Comedians want to be rock stars, goes an old truism, and rock stars want to be comedians. Think about all of the comics — Andy Samberg, Maya Rudolph, Adam Sandler, Jimmy Fallon, Margaret Cho, Jack Black — who love nothing more than grabbing a microphone, guitar or both to live out their rock-and-roll dreams. But the opposite is also true. Here are five musical superstars who not-so-secretly long to be comedians…
Justin Timberlake
So it wasn’t enough to be in one of the world’s biggest pop bands, and then become a number-one-selling solo artist? Apparently not for Timberlake, who’s spent much of the past 20 years trying to convince us he’s a comic cut-up. He’s hosted Saturday Night Live five times, contributed supporting turns in SNL-adjacent comedies like Pop Star: Never Stop Never Stopping and The Love Guru, and took leading spots in Bad Teacher and Friends with Benefits. “If I wouldn’t have been lucky enough to have the profession I have,” he told Entertainment Tonight, “I probably would have gone through improv comedy troupe and school Upright Citizens Brigade and tried to become a cast member on SNL.”
Aimee Mann
In the early days of the Comedy Bang Bang podcast, one could often hear Mann hanging out with the likes of Paul F. Tompkins and Kumail Nanjiani. She’s still part of that same crowd at Largo, the hipster L.A. club where the icons of alt-comedy take the stage. To promote her holiday show, Mann teams up with comedic kindred spirits Tim Heidecker, Michael Cera and John C. Reilly to learn the true meaning of Christmas.
David Byrne
Speaking of Largo, follow its Instagram account to see which cool comics are hanging out on any given night. Just last Tuesday, Fred Armisen was chilling with Sarah Silverman, John Mulaney and… the Talking Heads’ David Byrne?
It shouldn’t sound so weird. Byrne’s musical fingerprints are all over comedy projects like Mulaney’s Sack Lunch Bunch special on Netflix — and just about everything Mulaney-related over the past few years.
Alanis Morissette
Morissette’s comic career began when Kevin Smith dialed her up to play God in his religious comedy Dogma. “It was quite funny for me,” she told MTV. “It enabled me to tap into something, tap into a part of me that I haven’t been able to. My music, a lot of times, tends to be quite serious, but there’s a part of me that’s not serious at all.”
She’s kept honing those comedy chops on shows like Curb Your Enthusiasm, spilling secrets to Larry David and crooning for charity events in a neck brace.
Prince
There are unexpected laughs in all of Prince’s movies, but he really got to show off his comedy skills when he guested on New Girl. This wasn’t stunt casting — Prince not only requested to be on the sitcom but worked on the show’s script as well. Spin called His Royal Badness’ performance, in which he gives love advice, plays table tennis and serves up some delicious pancakes, “pure gold.”