Charlie Murphy True Hollywood Stories – Rick James
Four words that changed the face of comedy forever. “I’m Rick James b*tch!”
Clayton Bigsby — the blind, black white supremacist
A blind black kid was adopted by a white family and becomes a popular KKK leader. Self-hating humor at its finest.
‘Making the Band’
Chappelle’s Puffy and Dylan impersonations are amazing as the hip-hop mogul puts Da Band members through the ringer — sending them on wild goose chases for sugar cookies and Cambodian breast milk.
The ‘Playa Hater’s Ball’
This sketch shows not only how funny Chappelle is, but showcases his supporting cast as well. Check out how Donnell Rawlings, Charlie Murphy, and the late Patrice O’Neal go at it with Chappelle to see who the ultimate hater is.
Wrap It Up Box
Whether it’s a sentencing at a trial, a boring acceptance speech or a truly unsatisfying sexual encounter, the Wrap It Up Box shuts down anyone who can’t take a hint.
Charlie Murphy True Hollywood Stories – Prince
According to Charlie Murphy, The Purple One’s basketball skills are second to none. Game. Blouses.
Wholesome Wayne Brady channels his inner Alonzo Harris from Training Day, as he takes Chappelle for a late night ride in his SUV and shows how ‘funny’ he really is.
Before Obama there was ‘Black Bush’. Black Bush and his administration may have been inept at saving the world, but there was plenty of “yellow cake” to go around.
‘Mad Real World’
Since its inception, MTV’s Real World series has sprinkled one, maybe two black people in a cast of seven. Well Chappelle flipped the script and dropped the Caucasian Chad in a house full of stereotypical blacks. Awkward comedy ensues.
‘When Keeping It Real Goes Wrong’
This series of skits focused on what happens when a person decides to not take the high road when they felt they’ve been slighted. The two best featured a woman who is obsessed with people “playing on her phone” and Chappelle as an employee pissed at a white co-worker’s offer of a high five.
In the early 2000s, when reality shows were all the rage, Fear Factor had contestants jumping out of planes, sliding down buildings etc. When you bring the crackhead Tyrone Biggums on to compete, he’ll do anything, and we mean anything to win.
World Series of Dice
Parodying ESPN’s coverage on smaller sports, Chappelle held an underground dice tournament live from the Marcy projects. In this skit, the world was introduced to the one-and-only Ashy Larry.
Samuel L. Jackson Beer
Chappelle portraying the foul-mouthed Oscar nominee as a pitchman for any product is a great idea. Replacing Sam Adams for Sam Jackson is an incredible idea that Chappelle executed flawlessly.
The Niggar Family
Imagine if your last name was the n-word (or sounded similar to it). Now imagine that being your last name and you’re white. This is how this skit begins.
R. Kelly/’Pee on You’ parody
Even R.Kelly wasn’t safe when Chappelle made a music video in reference to Kel’s fondness for urinating on young girls.
Have you ever hesitated to eat fried chicken in front of mixed company? Listen to your own personal racial fairy next you feel like you should pass on that yard bird the next time a white person is present.
Law & Order parody
When drug dealer Tron gets arrested for selling cocaine, he pleads the Fiiifff to all charges in this uproarious re-imagining of the hit NBC crime series.
Combine the excitement of the NFL draft with the cultural pride that all races have and the results is the Chinese drafting the Wu-Tang Clan, black people (represented by a costumed Mos Def, pictured above) drafting Tiger Woods, and white people trading for Colin Powell.
I Know Black People
Another game show skit where a professor, your local dope boy, an NYC officer and local barber (among others) compete to see who knows black people the best.
While Tupac Shakur did indeed die in 1996, he continued to have a very successful rap career. In this skit, Pac raps about former President W. Bush and videogame Grand Theft Auto: San Andreas which are two subjects that were clearly after his time.
- of 20
Today marks beloved black comedian Dave Chappelle‘s 39th birthday. Sadly. for the last few years Chapelle has remained largely out of the spotlight, with the exception of a few stand up appearances, which have received mixed reviews. Still, his greatest work, Chappelle’s Show, stands the test of time.
We here at theGrio are always quoting his best sketches ad nauseam and to mark Chappelle’s big day we’re picking our 20 favorite bits from his classic show.
Take a look a look at our slideshow and see if your favorite funny moment made the cut.