The opening episode featured a bit about a character named Clayton Bigsby, a blind guy who hated black people but didn’t know he, himself, was black. The premise was hilarious, the execution was even funnier and, on a certain level, it made you think. That formula never went dry.
Over the course of two seasons, the show featured a handful of unforgettable characters: Negrodamus, played by Paul Mooney; Tyrone Biggums, the crack addict with a heart, played by Chappelle himself; and of course, Ashy Larry, played by Donnell Rawlings.
I caught up with Rawlings, who is in Los Angeles working on new shows as part of MTV2's "Guy Code" brand, on the phone to talk about the decade that's passed since that first episode aired. Rawlings, a D.C. native like Chappelle, had almost forgotten it had been that long.
"It's weird because I forget that it was 10 years," Rawlings said. “I travel across the country, and I come in contact with fans and people that enjoyed the show, it always feel like the show was just on two years ago.”
Since the somewhat strange end of the program, Rawlings has been touring as a comedian and making appearances in television and film. He even did a stint in the District as a co-host on WPGC 95.5's "Big Tigger Morning Show" from 2010-2011.
But how he even got involved with Chappelle’s program is a rare Hollywood story of two people doing each other a solid. When Neal Brennan, co-creator of "Chappelle's Show," was working as a production assistant and cameraman for "In Living Color," he met Rawlings on a nationwide audition search for comedians.
When Brennan needed actors for a short film project he was doing to build up his reel, he asked Donnell to be a part of it. " I told him I know that you really don't have money to pay me, but if you're ever in a situation where you could throw me a bone, do it," Rawlings said. "And I'd say maybe five months after that, he was working on "Chappelle's Show" and he called me, and of course with Dave's approval, but [Neil] was the one that endorsed me or introduced me to the show."
But that didn’t mean that it was a done deal as for Rawlings’s road to eventual stardom. The environment on the show was competitive and Chappelle's ability to give certain comedians an opportunity was not lost on anyone.
"I don't know if every comic could’ve performed at that level or had the creativity to make it happen. I think it was a special show, with special people, and it had a special opportunity. It was just a challenging show," said Rawlings, a graduate of T.C. Williams High School in Alexandria. "Nobody was guaranteed. Nobody was a cast member. On that show, it was like you were as good as your last sketch."
It's not easy to put into words how "Chappelle’s Show" affected my life. But I will say that I can't imagine what I'd be like today without it. The program resurrected the concept of 'catch phrases' and gave D.C. some shine when there weren’t a lot of things on the national scene with local roots.
When Chappelle busted out the line "We rocked them ’bamas!" in the "Black Bush" sketch at the end of Season 2, it was the first time I'd ever heard that word on national television and it felt good.
On a larger level, "Chappelle's Show" set a new bar for how we were allowed to look at our differences while still taking one another seriously, an important step in terms of the American discourse. And not surprisingly, there are catch phrases from that show that still permeate our society.
"I'm rich, bi-atch!" perhaps the most famous one comes from Rawlings, who still feels like as important a member of the program as any. "So as much as people think the show made me, I think my contributions helped make a successful show. I'll say I was the sixth man," Rawlings said of his time there. "Your coach is not going to keep putting you in the game if you're not being productive."
There might be something close to “Chappelle’s Show” again, but not anytime soon. The cultural zenith that was one half-hour midweek show on a basic cable network is going to be tough to replicate. And 10 years later I still think of it the way Rawlings described his experience with the show.
“That show was…you can print this, it was the [expletive], man."
Yates is a columnist for TheRootDC