Let’s Look Back At Charlie Murphy’s Greatest ‘Chappelle’s Show’ Moments

By: 07.11.14  •  29 Comments

Comedy Central

So far, 2014 has given us more Dave Chappelle than any other year this decade. We’ve seen Dave make the late night rounds on Letterman and Kimmel, crash the Today Show, and perform a block of concerts at Radio City Music Hall for the luckiest people on the planet. I’ve seen several people wearing the shows’ concert shirts and it takes every fiber of my being to keep from lashing out at them in a jealous rage.

It’s been a decade since Chappelle walked away from the show and the biggest paycheck in the history of Comedy Central. The 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. The older brother of Eddie Murphy has an almost infinite number of stories to pull from about witnessing the bizarreness that is being a celebrity. If you’ve never watched his video about working as Eddie’s bodyguard in the 1980s, take a brief break from work to do so — just make sure you plug those headphones in (very NSFW).

Charlie Murphy is celebrating his 55th birthday today, and in honor of his work on Chappelle’s Show, we’re looking back at his finest moments since it finished its all too brief 28 episode run. 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 of a doughy white kid living in a house with African American roommates who don’t want him around is funny enough, but Charlie’s thug character Tyree was nothing short of a roommate nightmare and one of the sketches best characters.

“Charlie Murphy’s True Hollywood Stories: Prince”

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”

“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”

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.

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