Before you walk out, right before Letterman says my name, Biff looks me in the eyes and goes, relax, kid.
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It s only your whole career.
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Oh, wow.
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You little motherfucker.
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Yeah.
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He did it as a joke.
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But I walked out like, oh, no, no.
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Wow, because you re like, I was in the zone until I thought about all that.
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I was never nervous for any of the last comic standing stuff.
6
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I got to the semis in 07, and I wasn t nervous.
6
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And before that, I d done Star Search.
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And between the Apollo and Star Search, I d had enough exposure to contest comedy and someone who you don t respect critiquing you and telling you why you re not good enough.
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all of that shit so it kind of rolled off my back and then there was no nervousness when i did last comic i think 2010 when i got third place so NBC made us they made us live tweet it s like the beginning days of live tweeting with the networks and all that
6
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And we had to live tweet under the hashtag last comment.
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And every Monday night, you have to live tweet with people and half of them hate you.
6
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So in real time.
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you are reading people s hateful comments about you.
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I did that every week for like eight weeks, man.
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Every Monday night, there s people that love you, but then you also have to read the worst things ever said about you.
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Because it s live tweeting, we have to interact.
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And so, that galvanized me.
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I d had a YouTube account long enough to see people say some weird stuff to me, but
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Reading that hatred weekend week out for two months straight.
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Yeah, I stopped caring what people think about me anymore like you cannot carry that type of emotion so that just kind of rolled over to auditions and Audition for daily show and I was like all right.
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I did it.
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I wrote my piece.
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I did it who cares.
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I m done I
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Either they like me or they don t.
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Either way, I gotta figure out where the next job is coming from.
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So until it is, it isn t.
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So I don t obsess over what else and what could be.
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SPEAKER_00
It sounds like you manage your expectations really well so that you re not crushed if it doesn t work out.
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But on the flip side of that coin, when you do have an opportunity like that, how do you get excited enough to perform while also managing those expectations so that you re not crushed?
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Because if you re just like,
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man, I don t care what anybody thinks, and you go out there and you just do something, it could actually hamper the performance.
6
SPEAKER_00
You still gotta be stoked about being there, right?
6
SPEAKER_00
And being in the room.
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Yeah, of course.
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And you know, like, the premiere of The Daily Show was probably the most nervous I ve been since the Apollo.
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It didn t really hit me.
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The month of preparation, we did test shows, and you learn how to read a prompter, and you write your pieces, and you know, whatever.
6
SPEAKER_01
But then you walk in the hall the night of the premiere, and it s all the old correspondents are there, and there s tons of media, and you ve got all the execs from Comedy Central, and this is gonna be live, live across the entire Viacom network.
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SPEAKER_01
This shit was on TV land.
6
SPEAKER_01
It was on Nick Jr.
6
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One of the most loved shows is returning to air with a new host, and everybody s dying to judge it.
6
SPEAKER_01
And you gotta stand out there for three and a half minutes and do these jokes, and not flub a single line.
6
SPEAKER_01
But you trust your training, and you trust everything that you ve done up until that point to get you through the moment, and I turned out fine.
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To me, there s an excitement to it, but that doesn t come until afterwards.
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It s nervous energy up until that point.
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I m quiet, I m pacing, I m going through all of my lines and making sure that I m delivering.
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And there s no, yay, we re doing it.
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For me, there ain t none of that shit before I do a show, man.
6
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It s after I ve done it, and it s, yay, we did it, wow, what a rush, it s great.
6
SPEAKER_01
It s like skydiving, like I m not screaming on the way down, I m screaming because I survived.
6
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Like that s the excitement.
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This reminds me of what we hear a lot from, we have a lot of military and special forces guys at our boot camps here in LA at AOC, and we hear a lot of like, yeah, we don t even think about it during the mission, we re just in the zone, and then at the end it s like,
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Wow, that was exhilarating.
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In the moment, super focused, maybe some nervous energy, a little bit into the flow state, and then yeah, boom, back out.
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And now that you re on The Daily Show, do you get recognized a bunch?
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I m wondering, because of course after the Comedy Central special comes out, which by the way is called Father Figure, we ll link that up in the show notes, this is gonna be on another level.
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And of course after this Art of Charm episode comes out, you won t be able to leave the house.
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I don t know if I say I ll get recognized more, but yeah, I do.
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Yeah, there s some people that speak, but it s more meaningful conversation.
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It s not, hey, you the dude from the thing, man, I seen the thing.
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All right, keep doing your thing.
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It s people coming up and, hey, thank you for what you do, and the country, the strength, and you and Trevor, and get us through this.
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You can tell it s one of the first times in my life where I felt like the jokes that I tell matter, and they mean something to people.
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And it resonates in the conversations that I have with people who do recognize me, specifically from The Daily Show.
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And then it might just be somebody, man, you do them prank calls, somebody go whoop your ass.
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All right, dude.
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Yeah, I can see that.
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And the new special I watched, thank you for the screener, of course, really, really funny.
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A lot of race and political humor in the special, which is really timely.
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Is that stuff top of mind for you because of what s going on right now, or has this always been how you roll with the race and political humor?
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It s definitely been exacerbated by the times we lived in in the past year and a half.
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I ve always dabbled a little bit in race, not as much in politics, but politics have an influence on race, so it s worth addressing and talking about a little bit.
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But yeah, I d say that that was definitely, you know, part of it.
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It definitely
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how to influence.
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I didn t really get into much about candidates.
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So, you know, I didn t feel like talking about Hillary and Trump and breaking that down.
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That s such a difficult thing to digest.
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Plus Trump is, he just keeps morphing into something more and more different than what you saw him as last.
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So I shot that in August.
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Half the stuff I would have said about him in August wouldn t even apply to present day.
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Oh, yeah.
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Good point.
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That could have bit you in the ass for sure.
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Do you find all the timely humor essentially easier to discuss because you re surrounded by this on the daily show?
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It seems like you re bathing in all this stuff now.
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You can t escape it.
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Yeah, I feel like that s the outlet for the timely stuff because it has more value there, whereas my stand-up is more about
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the bigger picture and the bigger umbrella of race relations as a whole.
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Also, talking about how these things affect me and my feelings on those things.
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That s more where my stand-up tries to live.
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I try not to make my daily show persona in terms of the topics I discuss on the daily show.
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I try to keep that separate and apart from the type of comedian I am on stage.
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Like, I m not going to go on stage and talk about Trump s travel ban.
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and why it s wrong and all of the deep dive we know.
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you know, but what I will talk about is the experience that I went through at a Muslim protest.
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Like, this was, and I say it jokingly, but it s true, this is the first protest that I ve ever gone to where it was about some shit that didn t concern me.
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Like, that s refreshing.
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Like, as a black person, usually you re at the protest because it s, hey, this is for us, we need to get our stuff together.
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But no, it was refreshing to just be a guest as somebody else s struggle.
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It was just nice to check in.
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and walk around a little bit.
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So the joke is more about the experience as a black person at a non-black protest and how I want to start going to more protests that aren t my own because it s a lot less stress.
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You still get credit.
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You help the cause.
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but you don t have the emotional weariness that you feel when you leave a Black Lives Matter march.
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Like your mood is just different when you leave something that affects you personally, whereas you can go to another protest and just show up and, yeah, you still care.
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Of course you care.
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You re there.
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But there s just something that just separates those two.
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And so exploring that thought process, that s a joke that I m trying to work on now, because to me, that s a deeper dive.
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Because it s about our experiences and how we relate to one another more so than it is solely about the Muslim ban and why it s stupid and the courts and da da da da da.
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Do you feel pressure to be funny when people you meet find out what you do?
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Like if you meet a bunch of your friends  friends or like your girl s friends or something like that, do you feel like you gotta perform a little bit or do you feel like you re letting people down when you just wanna buy a slice of pizza and you re tired if you re not like jovial and friendly and funny?
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No, I don t know what it is about me and my standup but I tend to invoke a different type of energy or where people aren t
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jokey jokey with me like they ll speak like friends and relatives when they find out I m a comedian they ll try and oh hey but what I ve learned is that if you re low energy yet still cordial no one knows what to do with that so you are being polite but you re not being funny
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And that s the trick.
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It s just to be kind and cordial.
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Because, I mean, offstage, I m a very low-key kind of guy anyway.
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I m not always on.
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I m not jokey.
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But then I also wonder if that s kind of because of the type of comedy that I exude where it s more social frustration than just traditional, just jokes about, you know, whatever.
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So
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If you re somebody that really likes my comedy, it s probably because you have an opinion about something in the world.
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So those types of people tend to be a little more conversational and a little more chill.
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And, you know, hey, I just want to say thank you.
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Love what you do.
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Keep doing it.
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Get out of there.
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It s not a guy following me around.
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I was with a friend of mine.
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I won t say which cast member from SNL, but
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There were just people while they re standing on the curb, just taking selfies with the person in the background as if they can t see it.
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It s like a spectacle and they re just waiting on an Uber and you have people hovering but they won t speak and it s just...
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I don t know, it was just very weird.
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It s either that or they re yelling lines at you.
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Like how Chappelle had to deal with people yelling, I m Rick James, bitch.
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And that type of stuff.
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You know, I don t have that type of stuff going on.
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Thank goodness.
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Not yet.
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Special comes out on the 19th.
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Yeah, you got a special kind of charismatic crankiness that I actually feel like will make you even more funny as you get older, which is good news.
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You don t have like that young guy Snapchat comedy.
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You got like a, it s about your opinions.
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It s about the experiences that you have.
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So as you get more of them, it will add to the performance and not be like, oh, this guy s still talking about this stuff.
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Yeah, that s the goal, man, is to make sure that
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what I do is about where we are as a society now, and my opinions about that.
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So yeah, I don t talk about politics per se.
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Like on the special, I don t have time to get into the right and wrong of whether Colin Kaepernick should take a knee during the national anthem.
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To me, that s not the discussion.
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The discussion is about
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Why are you expecting all black people to be patriotic?
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And then from that point, supporting it and showing reasons why black people have never been consistently patriotic as a race.
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And that becomes the issue.
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It s not
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whether Kaepernick s right or wrong, it s me being curious as to what made you think that all black people were patriotic in the first place.
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Like, why did you think that?
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So for me, that s where I like to exist.
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The issue is a catalyst, but the discussion is about something much more broad.
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And that s kind of where I like for my comedy to live.
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Yeah, this is fun, man.
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I m glad we re doing this now.
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I m bummed I waited so long, but it doesn t really matter.
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I mean, now s the perfect time, so.
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I m thankful that you even still care enough to have me on, man.
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Oh, absolutely.
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And by the way, you guys are killing it, man.
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I watch it every morning when I get up with my coffee.
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I watch The Daily Show and I watch Ad Midnight.
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Those are my two, like, go-to s.
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Amazing.
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Like, every morning.
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And it gets me in a good mood for the day.
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I appreciate it.
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I appreciate that.
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Roy, this was super fun, dude.
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Thank you again for your time.
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Alright, you guys.
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That was so good.
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He s funny, but he knows how to be serious, and he has that confident, charming crankiness that makes him a really good comic.
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The timing is really good.
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I mean, he was walking the walk, and he s just a talent, man.
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No, no doubt.
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That was so much fun.
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That was one of the most fun shows I think we ve ever done, because I ve always wanted to have the behind-the-scenes of what it takes to be a stand-up, and this really delivers on every front.
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Yeah, we gotta go hang at The Daily Show next time we are in New York and go hang with Roy.
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He does really funny segments on that show as well.
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And of course, the special will be linked up in the show notes.
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We ll link his CD in the show notes as well.
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So a great big thank you to Roy Wood Jr.
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We ll have his Twitter in the show notes as well.
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And if you enjoyed this one, don t forget to thank him on Twitter.
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And I m also on Twitter, at The Art of Charm.
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Remember, if you wanna see the show notes for this episode with all those links, you can tap your phone screen, your iPad screen, whatever you re using to listen to this.
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We ll link to the show notes right on your phone.
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Like I said, I m also on Twitter.
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It s a great way to engage with me and the show.
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And Jason, you re on Twitter, too, at JPDEF.
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Am I right?
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You are right, sir.
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All right.
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Boot camps, our live program details, those are at theartofcharm.com.
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Join thousands of other guys who ve been through the program.
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They ll be your network for life.
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We got a lot of people traveling around the world, hanging out with their alumni buddies.
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The live program is amazing.
7
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It s super rewarding for us, and of course the idea is to make it super rewarding for you as well.
7
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I love seeing how far people take this with their own grit, their own drive, their own Roy Wood Jr.
7
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type grind to make it happen and change their lives.
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I also want to encourage you to join us in our AOC Challenge.
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That s theartofcharm.com slash challenge.
7
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It s about improving your networking skills and your connection skills and inspiring people around you to develop a relationship with you.
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We ll also email you our Fundamentals Toolbox that I mentioned earlier on the show.
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That includes the practical stuff on the body language, the charismatic nonverbal communication, the attraction stuff, the negotiation stuff, networking and influence strategies, and everything else that we re teaching here at AOC.
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I m also doing regular videos with drills and exercises to help you move forward.
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The idea is the challenge will make you a better networker, a better connector, and a better thinker.
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That s the rcharm.com slash challenge or text charmed, C-H-A-R-M-E-D in the U.S.
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to 33444.
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For full show notes for this and all previous episodes, head on over to theyardofcharm.com slash podcast.
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This episode of AOC was produced by Jason DeFilippo.
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Jason Sanderson is our audio engineer and editor, and the show notes on the website are by Robert Fogerty.
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I m your host, Jordan Harbinger.
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Go ahead, tell your friends, because the greatest compliment you can give us, well that s a referral to someone else either in person or shared on the web.
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Word of mouth is everything.
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So stay charming and leave everything and everyone better than you found them.
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Thanks for listening to the Art of Charm.
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Get more confidence, relationship skills, life hacks, and more at theartofcharmpodcast.com.