Looking Back At Charlie Murphy’s Greatest ‘Chappelle’s Show’ Moments

The 2010s have given us sporadic Dave Chappelle offerings. We saw him make the late night rounds on Letterman and Kimmel, in 2014 and crash the Today Show, and perform a block of concerts at Radio City Music Hall for the luckiest people on the planet. Then of course, he gifted us all out of the blue with not one, but two new stand-up specials on Netflix this year. A thousand thanks for that, Dave.

The Chappelle’s Show‘s influence on comedy and pop culture can’t be underestimated, and two of its most well-known, most quoted and most GIF-able sketches can be credited to cast member Charlie Murphy, who sadly died on Tuesday at the age of 57.

The older brother of Eddie Murphy had an almost infinite number of stories to pull from about witnessing the bizarreness that is being a celebrity. In honor of his memory and the work he did on Chappelle’s Show, we’re re-running this 2014 look back at his finest moments on the show. Plus, one Charlie Murphy True Hollywood Story that unfortunately never became a sketch.

“Mad Real World”

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“Mad Real World” was one of Charlie’s standout sketches from the first season of Chappelle’s Show. The entire fish out of water premise is funny enough, but Charlie’s character Tyree was nothing short of a roommate nightmare and one of the sketches best characters.

“Charlie Murphy’s True Hollywood Stories: Prince”

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Charlie Murphy’s story about his Prince encounter was his follow-up to meeting Rick James, and while it lacked the face slapping, it was just as over the top ridiculous. From Prince making the losing team pancakes to Dave Chappelle levitating after his dunk, everything about the sketch is silly in the best way possible. If I had to give it one criticism, it’s only that we didn’t get to hear Prince’s take on the game like we did with Rick James.

“Player Haters Ball”

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“Player Haters Ball” is a perfect example of a show taking pop culture slang and building a hilariously original idea around it. The sketch would have been great with just Donnell Rawlings and Charlie Murphy, but the addition of Patrice O’Neal and Ice-T elevated it to a new level. “Hate, hate, hate, hate.”

“Kneehigh Park”

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Other sketch shows had parodied Sesame Street before, but amazingly never thought to play on the obvious fact that Oscar the Grouch is miserable for a reason. The idea behind Kneehigh Park’s version of Oscar came from one of Chappelle’s Killing Them Softly bits, and Charlie Murphy’s gritty voiceover of the puppet drove the idea home.

“Charlie Murphy’s True Hollywood Stories: Rick James”

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Not only was this Charlie Murphy’s greatest moment on the show, but it’s arguably the show’s most well-known sketch. One of the things that made the sketch so great was that it wasn’t just your standard sketch with actors portraying these characters, but included intersecting clips of Charlie telling the story and Rick James remembering — or trying to remember — how the events played out. Charlie revealed on Artie Lange’s podcast that the idea for the sketch came about on a lunch break when he was casually telling the story of how he met Rick James, and it was Chappelle who instantly recognized it as a great sketch idea.

I can only assume this photo of Charlie and Rick James hanging out is pre-five fingers meeting the face.

Charlie Murphy, Redd Foxx, and the black tooth.

This never became a Chappelle’s Show sketch, but Charlie’s story of working with his brother and comedy legends Red Foxx and Richard Pryor on 1989’s Harlem Nights is ripe for the “True Hollywood Stories” treatment. Charlie told the story on Snoop’s GGN YouTube show that he had invited his friend Woody down to the set one day. Woody had a dead tooth that became the focal point of Redd Foxx’s attention for an hour of jokes.

“I had a friend named Woody and from the time Woody was maybe 11 until he was deep into his 20s he had one black tooth. Never got it fixed. You would think that he would get enough money to get that fixed, 10, 12 years in and his tooth was still black. He met Redd Foxx and Redd Foxx did an hour of stand-up on his black tooth. The very next day Woody had his tooth fixed. Redd Foxx rehabilitated that man’s smile with jokes.”

This is an updated version of a post that originally ran on July 11, 2014.