Dave Chappelle Tells Stretch & Bob The Back-Story Of Hosting SNL After The Election (Audio)

Hi. We recently created AFH TV, Ambrosia For Heads’ streaming video service, because we believe real Hip-Hop deserves its own dedicated TV home. But, there are doubters, so, we need your help. If you have enjoyed anything on AFH over the last 7 years, we are asking you to subscribe to AFH TV. It is only $1.99/month or $12/year, and already features some amazing content, but the best is yet to come. Thank you for all of your support.
Hi. We recently created AFH TV, Ambrosia For Heads’ streaming video service, because we believe real Hip-Hop deserves its own dedicated TV home. But, there are doubters, so, we need your help. If you have enjoyed anything on AFH over the last 7 years, we are asking you to subscribe to AFH TV. It is only $1.99/month or $12/year, and already features some amazing content, but the best is yet to come. Thank you for all of your support.

Hip-Hop radio icons Stretch Armstrong and Bobbito Garcia have returned to the airwaves, though in a different format. Bringing their decades of experience and expansive breadth of music knowledge to National Public Radio (NPR), the two men largely responsible for breaking the likes of The Notorious B.I.G., Mobb Deep, and other artists who would go on to change the Rap landscape have today (July 19) launched What’s Good with Stretch & Bobbito. Described by the hosts as “an interview show in which we’re bringing in people who shape the way we think about identity, art, politics, and culture,” Stretch and Bob say, “we’re really trying to dig into the stories that you may not have heard from people that you might be familiar with.”

Skyzoo’s New Video Plays Out A Childhood Dream Of Performing On Stretch & Bobbito’s Show

On the program’s inaugural episode, comedians Dave Chappelle and Donnell Rawlings are featured guests. The topics discussed vary from comedy to politics, with notable moments in which Chappelle reveals some insight that fans could very well be hearing for the first time. For example, at the 7:54 mark, Chappelle discusses his favorite Chappelle’s Show sketch ever done with Rawlings. The first installment of “Playa Hatas Ball,” which starred the two friends, the late Patrice O’Neal and the late Charlie Murphy, sticks out in his mind, he explains. “I think that was, maybe, the most fun I’ve ever had on a sketch,” says Dave.

The interview does, however, include some more serious moments. Taped in his hometown of Washington, D.C., What’s Good lived up to its description when Chappelle was asked how he feels about the city, both past and present. “I do not miss the anxiety of poverty,” Dave says when asked what he doesn’t miss about pre-gentrified Washington, D.C. at the 9:00 mark. “I do not miss the murder rate being the highest in the nation. I do not miss the National Guard policing us.”

Dave Chappelle & Kendrick Lamar Have A Deep Conversation Between 2 Masters At Work

For Hip-Hop Heads, the discussion about Chappelle’s appearance on Saturday Night Live in late 2016 (alongside musical guest A Tribe Called Quest) offers up some backstory commentary of interest. “The experience of doing Saturday Night Live was very difficult for me,” Dave shares at the 17:43 mark. “I was happy to do it. The main reason I did it, I’ve said, is because Phife had passed and Tip had called me and was like ‘this is our last Tribe record,'” he recounts. Clearly, Chappelle placed a tremendous amount of import on the historical value of Tribe’s We got it from Here… Thank You 4 Your service and the legacy of the late Phife Dawg. 

Of course, much of that episode’s significance involved the political climate at the time of its airing in November 2016, when the nation was in the midst of election season and reeling from its result. “I was pretty sure [Donald] Trump was going to win,” says Chappelle. He goes on to say that, in hindsight, he’s pretty sure SNL creator Lorne Michaels was also sure of the then-impending election’s result, “because he was really adamant about me doing the first slot after the election.” He continues, “The night that Trump won,” says Dave, “the writers room at 30 Rock was the saddest place on earth.”

“As a Black American, how emotional do you get about the political landscape? I shouldn’t say it, but it was a Battle of the Whites,” Chappelle says of the Trump-Clinton showdown. “The male White won” [19:40]. Circling back to SNL, he says “it was an enormous amount of pressure, and I was bummed about it. What turned it around for me was that I ran into Louis C.K..” The two, he says, had a conversation that included “two very good pieces of advice.” Firstly, “don’t worry so much about the show, as long as your monologue is good” and, secondly, “don’t do your actual monologue at the rehearsal.”

Dave Chappelle’s 2017 “Block Party” Is Indoors & It’s Going To Be Mos Def

Elsewhere in the interview, Chappelle comments on reports about him that swirled in the days leading up to his SNL appearance. The Daily Beast suggested that the comedian was a supporter of Donald Trump’s candidacy, but Chappelle tells Stretch & Bob that was a “deliberate misinterpretation of what I said,” adding “I thought it was a pretty unethical move. It was funny, because I was actually talking on stage about the ethics of P*ssygate, beyond what we know he said.” Referring to Trump’s infamous words about grabbing women by their genitals – caught on tape and released years later – Chappelle explains he was “talking about the ethics of how we know what he said, about the ethics of secret recording, whether it’s [former Los Angeles Clippers owner] Donald Sterling or Donald Trump.” It was ironic, he says, because he was saying these things while a journalist in the audience was surreptitiously recording him [13:30].

For music fans, though, the final few minutes of the episode are when the discussion hits the sweet spot. Stretch & Bob dive into a segment they call the “Impression Session” in which they play songs and ask their guests to vibe along in conversation. First up is Erykah Badu’s “On & On,” which elicits a memory from Rawlings in which he met Mos Def and Ms. Badu [24:48]. It’s to both of their surprises when she hops on the phone.