Dave Chappelle sat down Tuesday night for an alternately hilarious and insightful interview onThe Late Show With David Letterman, marking his first late-night appearance in six years (and his first on Lettermans show in a decade). Theres 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 Chappelles infamous exodus from Chappelles Show dominates the conversation, with the host playfully grilling his guest about walking away from $50 million and a third season.
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Listen, here it is: Technically, I never quit; Im seven years late for work, Chappelle says, referencing his departure from the Comedy Central show and subsequent, heavily publicizedtrip to Africa. I was there for two weeks, he says,bringing out Paul Shaffers trademark gravel-laugh.Theres not too many good hiding places left in America.
As for the monstrous Chappelles Showpaycheck he walked away from? Well, thats 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 Lettermans point that more money wouldnt 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 Chappelles upcoming June stint at Radio City Music Hall(which features solo shows and collaborations with the Roots, JanelleMone, 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, Im sure she didnt 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 hadnt announced just yet: a June 23rd date with rapper Nas and a 45-piece orchestra. I held that show, he says. It wasnt just about demand. It was an artist that I really wanted to work with Im a big fan of the hip-hop music. Its 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 rappers odes to the Big Pimpin' lifestyle make him regret his own life choices. This guys had more fun on two songs than Ive had in the last 11 years, he cracks.