‘Chappelle’s Show’, 2004
No article about Dave Chappelle would be complete without those four words – they’ve been a gift and a curse for the 41-year-old comic. ‘True Hollywood Stories: Rick James’ is probably the most famous skit from ‘Chappelle’s Show’ – the Comedy Central sketch series that made his name (literally). It features cast member Charlie Murphy (brother of Eddie) describing his strange encounter with the ‘Super Freak’ singer, played by Chappelle, who constantly boasts that he’s ‘Rick James, bitch!’ When it originally aired Facebook had just been launched, the sketch went viral before that was a thing, and wherever Chappelle went came an echo of ‘Rick James, bitch!’ heckles. If you’re seeing Chappelle this week, don’t yell it out, okay?
‘For What It’s Worth’, 2004
The DC-born comic has never been one to shy away from contentious issues. Attitudes to race, drugs and sex are often big topics. In his 2004 stand-up special, ‘For What It’s Worth’, Chappelle comments on the rumours of R Kelly allegedly having sex with, and urinating on, an underage girl (he was later found not guilty) and asks America to decide, ‘How old is 15, really?’ In just a few minutes he exposes the hypocrisy and prejudice of the American media and legal system while retaining a mischievousness that’s irresistibly funny.
‘Killing Them Softly’, 2000
Chappelle’s stand-up isn’t all weighty politics. Dave can be silly, too. In ‘Killing Them Softly’, his 2000 special, he claims TV is conditioning children and launches into a stupidly funny routine about ‘Sesame Street’, insisting the show teaches kids to judge and label others (Oscar the Grouch) and features drug addicts (Cookie Monster) and pimps (The Count). ‘Don’t even tell me how to get to “Sesame Street”, that is a terrible place!’ It’s Chappelle at his most playful.
‘Chappelle’s Show’, 2004
Proper goofiness mixed with razor-sharp satire. This sketch from ‘Chappelle’s Show’s second season spoofs the sports league ‘drafting’ process to decide, once and for all, which race can claim which multiracial celebrity. Half-black, half-Thai Tiger Woods is drafted by the black representative, the Jews claim ownership over Lenny Kravitz and the Wu Tang Clan officially become Chinese. Post-Rachel Dolezal, the sketch has a whole new layer of absurdity.
‘HBO Comedy Half-Hour’, 1998
It’s familiar comedic territory, but Dave Chappelle’s take on our ‘drug-infested’ world is some of the funniest material there is on the topic. From tales of crack-addicted landlords to his one, terrifying mushroom trip, his laidback yet vivid storytelling is a joy.
‘Chappelle’s Show’, 2003
Chappelle introduces his show’s skits with a minute or so of stand-up. But this one doesn’t have much of an intro. He simply says that the sketch might get the show cancelled, and let it run. The mockumentary piece features Chappelle as Clayton Bigsby, a reclusive, blind, white-supremacist author who doesn’t realise he’s actually black. Cue Chappelle, in hillbilly get-up, spouting horribly racist comments about African Americans with liberal smatterings of the word ‘nigger’. He says it’s ‘probably the wildest thing I’ve ever done in my career.’
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