Dave Chappelle’s Comedy Central show, Chappelle’s Show, may not have been around long but it certainly made its mark landing on Entertainment Weekly’s New TV Classics list and being hailed on TV Guide’s Top 100 Shows ranking. An American sketch comedy show created by Chappelle and Neal Brennan, the show tackled sexuality, drug use, prostitution, gun violence, the entertainment industry and more, and was notorious for its antagonistic approach and wildly inappropriate—yet hilarious—characters and impersonations.
The show quickly became one of the most quotable shows of its time thanks in part to Chappelle’s portrayals of people like Lil Jon and Prince (among others). Airing between 2003-2006, Chappelle’s Show capped its episodes with a musical performance by rap and soul artists, and provided extremely sharp and slightly sinister takes on the racial and social issues that continue to plague our country. He was always joined by a mass of huge guest stars that included Kanye West, Talib Kweli, Ludacris, Susan Sarandon, Ron Jeremy, Joe Rogan, and many more.
With only 28 episodes in total, revisiting the show’s glory days isn’t a huge commitment. Here’s how to watch Chappelle’s Show streaming online.
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How to Watch Chappelle’s Show Online & Stream the Complete Series
Chappelle’s Show remains absent from the likes of Hulu, Amazon Prime Video and Netflix in the United States, but every episode can be watched on Comedy Central’s website.
You’ll need to log-in to a cable provider to watch this way, but if you don’t have cable you can sign up for a free trial of DirecTV Now and then use those credentials to sign in and watch Chappelle’s Show on the Comedy Central digital platforms.
How Many Chappelle’s Show Seasons Are There?
Chapelle’s Show ran for only three seasons despite being one of the top comedies, sketch or otherwise, of its time. After producing just three episodes of its third season, Chappelle walked away from a reported $50 million deal from Comedy Central, a network that was yearning for more of Chappelle’s cultural comedy…and willing to pay a lot of money for it.
Chappelle’s Show Season 1
12 Episodes | January 2003 – April 2003
Back when TV shows on DVD was a thing, the very first season of Chappelle’s Show sold more than two million copies making it one of the most successful seasons of television produced. A pure moneymaker for its network, Comedy Central, Chapelle’s Show was one of the most talked about shows before the social media boom, becoming an instant classic and prime fodder for watercooler convos. Some of the season’s most memorable skits include Third World Girls Gone Wild, Pretty White Girl Sings Dave’s Thoughts, HBO Real Sex Street Interview, Wu Tang Financial, Blackzilla and Roots Outtakes. Musical guests included Killer Mike, Fat Joe, The Roots, De La Soul and many more.
Chappelle’s Show Season 2
13 Episodes | January 2004 – April 2004
Along with John Mayer and Questlove, Chappelle explored the art behind White People Dancing. Charlie Murphy’s True Hollywood Stories skits introduced Chappelle’s impersonations of Prince and Rick James, leaving the entire country screaming, “I’m Rick James, bitch!” The Wayne Brady Show showed viewers an entirely different and darker side to Brady than we’ve ever seen before (“Is Wayne Brady gonna have to choke a bitch?”). Other popular skits include When Keeping It Real Goes Wrong and A Moment in the Life of Lil Jon, which ended up becoming another obscenely popular Chappelle character.
Chappelle’s Show Season 3
3 Episodes | July 2006 – July 2006
Season 3 was deemed “The Lost Episodes” when it finally hit airwaves more than two years after its second season finished its run. Chappell waxed poetic about how he was now $55 million richer. Skits about Tupac still being alive and watching TV while having sex hit big. Lil Jon finds love, and Chappelle becomes P. Diddy appearing on MTV Cribs.
What Are the Best Chappelle’s Show Episodes?
Come for the outrageous characters, stay for the dynamite musical performances. Here’s a list of the best Chappelle’s Show episodes:
Season 1, Episode 2
In the series’ second episode, Chappelle introduces Tyrone Bigguns, a crackhead who visits an elementary school to keep kids off drugs. Bigguns is known for his white, blistered lips, constant scratching and love for peanut butter and crack sandwiches. The character would continue to appear sporadically throughout the series and it didn’t take long for him to become a fan-favorite. This episode also featured sketches called “Pretty White Girl Sings Dave’s Thoughts” and “Wrap It Up.”
Season 1, Episode 6
Chappelle spoofs Girls Gone Wild swapping hot girls for women from the third world. In one of the best skits of the series, Chappelle takes on “The Real World” when one white person moves into a house full of black roommates. (People “stop being polite and start getting real,” obviously.)
Season 1, Episode 8
A mock-Frontline episode investigates racism in some of Hollywood’s biggest (animal) stars like Flipper, Mr. Ed and Rin Tin Tin. Dave imagines the reverse of the movie What Women Want by removing two tiny letters from its title. Turns out “What Men Want” isn’t that hard to figure out.
Season 2, Episode 1
Samuel L. Jackson markets his new beer in a spoof of Samuel Adams. In “The Racial Draft,” the comedian imagines what would happen if stars were drafted into certain races. Tiger Woods becomes “all black” while the Wu Tang Clan is drafted by Asians.
Season 2, Episode 7
The second showing of Chappelle as Lil’ Jon finds Jon prepping for an interview with a Barbara Walters-esque journalist. A mock marijuana commercial parodies anti-drug spots that aired earlier that year.
Who Are the Actors in the Chappelle’s Show Cast?
Chappelle was clearly the star (it’s not just a clever name), but he had a few key figures in tow to help bring his Show come to life.
Dave Chappelle as Himself, Prince, Lil Jon, Rick James and more
The stand up comedian and Half Baked star took center stage on screen, but he was also an executive producer and a writer. Chappelle also appeared in Robin Hood: Men in Tights and 200 Cigarettes. He’ll also be seen on the big screen in this year’s upcoming A Star Is Born remake.
Donnell Rawlings as the announcer and various characters
Rawlings played many characters on Chappelle’s Show, but was mostly known for his announcing duties and for his character Ashy Larry. Rawlings is also well known for his stint on The Wire as Damien Lavelle ‘Day-Day’ Price.
Charlie Murphy as various characters
Charlie Murphy’s True Hollywood Stories was one of the most famous Chapelle’s Show skits where Murphy (who also wrote the sketches) regales viewers with his encounters with celebrities in the ’80s. The most popular version introduced Rick James into the show. The late Murphy also starred in The Boondocks and Are We There Yet? along with the Starz series Power.
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Who Are the Top Guest Stars on Chappelle’s Show?
Chappelle’s Show had an endless amount guest stars, so many that it’s nearly impossible to name them all. In terms of musical guests, Chappelle had DMX, Wyclef Jean, Cee-Lo Green, Mos Def, Busta Rhymes, Snoop Dogg, Big Boi, Common, Kanye, Erykah Badu, De La Soul and more. The musical performances helped break up the show’s bit-sketch-bit-sketch format and as evidenced by the list, Chappelle booked some of the biggest names in hip-hop at the time.
Performances aside, many of Chappelle’s guests would star in sketches with him including RZA, GZA, Method man, Redman, Ice-T, Arsenio Hall, Wayne Brady (who was the only guest to appear on stage), Eddie Griffin, Q-Tip, Michael Rapaport, Jim Breuer, Bill Burr, Carson Daly, Guillermo Diaz and more. Most episodes of Chappelle’s Show would have a famous face surprising viewers, many of whom starred in the show against type like the now classic Brady sketch.
Who Are the Writers & Creators Behind Chappelle’s Show?
Dave Chappelle: Chappelle’s Show Co-creator, Executive Producer and Writer
Chappelle Show is modeled after Chappelle’s stand up comedy which he performs in between each sketch. Before he landed his Comedy Central gig, Chappelle voiced a cockroach in Joe’s Apartment and appeared in Robin Hood: Men in Tights, Half Baked, The Larry Sanders Show, Blue Streak, The Nutty Professor and more. He can currently be seen performing stand up with his new Netflix specials.
Neal Brennan: Chappelle’s Show Co-creator, Executive Producer, Director and Writer
Brennan helped Chappelle create the show and also lent his talents to writing, producing and directing the show. He got his start on shows like Singled Out, All That and Kenan & Kel. After Chappelle’s Show, he moved on to shows like The Daily Show, Inside Amy Schumer and Funny or Die Presents…
Rusty Cundieff: Chappelle’s Show Director
Cundieff is best known for his 1995 film Tales from the Hood. He’s also directed installments of shows like Chocolate News and The Wanda Sykes Show, and his Tales from the Hood sequel is set to release later this year.
Where Chappelle’s Show Ranks in the Television Pantheon
A 2004 MTV headline said it all calling Chappelle “the reason grandmas know who Lil Jon is.” Chappelle’s Show may have come and gone at break-neck speed, but his culturally relevant comedy had a widespread reach that had the whole country talking. Chappelle’s sketches about politics, drugs and race never failed to deliver, shocking the system with jaw-dropping moments that always resulted in explosive laughter. As The AV Club notes, Chappelle’s comedy was akin to Richard Pryor or George Carlin, two comedians who deftly understood that context means everything in the world of comedy. Chappelle followed suit, becoming one of the biggest button-pushing comedians of his time, crossing the line time and time again to various, but always expertly executed effects.
If rabble-rousing jokes about drugs and sex offend or if racially-charged, tongue in cheek caricatures make you squirm, this may be a Show to skip. That said, if sketch comedy, Pryor or Carlin are up your alley and you didn’t catch Chappelle’s Show during its prime, this will be one irresistible binge you won’t regret.