In the mid-2000s, there was nothing bigger than Chappelle's Show. It was a cultural tour de force that turned the television world upside down, and recreated what people thought sketch comedy could be. The very first episode was a statement of intent; Chappelle's performance as a black white supremacist, Clayton Bigsby, showed no topic would be off limits.
But there is no Chappelle's Show without Charlie Murphy. There were more frequent collaborators on the show, but no one aside from the show's namesake made a bigger impact than Murphy did. He was part of several of the show's most popular sketches, which have allowed it to live on despite being off the air since 2006. His impact has been felt on several levels, from catch-phrases that live on to this day to the introduction of phrases that can be used to sum up everyday occurrences people go through.
It's hard to pin down's Murphy's career and influence to just a few bits or sketches, but these are the moments that will live on long beyond his passing.
The Rick James Sketch
Murphy will forever be associated with his retelling of Rick James' cocaine-induced mania in the 1980s, and it is arguably the peak of the show. After Chappelle sets the sketch up to the audience by talking up his co-worker's storytelling, Murphy launches into a story that features a wigged Chappelle standing in for James, and the audience watches him antagonize the Murphy brothers to the tune of destroying Eddie Murphy's couch and slapping Charlie Murphy across the face.
Chappelle himself has alluded to the singular popularity of the sketch in stand-up performances since it released. In his stand-up special, For What It's Worth, he tells the crowd he can't even go to Disney World without being accosted by passersby (including Mickey Mouse!) with the episode's signature line: "I'm Rick James, bitch!"
Murphy's retelling of the story is an all-time classic, and small details from the story will help him live on even as Chappelle's Show begins to fade from popular culture. One moment in particular, where Murphy describes James as a "habitual line-stepper," is a perfect summation of the friend we all have who doesn't know the difference between having a good time and taking things too far:
The genius in this sketch is in that moment. It's a story about a group of celebrities who are living lavishly in ways most can't dream of, but they're experiencing relatable problems friends deal with when their wild card buddy gets out of control. Murphy makes Rick James feel like the kid you knew in college who couldn't handle their liquor, and it's an extraordinary feat.
Buc Nasty, The Playa Hater Extraordinaire
If the strength of the Rick James sketch was rooted in real life, "Playa Haters' Ball" succeeds for the exact opposite reason. A group of swashbuckling pimps assembling in a conference room like they're holding an annual finance seminar is a premise so absurd there is almost no margin for error. Yet thanks to a talent like Murphy, Chappelle's Show pulled it off.
The mockumentary begins with a series of interviews with participants in the Playa Haters Ball, as they explain the art form of being a hater and why they're a cut above the competition. But the first one-liner of the sketch was held for nearly two minutes, when Chappelle's Silky Johnston character enters the building with a walking cane in his hand and a mink coat on his back.
Murphy is unfazed. "Man, you oughta take that cane and beat whoever made that suit to death."
It sets the stage for another five minutes of Murphy, Chappelle, Rawlings, and Patrice O'Neal trading barbs back-and-forth in an effort to one-up the next guy. Each man struggles to hold it together throughout the bombardment, but Murphy is the most outwardly affected by the jokes. You can see him visibly swaying in an attempt to save face after Chappelle says his coat is made out of O'Neal's mother's pubic hair, and after an insult is lobbed at Rosie O'Donnell in the speed round, Murphy is so beside himself he has to physically exit the semi-circle to avoid breaking character.
Murphy's joy is evident even in the outtakes for the sketch, which show him preparing to shoot with a giant smile on his face.
For as gruff as Murphy could be—his character accosts a female companion late in the sketch when she fails to clap for him—his inability to hold back emotions of any kind is what made him such a beloved comedian. Everything he did was outsized and expressive, which allowed him to inject life into even the smallest moments. For a sketch like "Playa Haters' Ball", that worked like a dream.
Later on in the series, Chappelle showed off a number of failed premises that never became full sketches. One of those showed off the Playa Haters traveling back through time just to insult (and shoot) former slave masters, and it really deserved to be turned into a fully-developed episode.
Tyree, The Mad Real World
In this over-the-top lampooning of MTV'sReal World series, Chappelle and an extended cast of characters poked fun at the fact that the show was often dominated by white people, with the lone minority in the house being painted as the wild or crazy one. Chappelle's version of the "Mad Real World" features an unsuspecting guy realizing he's the lone white person in his new setting, and things quickly go off the rails when he doesn't fit in.
The first sign of trouble for young Chad is when he stares down Murphy's character, Tyree, who gleefully greets the audience with an assertion about his stint in jail. Making sure his roommate knows what time it is, Tyree quickly establishes the bathroom habits Chad should follow, has sex with Chad's girlfriend, and yells at Chad when he breaks up a back-alley dice game between other roommates in the house.
"Mad Real World" was a brilliant flip of the paradigm that plagues most reality shows. Murphy's dad-stabbing, cigar-smoking character was a key ingredient in making it as great as it was.
Prince, Star Basketball Player
After the success of the Rick James escapade, Murphy returned to share another one of "Charlie Murphy's True Hollywood Stories." It featured another mega-star from the 80's, but the legend of Prince grew after Murphy was done telling this one.
Describing the pop/rock star with comparisons to Iverson, Murphy's storytelling is accompanied by a dramatic reenactment of a pickup basketball game between Murphy's crew and Prince's, with the Revolution stunting all over Murphy's pals despite being decked out in the same clothes they wore to the club. Unlike most stories about games between friends, Murphy does not try to paper over the beatdown Prince laid on him, and says it was a "landslide victory" in favor of his opponent.
Chappelle turns in a haunting performance as Prince, floating down from the rim after dunking like some sort of purple-clad ghost, but the best moment in the episode once again goes to Murphy. As his story is winding down, he talks to his interviewer off-camera and is asked what happened after the basketball game is over. With every ounce of seriousness he can muster, Murphy looks into the camera and says simply, "He took us inside the house and made us pancakes."
Thanks to Murphy, we all know Prince is gracious in defeat.