Dave Chappelle sat down Tuesday night for an alternately hilarious and insightful interview on The Late Show With David Letterman, marking his first late-night appearance in six years (and his first on Letterman's show in a decade). There's a clear mutual respect between the two comedy legends, as the duo exchange friendly family banter and reflect on their comedy careers. But the most obvious talking point – Chappelle's infamous exodus from Chappelle's Show – dominates the conversation, with the host playfully grilling his guest about walking away from $50 million and a third season.
"Listen, here it is: Technically, I never quit; I'm seven years late for work," Chappelle says, referencing his departure from the Comedy Central show and subsequent, heavily publicized trip to Africa. "I was there for two weeks," he says, bringing out Paul Shaffer's trademark gravel-laugh. "There's not too many good hiding places left in America."
As for the monstrous Chappelle's Show paycheck he walked away from? Well, that's complicated. The comedian admits that "of course" he would love to have the cash – "The only difference between having $10 million and $50 million," he says, before taking a long pause, "is an astounding $40 million" – but also acknowledges Letterman's point that more money wouldn't make him a better person (even if he "might be a happier person").
The rest of the interview is lighter in tone, as Letterman asks about Chappelle's upcoming June stint at Radio City Music Hall (which features solo shows and collaborations with the Roots, Janelle Monáe, Erykah Badu, Busta Rhymes and DJ Premier). Chappelle then reflects back on his first appearance at the New York venue, opening for soul legend Aretha Franklin at age 19. "Looking back on it, I'm sure she didn't choose me herself," he says with a laugh. "It was 15 minutes. I had about 30 minutes (of material) then – I was prepared enough. Was I as good as Aretha Franklin? Nah. But my job was just to get people used to looking at the stage." He also adds, regretfully, that he "skipped the soundcheck, and nobody could hear [me] for the first three minutes."
Turns out there was one Radio City gig Chappelle hadn't announced just yet: a June 23rd date with rapper Nas and a 45-piece orchestra. "I held that show," he says. "It wasn't just about demand. It was an artist that I really wanted to work with – I'm a big fan of the hip-hop music. It's the 20th anniversary of arguably one of the best hip-hop albums ever made. The album is Illmatic; the artist is Nas."
Chappelle also references another hip-hop veteran, Jay Z, saying the rapper's odes to the "Big Pimpin'" lifestyle make him regret his own life choices. "This guy's had more fun on two songs than I've had in the last 11 years," he cracks.