Dave Chappelle is hosting Saturday Night Live this weekend. This is a surprise, for various reasons. For one, Chappelle — unlike most folks who host SNL — doesn’t really have a project or product to pimp. Secondly, he has never hosted the show before, so now seems an odd time to start. Finally, Chappelle is among the most reclusive comedians in the game today, so hosting a name-brand program like SNL – particularly coming off the heels of the most contentious election in recent memory – is a unique fit.

But it’s happening, and we’re better for it. Chappelle, who rose to fame via a sketch-heavy show, is a natural fit for the SNL format. And being a stand-up comedian, he will most certainly feed off the juices of a live crowd. And it won’t hurt to have his buddies, A Tribe Called Quest, serve as the musical guests on Saturday night. Hell, Q-Tip – a member of A Tribe Called Quest – once guested on Chappelle’s Show.

He wasn’t the only one. Chappelle’s Show – for all its topical and memorable comedic sketches – was always more a musical show than a comedic one. Like SNL, Chappelle’s Show traditionally featured a musical guest. The show, one of the most popular in the history of Comedy Central and legendary among anyone with a TV and sense of humor in 2003 and 2004, played host to such notable hip-hop and R&B acts as Mos Def, Talib Kweli (twice), Busta Rhymes and Erykah Badu.


If anything, whereas Chappelle’s Show in its infancy gained cred from having the likes of The Roots and Fat Joe on its air, by Season 2, the reverse was almost true. That probably explains why major acts like Snoop Dogg, Big Boi, DMX, and Ludacris showed out for a little sketch program on Comedy Central. Even Kanye West – back when he was transitioning from world-class producer to world-class MC – appeared on the show twice during its second season: teaming up with Common the first time around, and then collaborating with Mos Def and Freeway on one of West’s best tracks, “Two Words”).

Many shows showcase musical guests, and Chappelle’s Show was no different. But it was the way the show infused music into its content that really set it apart from its peers. SNL will occasionally have musical acts double as hosts — think Justin Timberlake, Drake, Garth Brooks and Britney Spears, among others — while other times musical guests will appear in sketches or random one-offs (The Weeknd from earlier this season is an example).


Chappelle’s Show, meanwhile, centered much of its content on either music or a particular musician. Take John Mayer and The Roots’ own Questlove, for instance. On the surface, the two share very little in common musically. Mayer sings pop-rock songs and plays guitar; Questlove plays drums for a hip-hop group. But on a Season 2 episode, Chappelle turned that notion on its head and used Mayer as a way of showing how white folks need little more than some guitar noise in the background to start awkwardly dancing; Questlove was later brought in to show that if black people had a little beat in the background, freestyling was going to result. Chappelle was using music to elicit social commentary.

Other times, he simply used music as a way of conveying a comedic message. There was Roc-a-Pads (from the makers of Roc-a-Wear), R. Kelly’s “Piss on You” music video, Puff Daddy and Making the Band, Wu-Tang Financial, the list goes on. And then there were Charlie Murphy’s True Hollywood Stories.

The episodes ran in back-to-back weeks in February 2004. The first featured Murphy (older brother of Eddie Murphy) recounting his experiences with late wild child Rick James. Words can’t do its hilarity justice. Ditto for the Prince episode, which ran the following week and included pancakes, basketball and Prince’s aura (best to just watch the skit). Both were true stories; James even confirmed his story via interviews during the actual episode. Again, Chappelle’s Show always thrived with music as the driving force.


Many are hoping Chappelle’s hosting gig on SNL this weekend signifies his return to the spotlight, but that seems unlikely. Chappelle seems content to live off residuals, tour enough to maintain his comedic fastball and generally live in peace with his family in rural Ohio. This is fair, and Chappelle certainly doesn’t owe the public a thing; he can live off the first two seasons of Chappelle’s Show and still die comedic royalty.

But there was a time when hip-hop and R&B – and yes, John Mayer – had a mainstream outlet in which to showcase their latest and greatest. Those avenues still exist, but Chappelle’s Show was still an outlier of sorts: a popular, controversial show that technically wasn’t music-centric but in reality was just that. Here’s hoping, for one night at least, we get a return to form for both Chappelle and SNL. And maybe, just maybe, another Prince story.