Remembered: ‘Chappelle’s Show’ (2003-2006)

Above: Comedian Dave Chappelle
Above: Comedian Dave Chappelle

How in the hell has it been a decade since Dave Chappelle opted to stop making Chappelle’s Show and took off to Africa?

Seriously? Where did those 10 years go and more importantly, does anyone else desperately wish that Chappelle would make a full-scale comeback? Sure, he’s been doing stand-up shows a little more frequently as of late, but he’s still getting interrupted by knuckleheads that can’t stop themselves from shouting stuff in the middle of his sets and that has kept him from coming all the way back.

Because here’s the thing: Chappelle’s Show was both incredibly entertaining and ahead of its time. All the stuff that makes Inside Amy Schumer so great right now – attacking the industry, addressing stereotypes et cetera – are things that Chappelle was doing a decade earlier.

Here’s a quick look at some favourite segments from the two-season show:

Charlie Murphy’s True Hollywood Stories: Rick James

No explanation needed here. This was the two-piece that really elevated Chappelle’s Show to a new level. The combination of Murphy and Chappelle as James was magic and anyone that watched these two sketches probably still remembers most of the words to this day, 10 years later.

Making the Band

Having the actual rappers from Diddy’s Making the Band in the skit was an automatic win because you know they had been subjected to some ridiculousness during the actual filming of the reality show. Dave as Diddy is perfectly absurd and you know a skit is eternal when years later, people still know that the Top 5 rappers of all-time are Dylan, Dylan, Dylan, Dylan and Dylan.

Samuel Jackson Beer

Forget Sam Adams; try yourself a Sam Jackson. Even though it’s relatively short – it was a commercial, not a full sketch – this was amazing. “This is the way I talk! Haven’t you seen my movies?”

White People Dancing

Featuring special appearances by John Mayer and Questlove of The Roots, this is seriously stereotypical, but hilarious at the same time. The best part is Mayer smiling, but not missing a beat when a random bra gets thrown at him by the white ladies rocking out to electric guitar.

I Know Black People

It’s a close competition that also provides a lot of useful information, including definitions for terms like loosey, chickenhead, and badonkadonk. Rob the DJ may have won, but the neighbourhood barber was the best.

Law & Order: Tron Carter

Tron Carter was a recurring character – a cocaine dealer who popped up in a couple different sketches, but the best one was when he went on trial in a Law & Order episode where he found creative ways to invoke the Fifth Amendment after each question he’s asked. Fifth! One, two, three, four, FIFTH!

NEXT: Tyrone Biggums, R. Kelly, When Keeping It Real Goes Wrong, Kneehigh Park and Charlie Murphy’s True Hollywood Stories: Prince…

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E. Spencer Kyte

E. Spencer Kyte is a freelance journalist based in Abbotsford, British Columbia, where he lives with his wife and dog. In addition to his work here, he writes about sports for Complex Canada and covers the UFC for various outlets. His mom also still tells him what to do on a regular basis, even though he’s nearly 40. He tweets from @spencerkyte.

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