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The five hardest questions in pop music

Paisley Park, Prince's private estate and production complex in Chanhassen, Minn., is lit with purple lights at night. MUST CREDIT: Washington Post photo by Michael S. Williamson.

It's a cruel world. Here's why being a virtuous music listener feels harder than ever.

Whenever a teacher or professor invites me to their class to speak about my work as a pop music critic, I jump at the chance, eager to blab with students about whichever songs might be lighting up their brains that week. And while I've been making classroom visits for years, I've never felt sufficiently prepared for certain questions that always seem to materialize - questions about cultural appropriation, problematic lyricism, selling out, the ethics of posthumous listening, and the slippery white whale of 21st-century cultural criticism, "separating the art from the artist."

Part of what makes these questions so vexing is our desire to answer them decisively, as a unified, monolithic listening public. But how do we even begin to answer them as individuals? A few months ago, I promised one group of students that I would give it a go. Here I am.

And here we are, living in an era in which listeners expect their favorite musicians to reflect their personal values and politics in neat, legible, completely literal ways. We demand that our pop heroes be virtuous in their private lives, valiant in their public art - and if they aren't, we try to compensate by being ethical in our listening. And we expect the same of our peers, so we patrol neighboring fandoms on social media, as if music were no longer something we each experience privately inside our heads.

Still, music remains as private and mysterious as ever, and while some view music criticism as a clarifying force, I would much rather try to put people in touch with the mystery. That's another way of saying that I don't have foolproof answers to the five hardest questions in pop music - only tactics to better cope with them. Here they are.

1. Is cultural appropriation ever okay?

I was recently hanging out with a rock band, discussing our shared love for a particular R&B album. They said they'd love to cover the album track for track, but would never. A band of white indie-rockers performing the songs of a black R&B singer? No way. It would be seen as cultural appropriation, and their reverence for that music was probably better expressed through conversations like the one we were having that night anyway. As badly as I wanted to hear their covers, they were right.

When is cultural appropriation - the act of making art that reaches for new ideas across lines of race and class - ever acceptable in pop music? Finding an answer requires us to clarify the difference between theft and influence, or more specifically, taking and making.

When Justin Timberlake beatboxes, or Taylor Swift raps, or Miley Cyrus twerks to a trap beat, it feels like taking. Nothing is being invented other than a superficial juxtaposition. On the flip side, when the Talking Heads echo African pop rhythms, or the Wu-Tang Clan channels the spirituality of kung-fu cinema, or Beyoncé writes a country song, it feels more like making. The borrowed elements become an essential, integrated part of a new, previously unheard thing.

We think we know this difference when we hear it, but sometimes we don't - so there are more questions to ask, and many of them point toward an imbalance of power. Is the appropriating artist profiting off a culture that remains marginalized? Does the appropriator seem to understand the complexity of their own relationship to the culture they're cribbing from? Will their appropriated music steer attention toward its source? Or will it divert potential attention away from it?

White rappers are by far the most flagrant appropriators on today's pop charts, and many of them flunk these questions. Yet, scores of mediocre white rappers - from Iggy Azalea to G-Eazy to Post Malone to Bhad Bhabie - continue to climb far higher in the marketplace than they would if they were black. This falls on the audience and the industry. For these artists, it's not that their whiteness automatically makes them bad rappers; it's that their whiteness automatically sets them up to become successful rappers.

Here's one last question that might be helpful to ask of white rappers, or any musician who appropriates: Are they travelers, or are they tourists? Travelers move through the world in order to participate. Tourists simply look around, have some fun, take what they want and bring it back home.

Which brings us back to the indie-rock band in love with the R&B album. They knew they weren't going to perform these songs at next summer's Essence Festival. Their covers wouldn't transcend tourism. So they stayed home.

2. Should we listen to music against a dead artist's wishes?

Everything about Prince's death felt unreal, including the fact that the single greatest musician of our time vanished from this world without leaving a will. Maybe he thought he was going to live forever, just like the rest of us did.

What Prince did leave us, however, is a knot of anxiety over how to approach his body of recorded work. Would he really want us streaming his albums on Spotify, the very type of hyper-corporate, artist-unfriendly music distribution system that he spent all of his purple life railing against? And what about the contents inside his mythic vault? Would he have wanted us rifling through the recordings that he had so purposefully locked away in the depths of his Paisley Park studio?

I believe that vaults are meant to be cracked open - and even if they weren't, it's ultimately a musician's responsibility to be clear about what should happen to their music when they die. If an artist doesn't want a particular recording in circulation once he's gone, he should destroy that recording himself, or at least leave explicit instructions for his executors in regards to the shredding. Otherwise, that music will find its way out into the world.

But "the world" and "the sales floor" are two very different things, and I know I'd feel much better listening to Prince's unheard music via the Library of Congress or the Free Music Archive than on a commercial streaming service. In September, I'll have to decide exactly how to listen once Prince's estate releases "Piano and a Microphone 1983," his first posthumous album from the vault.

Paying cash money to hear songs that Prince may not have wanted us to hear in the first place might flash us back to the unfinished Michael Jackson recordings that L.A. Reid finished off in 2014, or those private Kurt Cobain demos that surfaced a year later. The listening might feel good on our ears, but the money changing hands will inevitably feel gross.

That's one of the ugliest downsides of the streaming era. When we stream music, our listening becomes transactional. And surely, that drove Prince crazy. To honor his memory, I continue to listen to his albums on vinyl and CD, and I sleep a little better at night.

3. Can today's artists still sell out?

Remember the '90s, back when a mere whiff of corporate affiliation could permanently vaporize a musician's good public standing? The idea was that corporate involvement automatically fouled the human connection between the artist and the audience, and if a musician was foolish enough to dabble with such dark forces, they were swiftly banished to the valley of the sellouts.

That kind of excommunication seems impossible today, even surreal. Selling out is a thing of the past. How did we get here? It started when a new generation of entrepreneurial rap stars figured out that a lot of money was being made in their names, and they wanted to be the ones to pocket it. The human connection stayed intact because their refusal to be exploited felt entirely relatable.

Now, corporate sponsorship has become a validating force in popland, where artists are routinely praised for thinking of themselves as brands. The valley of the sellouts has been transformed into a luxury resort where Kendrick Lamar can use his political clout to sell Reeboks, Chance the Rapper can use his quirk to peddle Kit Kat bars, and Bruno Mars can deploy his affable pseudo-funk in the name of L'Oreal hair care products, Hershey's chocolate, J.C. Penney back-to-school clothes and everything under the roof at Walmart.

Even more egregious are U2 and Jay-Z, who have used recent albums to cement partnerships with massive technology conglomerates. In 2014, U2 unveiled its "Songs of Innocence" at an Apple product launch, implanting the album into the iTunes libraries of half a billion Apple customers without their consent. A year earlier, Jay-Z released "Magna Carta . . . Holy Grail," a rap album that initially took the form of a data-collecting Samsung app. Was it any coincidence that these were some of the most empty-calorie recordings of their respective careers?

Alarms should go off whenever music's primary function is to sell another product, but our bigger worry should be over whether that relationship is changing the shape of the music itself. As individual listeners trying to survive late-capitalism, we can always measure our human investment in pop music by asking: Does this song remind me that I'm a human being, or does it remind me that I'm a customer?

4. How should we engage objectionable lyrics?

When I tell people that rap is the most consequential music of this century, there's a question I frequently hear in return, usually from the very young and the very old: "How do you excuse all of the violence and misogyny in the lyrics?"

For a while, my answer was that we always need to listen to music on its own terms, and when we listen to rap, it's important to remember that we're usually listening to marginalized voices who might be trying to exert power over their lives however they can. That doesn't make certain lyrics any less disagreeable, but it does begin to explain why they exist in the first place. And it's important to understand the circumstances that produced the work.

The music critic Simon Frith once wrote a helpful line: "To articulate a sensibility musically is not to endorse it." If we extend that idea to the lyric sheet, does it mean that artists (of any genre) can make violent music without advocating violence? Can they make sexist music without advocating sexism? Before long, we've found our way to that old Chris Rock joke where a woman is out dancing in a nightclub, happily rapping along with a song's degrading hook because "He ain't talking about me."

Who's he talking about? And who's being hurt? Our anxiety over objectionable lyrics tends to be an anxiety about other people. Because no, immoral lyrics will not suddenly make us do immoral things - but we perpetually worry that they offer some kind of psychic shelter to immoral listeners. We know that a song lyric won't weaken our own virtue, but we don't trust those around us to listen as ethically as we do. In that case, we should speak out against the forces that animate whichever lyrics we find objectionable. But I think we can still do that without disavowing the music altogether.

Here's an easier way to think about it: We are allowed to feel more than one way about a particular piece of music simultaneously. When we're truly listening, we should probably feel a few different ways. 

5. Can we separate the art from the artist?

So you just found out that your favorite pop act doesn't share your politics, or that they've said something hateful about a marginalized group of people, or that they have a history of sexual misconduct, or that they have a history of physical abuse, or that they have a history of both, or all of the above.

The more heinous a musician's transgression, the more painful the fan's trauma - because when an artist we admire suddenly does something intolerable, we start to lose our grip on the art itself. It's as if all of that good music was somehow made in bad faith. Music is an act of empathy, right? How could a musician with such an intimate understanding of the human condition choose to violate someone else's humanity so heartlessly?

So we try to let go of the songs, but it hurts. Can we publicly denounce a musician for their misdeeds without abandoning our connection to the music they've made? If you want to try, here's one way.

There are two singers. Both are accused of abuse, and by many accounts, both have done lasting harm to vulnerable people. Personally, I think one singer makes totally banal music, so it's easy for me to be self-righteous and never listen to him again. (The buzzword people have been using lately for this is "canceled.") The other singer, however, has written songs that I've loved for many years, and while I've never really doubted his guilt, removing his music from my listening life has proved difficult.

I obviously don't want this person to receive any more of my money, so I won't stream his back catalogue, I won't buy his new recordings, and I won't shell out for another concert ticket. On top of that, I won't play his music in public. I won't talk about his music with friends, and if his name comes up, I'll be sure to talk about his alleged crimes. If one of his songs comes on the radio, I'll change the station. If a DJ plays one of his songs in the club, I'll flash a thumbs-down and walk off the dance floor.

But I haven't thrown my old CDs into a pyre. In fact, I still listen to them. Alone. And when I do, I don't forgive this singer for the things that he's done. If anything, I hope that chewing on his crimes inside my mind might somehow help me better comprehend the endless injustices that continue to sprawl across the outside world. Maybe that's hoping too much. But I don't think we can ever truly separate the art from the artist. All we can do is separate the art from the world outside our heads.

Author Information: Chris Richards has been The Washington Post's pop music critic since 2009. Before joining The Post, he freelanced for various music publications.