Top 10 Dave Chappelle Moments

#10: Where’s JA?!
“Dave Chappelle: For What It’s Worth” (2004)

Celebrity culture is ubiquitous and has been for decades now. But what really rankled Dave to hilarious effect was the tendency for news organizations to ask famous people to weigh in on heavy topics waaaay out of their depth. So in this short bit, Dave admonishes the press for inflating the already large ego of celebrities. To illustrate his point, he chose rapper Ja Rule, interviewed on MTV about the September 11th terrorist attacks. Like much of Chappelle’s standup, this jab at pop culture found a new life of its own on the Internet.

#9: Conspiracy Brother
“Undercover Brother” (2002)

In the blaxploitation spoof film “Undercover Brother,” Dave plays a conspiracy-driven agent named, you guessed it, Conspiracy Brother. Tracking down appropriations of black culture is his specialty, and he spends much of his efforts making sure all the other characters know all the conspiracies that he can make them aware of. Conspiracy Brother is a part of the B.R.O.T.H.E.R.H.O.O.D., a secret agency that puts its efforts to taking down the agenda of “The Man.” Though he rants and raves a lot in this movie, it wouldn’t be a Chappelle character if there wasn’t some weed involved.

#8: A Moment in the Life of Lil Jon
“Chappelle’s Show” (2003-06)

The early 2000s saw the rise of crunk music, and its leader went by the name of Lil Jon. In addition to deep, thumping, booty-shaking rhythms, Lil Jon is known for his full-throated strange utterances, like “YEAAAH” and “OKAYYY" throughout his songs. This got taken to a new level when Dave spoofed Lil Jon in this skit on the seminal “Chappelle’s Show”. Besides becoming one of the most popular of Dave’s skits, it also shot Lil Jon to even greater heights of fame. He still claims that he can’t walk down the street without some fan running up and screaming “YEEAAHH!” right in his face.

#7: Revealing Interview
“The Oprah Winfrey Show” (1986-2011)

What would you do if you got offered tens of millions of dollars to continue a super popular sketch comedy show? Well, if you’re Dave Chappelle, you quit, leave for Africa, and spark rumors that you have literally gone crazy. By the time he made it onto Oprah’s famous couch in 2006, fans were on edge to hear if they would ever see their beloved “Chappelle’s Show” again and find out the truth about all the seemingly strange behavior. The queen of daytime talk was the only person that he would interview with at the time, and he spent the hour walking through the highs and lows that got him to a point of no return.

#6: Return to Form
“Deep in the Heart of Texas” & “The Age of Spin” (2017)

After some time away from TV, Dave Chappelle culminated his return to fame with a vengeance in 2017, with two stand-up comedy specials released by Netflix. They, of course, garnered a hot buzz before their release, and Netflix has stated that the specials became the most viewed programs on the streaming service. . . ever. Dave’s ease with the audience and effortless storytelling are reminiscent of the glory of “Chappelle’s Show” monologues. But Netflix wasn’t the only winner, Dave reportedly took home $60 million. YEAAAHHHH!

#5: Thurgood Jenkins / Sir Smoke-A-Lot
“Half Baked” (1998)

This stoner cult classic, which he also co-wrote, was one of Dave’s first starring roles. The 1998 film brought together Chappelle and writer/comedian Neal Brennan, who would together go on to co-create “Chappelle’s Show”. The film is no stranger to controversy, with the opening scene almost yanked by the studio because it showed kids smoking marijuana. Another great reason to love this movie are all the cameo appearances from other comics like Tracy Morgan, Janeane Garofalo, Jon Stewart, and Bob Saget. Meanwhile, Chappelle had a chance to show off his acting chops, both as protagonist Thurgood Jenkins and Sir Smoke-A-Lot.

#4: The Niggar family
“Chappelle’s Show” (2003-06)

This famous skit is a spoof of a 1960’s Andy Griffith-style sitcom that stars a family with an unfortunate last name. Wrapped in this uncomfortable sequence is the social question of the use of the n-word, and the effect that it would have if it were just another name. For some viewers, it raised questions about racial versus racist humor; and it certainly pushed the limit on what you could get away with on television. For others, it was a damn funny skit that proved that we were all taking things a bit too seriously.

#3: Men and Women
“Dave Chappelle: Killin’ Them Softly” (2000)

This bit comes from Dave’s “Killin’ Them Softly” special, a fan favorite performed at the Lincoln Theater in Washington D.C in 2000. This standup set is seen as a turning point in Dave’s career, pointing him towards superstardom. Although Dave is known for his racial humor, this skit is a departure, instead focusing on the craziness between men and women and the things people go through to have relationships. This was another look at cool, calm and collected Dave, on stage and easily working an audience.

#2: Election Night Skit
“Saturday Night Live” (1975-)

Election night 2016 was quite the emotional rollercoaster in the US. At a time when the country was riven by partisanship and anger, Dave was one of the first to get people to laugh at an intense situation. This election night skit highlights the surprise and dismay of Hillary supporters who weren’t anticipating Donald Trump’s win. As the night goes on and more and more states are called for Trump, and the election night gathering turns from happiness, to disbelief, to depression. Bonus: surprise guest Chris Rock.

Before we reveal our number one pick, here are some honorable mentions.

- Party Time
“Dave Chappelle’s Block Party” (2005)

- The Mad Real World
“Chappelle’s Show” (2003-06)

- Drugs

“HBO Comedy Half-Hour: Dave Chappelle” (1994-1998)

#1: Rick James
“Chappelle’s Show” (2003-06)

Yes, it’s this skit, bitch! Chappelle’s hilarious outsized turn as the couch-disrespecting funk legend Rick James birthed catchphrases and memes galore. The skit, part of castmate Charlie Murphy’s True Hollywood Stories segment, also included the real Rick James bustin’ out his classic line (pun intended) about drug use. The quotability of the skit made it prime shareable and viral content for the burgeoning Internet hype machine. And while Rick James passed in 2004, and Charlie Murphy in 2017, but this bit of peak Chappelle remains forever alive.