It’s been 10 years since the debut of Chappelle’s Show. January 22nd marked the 10th anniversary of its premiere, and it’s hard to believe that a full decade has passed since this groundbreaking show premiered on Comedy Central. However, it only lasted two seasons. Comedy Central tried to piece together a few episodes for a third season, but essentially it was all over very quickly.

Even more sadly, many people reduced the show to a simple catch phrase. Go to any bar or restaurant and start a conversation about Chappelle’s Show, and one person will inevitably say, “I’m Rick James, bitch!” His/her friends will all chuckle at what they thought was a witty one-liner, and you’ll smile and pretend that the person who said it isn’t a complete asshole. While the show had plenty of humor for the masses (he once had a choir singing the “diarrhea song”, dedicated to the many critics who initially dismissed his show as “juvenile”), it was the satire and social commentary that got others hooked. That’s the side of the show I’ve chosen to focus on as we reminisce about the good old days of 2003-2004.

The debut episode featured the now-famous “Clayton Bigsby” skit. Set as a Frontline episode, Clayton is the nations (presumably) only blind & black, white-supremacist leader.

The show then went on each week, much to Dave’s surprise, that the show hadn’t been cancelled. The opening monologue in many of the subsequent episodes usually involved something to the effect of “Thanks for joining me, I see we haven’t been cancelled yet…”

It featured skits involving alternate endings to real movies, Roots outtakes, reparations for slavery, celebrity endorsements (Roca-Pads, Wu-Tang Financial), Ask A Black Dude, the Jedi Sex Scandal, and of course the recurring character of the lovable crack head Tyrone Biggums. And how could we forget the “Mad Real World?”

Probably the most memorable skit from Season 1 is the R. Kelly video of Piss On You.
It really needs no introduction.

The first season closes out with Fistcuffs – a rapper who got shot eight times in the ear, and an interracial edition of Trading Spouses.

The second season is where Dave hits his stride. The first episode of the season (Episode 13) is the racial draft episode, where Tiger Woods officially becomes black, Colin Powell & Condoleezza Rice are officially white, and the Wu-Tang are officially Chinese. It’s finally settled!

Episode 14 features a Leave It To Beaver-style sitcom parody featuring a white family named the “The Niggar Family,” as well as the introduction of “Negrodamus.”

Do you ever wonder what would happen if street criminals had to deal with the legal system that white collar criminals have, and the heads of Enron & Tyco had to deal with the legal system that drug dealers have? Look no further:

Ok, it’s time for a story. A few years ago, I had a 20-year-old coworker (let’s call her “Jan”) who came in one day with a big smile on her face. She was usually a grouch, so this was completely out of character for her. Someone asked, “Why are you so happy today?” To which she rubbed her belly and exclaimed, “I’m pregnant!”

We all congratulated her, some of us were genuinely happy for her; some of us were indifferent, but polite. After several coworkers left, there was just Jan, myself, and 2 other employees, lets call them Bob and Ricky. Bob and Ricky got along with Jan well, so she opened up to them.

“So how did this happen?” Bob asked.
“What do you mean?”
“I mean, you and your boyfriend have only been going out about a year. I didn’t know you were planning to have kids just yet – not that there’s anything wrong with that.” Bob explained.
“Well, he doesn’t know yet. I’m going to tell him when he gets here in about a half an hour. And I’ve been wanting a baby for a long, long time.”
“Does he want one too?”
“I hope so.” She answered.
“You hope so?”
“He thinks I was on the pill. I stopped taking it about a month ago, but I didn’t tell him.” She then smiled a let out a “hehe” giggle.
“Wait, so let me get this straight, you decided that you wanted a baby, and so you got pregnant deliberately, without consulting your boyfriend?”
“I want a baby!” she said. “He’s from a good family, and he’s got money. I’m not stupid!”
“Yes you are.” I thought to myself
She then said, “Don’t you guys dare tell him any of this. It’s our little secret.”
“Ok, so after you tell him you’re pregnant, what are you going to tell him if he questions whether or not you’ve been taking the pill all this time?”
“I’ll just say, ‘honey, you know I’ve been on the pill, but you know its not 100% effective. There’s always a small risk. So, it looks like we have a little miracle here.” She then rubbed her belly again and smiled.

Jan was so proud of herself for figuring out how to manipulate this situation. As soon as she told her boyfriend, she put in her 2 weeks notice, and nudged her way into moving in with his family. I suspect he knew she was a liar, but what can a guy do?

Jan is hardly the first girl to use pregnancy as a way of roping in a guy for financial stability, and that brings me back to Chappelle’s Show. Chappelle loves to turn the tables on race, but here’s an example of him turning the tables on gender. In Episode 21, Dave gets Oprah pregnant. He instantly quits his job, tells everyone to kiss his ass, then makes her fly him out to Chicago so he can live in her mansion, spends her cash, and live like a king. Check this out! Genius!

Then Dave starts doing a show of outtakes. It is the beginning of the end. One great clip here is when the Playa Haters go back in time to the days of slavery. However, looking at this clip from 2004 looks eerily similar to a movie I just saw with Jamie Foxx. Check this out.

Then it gets really weird. Towards the end of Season 2 (episode 24, to be exact), it opens with Dave meeting with Comedy Central executives. In what can only be assumed to have been based on actual events, he quits. Dave says he’s burnt out, and Comedy Central threatens to replace him. Dave calls their bluff and inevitably gets replaced by Wayne Brady for the infamous “Wayne Brady Show” episode: Wayne hosts, has his own theme song, charms the audience, and proceeds to “burn through” the rest of Dave’s prerecorded sketches before launching into season 3, which (he says) will be called the “Wayne Brady Show.” You dig?

Dave and Wayne, toward the middle of the episode, decide to co-host the remainder, and this is where we get an inside look at the “real” Wayne Brady:

The final episode of season two ends strongly on the premise of what would happen is George W. Bush were black:

This concludes the second season, and the last of the “proper” Chappelle’s Show episodes. It would be two full years before we would see a “new” episode. During that time, there were rumors that he had gone insane, that he was burnt out, that he was in therapy, and (my favorite) that he had flown to South Africa with the $50 million advance for the 3rd season and was never coming back to the States.

In early 2006, Chappelle appeared on Oprah, and gave us hope that a third season would materialize. He had certain prerequisites that he required of Comedy Central, and also announced that if Comedy Central aired the then-unaired episodes, he would not come back and do the show.

Needless to say, Comedy Central aired those episodes in what are now called “The Lost Episodes.” Many of these skits pale in comparison to the previous seasons, which is probably why Dave didn’t want them to be broadcast. Some of them had to do with Dave adjusting to fame and fortune. There are some great moments, though, like this one where Dave gets revenge on an old girlfriend, an old casting agent who said he didn’t have “it”, and a club owner who banned him before he was famous.

I’d like to close this out with some of Dave’s standup. Dave started, and continues to be, a thought-provoking stand up comic. This bit, although it mentions the R. Kelly scandal, is NOT about the R. Kelly scandal. Like much of Dave’s work, if you think that, then you missed the real point. Pay attention to the bigger picture here. And above all, laugh, and enjoy!

And thank you, Dave Chappelle!

Bonus: Make sure you check out Grantland’s excellent bracket-style battle for the best Chappelle’s Show sketch of all time.

Bonus Bonus: Our own list of the best Chappelle’s Show skits of all time.

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