Believe it or not, but it's been 12 years since the public was privy to a full season of Dave Chappelle's groundbreaking sketch comedy show, Chappelle's Show, which saw him musing on everything from race relations in the United States to the state of hip-hop. A combination of wicked criticisms and meta humor - as well as Chappelle's ability to step in the shoes of seemingly anyone - we truly didn't know how good we had it until it was abruptly stripped from our lives. Chappelle's show left one of the biggest "what if" scenarios in comedy, thanks to his disappearance soon after a falling out with both his partner, Neal Brennan, and Comedy Central.
Despite Chappelle's reemergence into the limelight thanks to a series of performances at Radio City Music Hall in New York City in 2014, his scripted fare always served as a welcome compliment to his standup material. If his on-stage performances were gasoline, Chappelle's Show was the ensuing fire after he had struck a match.
The months of March and April were always important periods for the first two seasons of Chappelle's Show - with 13 of the 25 "official" episodes airing during that time. Whereas most of the United States was emerging from the winter doldrums, Chappelle would offer up a few more visual treats and music performances before he himself went into hibernation.
If someone ever needed a Dave Chappelle "starter kit," look no further than these legendary Chappelle's Show sketches.
Frontline: Clayton Bigsby
Air date: January 22, 2003
When Dave Chappelle introduced the clip for "Frontline: Clayton Bigsby," he said, "I still haven't been cancelled yet, but I'm working on it. And I think this next piece might do it. This is probably the wildest thing I've ever done in my career and I showed it to a black friend of mine, and he looked at me like I had set black people back with a comedy sketch. Sorry..."
Throughout the show's run, Chappelle was unafraid to tackle larger issues that, to this day, continue to plague the USA. But because the lens was often ridiculous, the criticisms never felt preachy.
Tyrone Biggums' Classroom Visit
Air date: January 29, 2003
Tyrone Biggums proved to be one the longest-running recurring characters on Chappelle's Show, whose propensity for all things "drugs" made him the perfect point of entry into any situation. Thus, when placed inside a school to engage in a dialogue with a bunch of kids about the pitfalls of narcotics, his perspective proved to be something that celebrated a life of addiction rather than shun it.
The Mad Real World
Air date: February 26, 2003
Much of what was created on Chappelle Show predated what we know today as social media, so often the comedian chose to focus on how reality television was warping our perspective on what was truly "real" versus what was staged and curated for public consumption.
While we had become accustomed to the faux-drama created on programs like MTV's The Real World - most of which centered on smiling white people dealing with the drama of being away from home for the first time - Chappelle's own version of "reality" registered as a slap at expectations when it came to casting those type of shows.
The Player Hater's Ball
Air date: March 19, 2003
The idea for "The Player Hater's Ball" stems from a real world counterpart, "The Player's Ball," which has found pimps from around the country gathering in locations like Chicago, Las Vegas, Miami and Atlanta to celebrate and crown the "Pimp of the Year" since 1974.
Chappelle's take didn't skimp on the excess and machismo associated with the illicit profession. But instead of focusing solely on the age-old profession, he injected his own brand of humor by making it a platform for the "most prestigious verbal abusers on the planet."
R. Kelly's "Piss On You"
Air date: March 26, 2003
Believe it or not, R. Kelly himself claims to not be familiar with Dave Chappelle's homage to the singer and his alleged reputation for engaging in watersports in the bedroom, despite attending the 2005 VMA's wearing a shirt reading, "I'm Rick James, Bitch."
Regardless of whether Kelly's claims are true or not, Chappelle's Show skewered the R&B singer by going so far as to insinuate that he was so enamored with that particular fetish, that he'd actually make a sensual music video to try and normalize it.
The Racial Draft
Air date: January 21, 2004
Named by Grantland as one of the four best sketches of all time, the Racial Draft closed out what would be the final official season of Chappelle's Show. Much like season 1's finale about Clayton Bigsby, the show once again chose to look at racial identity - this time commenting on how people often latch onto pop culture figures because they see a small part of themselves in them.
The Niggar Family
Air date: January 28, 2004
With "The Niggar Family" Chappelle created a Leave it to Beaver-esque television show in which an all-American family happened to have a surname which sounded like one of the worst racial epithets around.
Rather than solely going for the easy joke, the comedian also peppered the sketch with racial stereotypes about the family that were viewed as positives, given the color of their skin.
White People Dancing
Air date: February 4, 2004
Chappelle's Show will of course always be best remembered for its genius content from a comedy standpoint, but much can also be said for the musical portion of the show which saw notable performers like Mos Def, Talib Kweli, Busta Rhymes, Fat Joe, Killer Mike, Slum Village, The Roots, Wyclef Jean, De La Soul, Black Star, DMX, Cee-Lo, Kanye West, Common, Erykah Badu and Big Boi gracing the stage.
In "White People Dancing," Chappelle decided to combine the sketch and music elements of the show with a little help from Questlove and John Mayer, who helped the audience understand what types of music made certain races more inclined to start dancing.
Charlie Murphy's True Hollywood Stories - Rick James
Air date: February 11, 2004
If there is perhaps one single sketch that most people will bring up first when discussing Chappelle's Show, it's his unabashed love letter to both Rick James and the excess of the 1980s.
In an interview with VICE, Charlie Murphy confirmed what many suspected: the stories were 100 percent true, saying, "That story was a compilation of anecdotes that captured our relationship. But even if I did have more, to tell another one would be a discredit to the one you know. Because we all know that story is astronomically funny. If you hit a home run, you don’t think, 'Well, I’ll try and hit another one,' because you already did it."
In his 2004 special, For What It's Worth, Chappelle touched on the success of the sketch and eluded to his reluctance to embrace his growing star status. "I can see why stars are crazy," he said. The comedian went on to tell the audience what it was like to visit Disneyland with his children and having complete strangers walk up to him and say, "I'm Rick James, bitch!"
"Even Mickey Mouse did it," he cracked.
Charlie Murphy's True Hollywood Stories - Prince
Air date: February 18, 2004
Charlie Murphy's series of outlandish stories involving icons of the '80s and beyond continued when he spun a yarn that somehow involved Prince, pick-up basketball, and pancakes - serving as the comedic successor to the Rick James sketch which had aired a week earlier.
"That’s all true, except that Prince had sneakers on for the game," Charlie Murphy recalled. "He did actually change his clothes."
A Moment in the Life of Lil Jon
Air date: February 25, 2004
Continuing the momentum of music-related sketches, Chappelle and co. decided to examine some of the more modern influencers in the hip-hop genre when it came time to release the sixth episode of the second season.
At the time, Lil Jon was on a roll thanks to producing smash hits like the Ying Yang Twinz' "Salt Shaker," Usher's "Yeah!" and E40's "Tell Me When to Go" which were all enhanced by his high-energy ad-libs.
Having already portrayed everyone from R. Kelly to Prince, Chappelle's own take on Lil Jon proved to be another sketch that had people from all walks of life repeating what they had just watched.
If the Internet Was a Real Place
Air date: February 25, 2004
While there have been several copycats in recent years that imagined if Google and other sections of cyberspace were real, Chappelle's Show beat everyone to the punch when Dave and his staff imagined a scenario in which you could physically visit the Internet as if it was a mall.
Although the sketch is over a decade old, much of what Chappelle encountered continues to be hallmarks of the Internet's popularity in a contemporary context - ranging from pornography to free downloads.
"This place is sick," Chappelle says. "You should all be ashamed of yourselves. You heathens!"
Making the Band
Air date: March 24, 2004
Before the Kardashians ruled the airwaves, many people were eager to tune into MTV's Making the Band for their reality fix. The show chronicled the drama-filled exploits of a hip-hop group that Diddy seemed to form more out of his interest in the television format as opposed to the music that they were actually making.
The result was a target that was primed to be parodied by Chapelle, which mixed the faux-drama of reality television with the ego-maniacal tactics of Diddy himself.
The Wayne Brady Show
Air date: April 7, 2004
Paul Mooney's "Negrodamus" character on Chappelle's Show once quipped, "White people like Wayne Brady, because he makes Bryant Gumbel look like Malcolm X."
Part of the brilliance of Chappelle's Show is that the comedian never gave the viewer something that they could have predicted. Thus, when Wayne Brady made an appearance on the show, he allowed the veteran improv actor to create one of the best rebuttals in television history when he played an "elevated" version of himself.
"Every day, someone will come up to me and say, 'Does Wayne Brady have to choke a bitch?,' Brady recalls. "They say it on Twitter all the time, or I'll be walking down the street and someone says, 'I'm Wayne Brady, bitch.' It's cool, because it's great to have something in the zeitgeist. Not everyone can say they've done something that sticks around, and that's cool."
