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Higher Learning. A publication from Medium for the interested man.

Dave Chappelle

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The late great comedian was underrated, unapologetically Black, and the Richard Pryor whisperer

Photo: Getty Images

Dave Chappelle’s childhood idol worship of Richard Pryor should come as no surprise. Of course, Chappelle was obsessed with the man who he and much of the world crowned the king of comedy. He remembers being entranced by a particular skit from the first season of Saturday Night Live. Pryor played a job applicant who finds himself in a heated word-association game with a prospective employer (played by Chevy Chase). Chase’s character begins throwing racial slurs; Pryor’s returns fire. For young Chappelle, witnessing a Black man go toe-to-toe with a White man was revolutionary television. Chappelle says it was at…


Just Rankin’ Sh!t

The comic’s big-screen turns that paved the way for ‘Chappelle’s Show’

Photo illustration; image source: Tim Mosenfelder/Getty Images

5. “Robin Hood: Men in Tights”

In Chappelle’s coming-out party, he plays Robin Hood’s sidekick — who just so happens to rock Reebok Pumps and drop a Malcolm X impression, just for the hell of it. Not bad for a 19-year-old.

4. “Undercover Brother”

Legend has it that Chappelle ad-libbed most of his lines as Conspiracy Brother while shooting this one. Huge, if true, because every quip he drops in Eddie Griffin’s magnum opus lands real-life LOLs. (Whatever happened to Eddie Griffin, anyway?)

3. “Blue Streak”

Come for two legends — Chappelle and Martin — tossing each other alley-oops like Bron and D. Wade in this heist flick turned cop comedy. Stay…


In “America Taught Dave Chappelle That Millionaires Can Sharecrop Too,” Bonsu Thompson unpacks Chappelle’s most recent standup routine, in which the comic related his struggles with Comedy Central licensing Chappelle’s Show for streaming without giving him a cut of the revenue. “Whether the gap is money, notoriety, physical strength or civil rights,” Thompson writes, “in the United States especially, the lesser someone has the greater chance that they become prey.”


On the day of Joe Biden and Kamala Harris’ win, the comic delivered a ‘Saturday Night Live’ monologue that was cerebral, sharp, and timely

Photo: NBC

Dave Chappelle’s 16-minute Saturday Night Live monologue was the complete Chappelle experience. It’s honestly an intimidating task to even try to absorb and put together cogent thoughts about something so layered and massive.

So, let’s start with the Klan joke.

Chappelle opened with jokes about his own career, including stories about his White neighbors and his royalty structure. (Somehow he’s not earning anything from HBO and Netflix now syndicating Chappelle’s Show?!)

Centering himself and his fame has been a feature in Chappelle’s stand-ups for the past decade — with mixed results. At the beginning of the monologue, he eased us…

LEVEL

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