In college, we used to play a game called “Boots or Shakespeare.” It started out easy: Coke or Pepsi? Swimming or skiing? And progressed onto harder choices: Would you rather be deaf or blind Frozen or burned? Always lonely or never, ever alone?—the idea being that your choices were mutually and permanently exclusive. Once you chose one, the other was off limits for good.

The choices were also supposed to be sort of existential opposites of each other, but I guess I’ve gotten dumber since I left college, because I can’t think of any good examples. Anyway, I knew I had won when my friend James would make the “my head just exploded” gesture.

One stumper for me was: Great songs ruined by bad singers, or dreadful music sung by great voices? Would you rather spend the rest of your life being entertained by the Crash Test Dummies shambling their way through the Gershwin songbook? Or would it be more palatable to hear Ella Fitzgerald try to do something, anything, with aural poo like “Longer Than.”

On the one hand, a good song is a good song, and you could enjoy it on its merits in your head (unless a truly terrible singer ruins it forever, even in your imagination). On the other hand, a good singer is a good singer, and can make something worthwhile out of even the worst drivel (but then you’d have that drivel in your head forever, once the performance was over). Do the prodigious talents of Shane McGowan rescue “Maggie May” from its fearful suckiness? Or is “A Hard Day’s Night” still a great song even though Goldie Hawn found out about it? These are questions for the ages, perhaps better left to people sitting around in the cafeteria putting off writing a Hermeneutics paper.

So you tell me: Is there a singer who’s so good, he’d make anything worth listening to? Or is there a song that you love so well, you’d listen to anyone singing it? In the meantime, here’s some Shakespeare in Boots for you—great songs sung by great voices, perfectly matched. Songs that make you want to sing along, and singers that make you want to shut up and listen. Happy (slightly melancholy, by the way this list turned out) Friday! What would you add to the list? (Some of the videos are kind of stupid, but I went with the ones that allowed embedding.)

Jean Redpath —“Lady Mary Ann”

Billie Holiday—“Body and Soul”


Johnny Cash —“I Walk the Line” 


Led Zeppelin—“Kashmir”


Gnarls Barkley—“Just a Thought”


Creedence Clearwater Revival—“Someday Never Comes”


Fritz Wunderlich —“Die Müller und der Bach” from Die schöne Müllerin


Otis Redding —“These Arms of Mine”