Dave Chappelle Sets The Record Straight On Why He’s Mad About Key & Peele (Video)

As tickets are now available to Dave Chappelle’s August New York City residency shows, the actor and comedian appears on Sway In The Morning. In a two-part video interview, Dave opens up about how Hip-Hop music and specific MCs have affected his life and business. Heather B also recalls Chappelle fiercely challenging her to a freestyle battle when she was running with M.O.P. and Gang Starr. Perhaps most significantly, Dave clarifies the shots he’s taken at Key & Peele. The target is not what it seems.

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In part 1, just after the 20-minute mark, Sway asks Dave about his apparently disparaging comments aimed at Keegan-Michael Key and Jordan Peele’s show. In October, he told an audience at Bryant Park, “You guys don’t know what I’ve been through, watching Key & Peele do my show for the last five f*ckin’ years.” A similar jab came on one of two subsequent Netflix specials.

“I did do that,” he admits. He then tells Sway that he’s yet to see them in-person. “No. But I’ll tell you this, and I’ve said this publicly: I’m not mad at [Key & Peele] at all. That was more a jab at the network because I know what I fought to do with Chappelle’s Show. I know how they resisted the formula that ultimately became the show. Then I watched them parcel it out to all kinds of different comedians. ‘We’ll try it with this one; we’ll try it with that one.’ They did everything but what I think could have been correct. They could’ve got me back. But it’s not a slight against them. Matter of fact, Jordan Peele’s [Get Out] movie is a f*cking masterpiece. Yo, I loved that movie. [To Donnell Rawlings] Donnell, you were my witness – I had a Get Out party. I did. We rented a movie theater. We got Get Out. We put a PA system and we heckled the movie like Mystery Science Theater 3000, and it was great. Everybody was sh*t-faced; it was real late at night. It was after a show, and it was really fun. It’s why I’d go to the movies, to see sh*t like that. I like the work that they do, and I respect the work they do, and I respect them.” Sway asks Chappelle if he’d be open to collaborating with the duo. “Sure,” he answers. “If the situation was right, I’d do all kinds of sh*t.”

In the Sway In The Morning studio, D.B. asks Dave if he draws comparison to younger comics not respecting forefathers, as has been the case with Hip-Hop. D.B. uses rappers like Kodak Black and others discrediting Tupac Shakur and The Notorious B.I.G. to illustrate his question.

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Dave replies, “Nah, I don’t care about that. You know why? Because comedy’s a weird genre. Deep down, I know that every comedian thinks that comedy is all about them. Every single one of ’em! For a comedian to stand in the back of the room and watch another comedian, it’s almost like watching somebody f*ck your girlfriend. And you’re like, ‘Yo; I f*ck her better. You’re not doing it right.’ It’s awful; you get jealous. You’ll hear people hate on [each other]. Kevin Hart is a wonderful person. There’s nothing wrong with him, but guys feed themselves this kind of gunpowder because comedians are insecure people a lot of times, socially-awkward people a lot of times, and a lot of these guys are f*ckin’ miserable dudes. And they need to believe that [they are the best]. Some of ’em vocalize it. Some of ’em don’t. But many of them feel that way.”

Other highlights from Part 1 include Dave calling Sway’s 2013 interview with Kanye West “one of the greatest moments of radio” (11:00). He details the hilarity of the slow-boiling buildup to the “How, Sway?” outburst from two of his friends.

Of his Netflix deal, Chappelle is brutally honest surrounding its benefits. I’ve been balling; I’ve been having a swell time,” he says. Later he adds, “The best thing about money is it’s given me a false sense of security. But a false sense of security is better than no security.”

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Throughout both parts of the Sway In The Morning appearance Thursday, Dave bemoans smartphones for comedy and society. “Comedy is top genre because of how we engage the audience. It’s a very confrontational genre.” He later states that he feels more people are “curating” than actually “living,” all through the small screen.

There is a lot of discussion about the craft of comedy. Donnell Rawlings recalls his days as an emerging Washington, D.C. comic. One night, when he was paying dues with a late-night slot, MC/DJ Biz Markie made a surprise stand-up appearance. The Juice Crew member (who was once a featured recurring guest on In Living Color) killed, making Rawlings have one of the worst sets in memory.

At 19:00, on the subject of battling and competition, Heather B calls out Dave. She admits first meeting Dave following a Real World reunion taping. Years later, after she attended one Chappelle’s Show taping, the stand-up put her on the spot.

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“We’re hanging out [at the hotel following the taping], having a good time. ‘Oh sh*t, Heather B – “All Glocks Down.” Let’s battle right now.’ I looked, and all of a sudden this heat – f*ck a dry-mouth – a heat came over my body. He was like, ‘Lock the doors, you’re not leaving until we freestyle on stage.’ I was just like [shakes head nervously]. He was like, ‘You sucka MC!’… you suck, Dave.” Chappelle shrugs and he responds with, “We have a good time, you know what I mean? We had fun, man. I miss doin’ the show sometimes. I don’t know that I could do it again. The hours… and then the context is so different now. There was no smart-phones then.”

In Part 2, Dave discusses the guests tied to his residency. In particular, he praised Arsenio Hall, who will appear one night. Chappelle highlights his FOX-era devotion to putting great Hip-Hop on television. He also credits him as the first Black comedian on mainstream TV with a show of that kind. “The fact that he’s gonna touch the stage with me and rock, I’m very excited about.” Of Yasiin Bey, he admits “[He was] very hard to secure, but I’m happy Mos [Def] is comin’ back.” It is slated to be one of the Black Star MC’s final concerts in a 20-plus-year career.

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Right before 5:00, Sway asks Chappelle who some of his greatest MCs are, both now and forever. Dave responds, “I believe that if Biggie Smalls had lived a little bit longer, we would get an honorary English Lit degree. Some of the techniques that he employed in his music, I was very, very impressed by, [his narrative]. Lil Wayne, to me, is one of the most clever mothaf*ckas, ever. I do all those jokes about ‘p*ssy juice,’ but I f*ck with that dude! He’s just clever and fun to listen to.”

He continues, “There’s so many good guys. There’s Jay [Electronica]; I like him. Kendrick [Lamar] is killing it right now. Like, some of the sh*t he puts out sounds like pure, uncut adrenaline. There’s certain records from the ’90s [like] when [JAY-Z] was poppin’. I remember listening to JAY-Z before I’d go into meetings with white people to feel confident. ‘I’m focused, man!’ I’d go in there and murder [it]. Even though some of the subject matter was controversial or whatever, the sentiment of the music raised us from boyhood to a man. I’m very excited about Jay’s [4:44] droppin’. He’s 47 [and relevant]. He’s survived and he’s in the center of the winner’s circle…our whole generation was the thrill of victory and the agony of defeat. That was a good moment for me.”

August residency also commemorates Chappelle’s 30th anniversary in stand-up.