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How has Dave Chappelle never been on ‘Saturday Night Live’ before?

Chappelle as host is the best idea ‘SNL’ has had since Eddie Murphy played Gumby

We wish we had more hands, so we could give this news four thumbs-up.

On Friday afternoon, NBC announced that comedian Dave Chappelle will host Saturday Night Live for its Nov. 12 episode. This will be the former Chappelle’s Show front man’s first time hosting the 41-year-old sketch comedy show, and his first late-night appearance since The Tonight Show Starring Jimmy Fallon in 2014.

Chappelle, 43, has been relatively absent from the spotlight since abruptly leaving his successful Comedy Central show in 2005. He’s performed impromptu stand-ups over the past decade (he was infamously heckled off a Hartford, Connecticut, stage in 2013) and also solemnly appeared at this summer’s BET Awards to honor the late Prince.

With the announcement Friday of his hosting duties for next weekend — during which he’ll be accompanied by the revered hip-hop group A Tribe Called Quest as musical guests — we wanted to run down the five characters Chappelle has to bring back for SNL from his exhaustive catalog of work over the past two decades. (This list is in no specific order.)


Conspiracy Brother

Over the past few years, we’ve witnessed the resurgence of the “Hoteps” in black society. Do you believe that Hollywood is pushing homosexuality on the black community to destroy the black man and family? Hotep. Do you believe that it’s unnatural for a woman to menstruate? Hotep. Are you ashy right now? Hotep.

Chappelle’s character from 2002’s Undercover Brother was the quintessential exaggeration of Afrocentrism, complete with illogical theories such as George Washington Carver creating the first computer with a peanut, and “good morning” being an Anglo-Saxon term for the absence of color … or 1997’s Good Will Hunting being about “hunting n—–.” In a time where we can’t truly trust the feds, Conspiracy Brother is a necessity.

Reggie Warrington

Much like Christina Milian being in 1999’s American Pie or Garcelle Beauvais (Foxy from The Jamie Foxx Show) in R. Kelly’s Down Low (Nobody Has to Know) music video, one could, at the time, forget that Chappelle appeared in the Eddie Murphy-led The Nutty Professor. Reggie, the obnoxious stand-up comic who humiliates Sherman Klump while at the comedy show, took full advantage of the few minutes he had on-screen. Who could forget “Women be shoppin’!” or “He must be on that new diet: Slim Slow.” This character has an even more special meaning now that Murphy told his first onstage joke in 28 years last October.

Clayton Bigsby

Somehow, someway, the sketch about a blind black white supremacist was in the first episode of Chappelle’s Show. Most shows would need a season or two to pull off something so groundbreaking as this crazy premise, but Chappelle shot for the stars with his first attempt. Not only was the 10-minute sketch one of the funniest bits the show put out in its two seasons (we don’t count the Chappelle-less third season over here), it was its most conscious and thought-provoking. In a 2016 election season that has seen the rebirth of white nationalism in the mainstream media, the endorsement of a presidential candidate by the Ku Klux Klan, and former Imperial Wizard of the KKK David Duke appearing at a historically black college, it’s amazing that back in 2003, Chappelle would have the vision — and gall — to put racial commentary front and center on basic cable. Was Clayton Bigsby Chappelle’s most quotable sketch? No (though we’ll never look at Condoleezza Rice’s name the same way again). But it’s one of the more complex looks at American racism that we’ve ever seen on television.

Rick James

The Rick James character from season two blasted Chappelle and the show to the stratosphere of pop culture. Everyone knows what the five fingers said to the face. Everyone knows how James felt about Charlie Murphy’s couch. We know that the milk’s gone bad. In the same vein as movies such as Office Space and Pulp Fiction, the Rick James sketch is a cult classic forever etched into the minds of millions across the country. Chappelle even got the real Rick James to blurt out, “I’m Rick James, b—-” at the BET Awards once. Classic.

Prince

First things first: Rest in peace, Prince Rogers Nelson. While the original “Charlie Murphy’s True Hollywood Stories” with Rick James will go down in history as one of the greatest comedy sketches, the show’s take on The Purple One was what everyone was talking about after Prince’s death in April. From the Zorro-type outfits of Prince and Shalamar, to “assemble your crew,” all the way to Prince’s slow-motion descent back to the ground after a dunk, this sketch still lives in the memories of those who watched. That sketch is the reason for “Game, blouses” that everyone tweets after certain victory in any sport. Chappelle bathed us all in the waters of Lake Minnetonka in just six minutes. Oh, and the whole story was true. That’s the magic of Chappelle right there.

And don’t let us forget: Micki Free is not a girl, aight.

Martenzie is a senior researcher for The Undefeated. His favorite cinematic moment is when Django said "Y'all want to see somethin?"