Dave Chappelle’s 5 Most Unforgettable Characters from ‘Chappelle’s Show’

Dave Chappelle is one of the first names anyone familiar with stand-up comedy would remember. He is, for many, the best of all time.

But stand-up isn't exactly what made him the household name in comedy.

Chappelle's true launching pad to his now-stratospheric fame was his legendary skit show, Chappelle's Show, something he created with Neal Brennan.

The Comedy Central show was a genre-defining one, the like of which has never been replicated.

At the heart of the show were its characters — outrageous, absurd, and most importantly, hilarious.

And at the heart of many of those characters was Chappelle's brilliance, both in coming up with them and then bringing them to life. He portrayed around 25 characters during three seasons.

While all of them deserve their feature pieces, there were some that truly left a mark on everyone.

Those are the unforgettable ones that people keep revisiting, the ones that have left a big imprint on pop culture.

5. Lil Jon

Chappelle brought the character of Lil Jon to life on February 25, 2004.

Chappelle's Show was his to bend and break as he wished, and it always had been a hip-hop-influenced program.

So he put a bit of over-the-top spin on Lil Jon, a character who already had a larger-than-life persona in reality. The first skit was named 'A Moment in the Life of Lil Jon.'

Dave Chappelle portrays an exaggerated version of Lil Jon. (Photo: Twitter)

He introduced the skit on stage on the show, saying Lil Jon's music got him "so amped," but exaggerated the rapper's habit of saying "oh yeah" in his songs. And that was the entire premise of the sketch.

Chappelle portrayed Lil Jon dressed up in fake dreads, a cap and going through airport checking like any regular person. But, while communicating with the teller, the only words he uses are "YEAH!", "WHAT?" and "OKAY??"

He also calms down in-between his screaming, replying calmly in an accented voice.

But the loud single-word responses, which highlight the real Lil Jon's personality, are what makes the character funny and memorable.

In another skit, Lil Jon is giving an interview, where again, his only responses are "YEAH!", "WHAT?", and "OKAY??" with a few sentences of calmness towards the end of the conversation.

These were two of the many times Chappelle played Lil Jon, and the portrayal was so hilarious the skits turned into fond memories for comedy and hip-hop fans alike.

Even the show's producer loved it and tried copying Chappelle's version of Lil Jon.

4. Prince

Prince has long been one of Chappelle's Show fans' most-loved characters. And it's not just the fans who love the portrayal — Prince himself was a big fan.

The comedian's skit, 'Charlie Murphy's True Hollywood Stories — Prince,' first aired on February 18, 2004. And the story in the routine was based on a real event. 

He wanted Prince to portray himself in the skit. But after the legendary singer refused, he decided to do it himself. And what a great job he did.

In this one, Prince, Charlie Murphy, and his crew play a game of basketball.

Chappelle's Prince was dressed in a purple outfit with a blouse and wig; only he was much taller than the singer.

Donnell Rawlings, who portrayed the iconic Ashy Larry, another one of Chappelle's brilliant brainchildren, testified Prince was a huge fan of Chappelle's portrayal of him.

"He thought it was hilarious," Rawlings told Hollywood Reporter in 2016. "And I think [Chappelle and Prince] really built a friendship after that sketch."

Prince used Dave Chappelle's image, portraying him on 'Chappelle's Show,' as the cover for his 2013 single 'Breakfast Can Wait.' (Photo: Twitter)

Chappelle's Prince and the real person looked so similar that people mistook one for the other.

Prince even used an image of Chappelle dressed up as him as the cover for his 2013 single 'Breakfast Can Wait.'

3. Clayton Bigsby

Clayton Bigsby is as self-unaware a character as anyone can ever find on TV. Considered one of the best characters Chappelle has ever come up with, Bigsby is one hilarious fictional being.

Dave Chappelle portrays Clayton Bigsby, a black, blind white supremacist. (Photo: Twitter)

He is a blind, black, white supremacist. But the thing he initially does not realize is that he is black because he's blind and nobody told him.

With a strong hatred for a race he does not realize he belongs to, he becomes the leading voice of the white supremacist movement in America.

He achieves this without a single public appearance. He never leaves his house without a white hood until his appearance on Frontline.

The public debut changes his life forever. He realizes he is African-American, at which point, he ends his 19-year marriage.

His reason? He did not want to be with a woman who dated outside her race; only he used more racist words to convey that.

The character's profoundly ironic existence and the generous use of the n-word made the skit more hilarious than any description could ever do justice.

And as the skit that started Chappelle's show, it set the bar really high for Chappelle.

2. Tyrone Biggums

If Bigsby was the opening episode, Biggums was the second, and boy did Chappelle clear the high bar he set for himself.

Chappelle's crackhead man-child character, Tyrone Biggums, was a humorous take on addiction, coming at a time when the crack epidemic was still a big topic.

A homeless person, Biggums is a crack cocaine addict, quickly recognized by his white, blistered lips and constant scratching.

His other trademark character features are eating peanut butter and crack sandwiches and saying, "I smoke rocks!"

Many of his dialogues, such as "Y'all got anymore of..." and a particular line that shows his extreme willingness to perform oral sex on a man for the white powder have become a mainstay in the meme culture.

Dave Chappelle portrays the always-itchy Tyrone Biggums. (Photo: Twitter)

For Biggums, fear was never a factor when it came to getting some crack, as evident in his appearance on a spoof Fear Factor episode alongside Joe Rogan.

And neither was a lack of wide-enough passageways, as he once flushed himself down a toilet to escape rehabilitation.

With his recurring appearances within iconic sketches, Biggums became one of the most unforgettable characters Chappelle has ever written.

1. Rick James

If Biggums became legendary memes, Chappelle's Rick James became a phenomenon that transcended comedy itself.

Rick James isn't exactly a character but an exaggeration of Rick James, an American singer-songwriter's personality.

James, like Prince, appeared on 'Charlie Murphy's True Hollywood Stories,' for the first time on February 11, 2004.

Chappelle took James's character and elevated it to include exaggerated mannerisms and similar but REAL stories, narrated by Eddie Murphy's brother Charlie Murphy.

Things like James slapping Murphy, referring to him as 'Darkness,' and the real James's interviews trying to justify his past behaviors all made Chappelle's portrayal amazing.

But the main thing people remember about James is his famous catchphrase — "I'm Rick James, [expletive]!"

Dave Chappelle portrays an exaggerated version of Rick James. (Photo: Twitter)

The line became so famous that it turned into something destructive.

There's one incident where, in 2005, a Mississippi city council candidate named Rick James, with no connection to James or Chappelle's portrayal of him, had a difficult time trying to cope with the infamy of the dialogue.

His campaign slogan, "Vote Rick James," was often defamed by fans of the sketch, changing it to "Vote Rick James [expletive]!"

James's skit was too big for its own good and became the ultimate reason Chappelle stopped doing the show.

While performing stand-up in 2004, the audience started chanting the dialogue, making Chappelle leave the stage mid-set.

Chappelle said he was getting frustrated with the success of the show and the impact it was having on his life.

So valuing his stand-up career more than the sketch show, he went on a hiatus in April 2005, ending once and for all what is probably the most brilliant sketch show to ever air on TV.

Nevertheless, for both good and bad reasons, James became Chappelle's most unforgettable portrayal, if not a character.

There are a few other brilliant characters, like Black Bush, Silky Johnson, and Leonard Washington, which did not make this list but still deserve honorable mentions.