Election week is a tense, uncomfortable time that divides a country and can cause even the most innocuous political commentary to suck the levity out of any room. Lorne Michaels served the country well however, by booking the great Dave Chappelle to host SNL this weekend to bring laughter to us all.   In addition to the gift of Chappelle, SNL also scheduled A Tribe Called Quest to be the musical guest, fresh off the release of their new and final album, We Got It From Here…Thank You 4 Your Service. The Chappelle Show was a cultural beacon in the early 2000’s. In only 25 episodes, Chappelle’s skits are memorable and often brought up to this day. Chappelle’s Rick James, Prince and Clayton Bigsby have all been immortalized in popular culture but one thing that can be lost when remembering his show is the unbelievable hip hop talent that performed at the end of every show. Some of the biggest acts of the era performed on the show, Slum Village, De La Soul, Ludacris, Cee-Lo Green, Snoop Dogg and the list goes on. In anticipation of Chappelle and Tribe’s big night on Saturday we’ll take a look at 5 of our favorite performances from the Chappelle Show.


Black Star, Season 1 Episode 12

Saturday Night Live has Paul Simon as the most frequent musical performer, The Chappelle show had Black Star. Talib and Most Def each made three appearances over the two seasons. Talib and Mos Def clearly had a relationship with Dave and one of the things that made all of their performances so interesting was how genuinely excited Chappelle would be to witness them perform. Dave’s excitement over his musical guests was always one of the most charming aspects to the show.  It was evident that first and foremost he was he was an actual fan of the acts that he would book. Dave’s fandom hit a fever pitch during the Season 1 finale when Black Star performed together for the first and only time on the program.


Kanye West for Adidas Ready to Wear Fall Winter 2015 in New York

Back in 2004 Kanye was just emerging on the scene while the Chappelle show was one of the biggest cable programs in the world. It seems hard to imagine now but Kanye was absolutely through the roof excited to be somewhere. Chappelle breaks this down hilariously on the Jimmy Fallon show. Chappelle says that West took a phone call during which he announced, “‘Hello? No, I can’t. Because I’m at the edit for the Dave Chappelle Show, watching sketches that no one’s seen before.’ ” West paused for a moment before declaring, “‘Cause my life is dope and I do dope shit,” before hanging up the phone.



Killer Mike, Season 1 Episode 7

Killer Mike was still a relative unknown to the mainstream with a couple of minor hits but his showing on the Chappelle show was inspired. He performed, “Akshon (Yeah)” and after the premiere of the show it opened up doors for him in the mainstream. The performance itself was excellent and full of all the energy that one expects at a Killer Mike show and you can tell that Dave was thrilled to share him with the previously uninitiated.



John Mayer, Questlove and Dave Chappelle, Season 2 Episode 3

John Mayer is often brought up when talking about the most memorable musical guests in Chappelle show history because of how seemingly out of place he was in relation to the other artists. Mayer showed up in a few sketches and then teamed up with Questlove and Dave himself to give one of the funniest musical performances in recent memory. “Dancing for Different Cultures” was hilarious, illuminating and cutting which makes it the perfect encapsulation of the Chappelle show itself.



DMX, Season 2 Episode 2

The bravado and ridiculousness of DMX is something that Chappelle had brought into many of the characters on his show. He had done several stand up bits about DMX and X’s terse, dark lines. DMX brings his signature barking and aggression to the stage much to the delight of Chappelle. It was the first musical guest of Season 2 for Chappelle and the show had much more confidence about it after the success of season 1. The performance from DMX seemed not only to be a statement from X but also from Chappelle, that he had arrived and was going to do exactly what he wanted to do.