Though no one understood it then, Chappelle’s Show would become a time capsule of its creator’s most searing work on the marriage of race and Hollywood fame. Maybe more than ever funny man before him, the D.C. native used his closeness with singers, rappers and other comedians to lay bare the contradiction of being both oppressed and impressive. Somehow and always, laughing while Black.
To that point, Dave Chappelle spared no pal his biting humor, no political figure his best critique, and no punchline his hearty inner chuckle. It was less like Chappelle was a celebrity himself, more like he was their jester, free to roam among them and observe what only he could. The inside man with a story about everyone, for everyone.
So when Chappelle’s Show premiered Charlie Murphy’s True Hollywood Stories, a nostalgia piece about floating on celeb clouds with Fame Gawds like Rick James and Prince, television changed forever.
Because they were funny. In real life.
Prince was funny as hell with his pancake taunts during a pick-up game (which he reminded Chappelle of years later during a run-in). Rick James said “F*** yo couch” and was immediately your rudest friend. Dave Chappelle didn’t need the status protection that his celebrity afforded him, especially when he could make a popping roast session out of some intimate moment.
“It looked like something a figure skater would wear,” Charlie Murphy accented, shade flooding his tone, unafraid to poke fun at Prince for his risqué androgyny. But also sure to note that Prince, the epitome of cool, could be joked on just like anyone else. Between Murphy comparing The Purple One’s velvet wears to a “Zorro type” outfit, and Chappelle arresting his lids to mimic that blank Prince stare. The one with all the side-eye, and general disappointment and boredom with the mortal Earth.
But Chappelle’s impression broke through that veil so willfully, every serious Prince face he made was a new reason to laugh at this once-enigmatic musical elf.
Because Prince couldn’t be that serious and saying: “Game. Blouses.” He couldn’t be. And that crazy irony was the source of our new understanding of big-time musicians. So thank Dave for the look inside the humor of one of black music’s true icons. Who wanted to make us groove, when he could have been making us laugh just as hard.