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Questlove talks about Dave Chappelle’s insane Radio City run

Questlove
Photograph: Michael J. Chen

On August 1, Dave Chappelle will kick off a 16-show residency at Radio City Music Hall, celebrating 30 years in comedy with support from a long list of famous friends. Chris Rock, Chance the Rapper, Childish Gambino and Trevor Noah are confirmed as opening acts for Chappelle throughout the run of shows, but the stand-up marathon will begin with four back-to-back nights featuring hip-hop legends the Roots—a band that credits the comedian with inadvertently helping it land its current late night gig.

“If it weren’t for Dave, [the Roots] wouldn’t even be at The Tonight Show,” bandleader Questlove told us when we caught up with him over the weekend, before the Roots’ headlining set at New Belgium Brewing’s Tour de Fat festival in Chicago. He explained that when Chappelle abruptly left his Comedy Central series Chappelle's Show in 2005, the show’s co-creator Neal Brennan took a meeting with Jimmy Fallon, who was in the early stages of developing his talk show, Late Night, for NBC. “Neal jokingly said [to Fallon], ‘Try to get the Roots as your band.’ What he meant was, the Roots know every musician, so ask the Roots who the best musicians are and they’ll tell you who to get,” Questlove recounted. “But Jimmy was just like, ‘Nah, fuck that, I want the Roots as my band.’”

In the eight years since the Roots began its late night TV reign, the group has collaborated with hundreds of musicians, building on its already formidable reputation as a go-to backing band. Many of those artists are scheduled to join the Roots at Radio City—Chappelle went so far as to dub the band’s four opening sets “Rootsapalooza.” Lil Wayne, Ice Cube, Common, Vince Staples and Big Boi are confirmed to perform with the Roots throughout the week, with plenty of unannounced special guests in the wings. “Our shows are the best ones because everybody and their mother is coming every night,” Questlove said. “They’re coming to us. It’s to the point where we’re rejecting motherfuckers now.”

Why the immense interest in playing just a few songs during an opening set for a comedian? “Dave is the Pied Piper. You always see sports guys and actors co-signing the biggest acts, that’s easy,” Questlove said. “But it takes a real music fan to co-sign the broken toys of Toy Story as his favorite toys.” It’s a stretch to describe the Roots—let alone superstars like Lil Wayne or Chance the Rapper—as “broken toys,” but you don’t have to look any further than the musical guests that serenaded audiences on Chappelle’s Show to see that its creator has always been an outspoken supporter of great hip-hop. Calling in a few favors, even from one of the busiest bands in the business, clearly wasn’t an issue.

After four straight days of high-profile collaborations at Radio City, which are happening in tandem with the Roots’ regular Tonight Show gig, Questlove will be taking a well-deserved break. “I literally never take vacations,” he told us. “I’m taking my second ever vacation of my life after the Dave Chappelle stuff. I’m going straight to Hawaii.”

Take a look at the current lineup (including the just-added shows on August 12 and 22) for each night of Dave Chapelle’s Radio City Music Hall residency below:

Aug 1: Dave Chappelle + The Roots feat. Lil Wayne
Aug 2: Dave Chappelle + The Roots feat. Ice Cube, Common, Vince Staples
Aug 3: Dave Chappelle + The Roots feat. Big Boi
Aug 4: Dave Chappelle + The Roots
Aug 5: Dave Chappelle + Chris Rock feat. Jeff Ross
Aug 6: Dave Chappelle + Chris Rock feat. Arsenio Hall
Aug 9: Dave Chappelle + Erykah Badu
Aug 12: Dave Chappelle live feat. Leslie Jones, Michael Che, Colin Jost and Special Guests
Aug 15: Dave Chappelle + Very Special Guest
Aug 17: Dave Chappelle + Chance The Rapper
Aug 18: Dave Chappelle + Trevor Noah
Aug 19: Dave Chappelle + Childish Gambino
Aug 20: Dave Chappelle + Ms. Lauryn Hill
Aug 22: Dave Chappelle + Solange
Aug 23: Dave Chappelle + yasiin bey (Mos Def) feat. Talib Kweli
Aug 24: Dave Chappelle + Ali Wong + John Mayer + Lil Jon (DJ set)

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