Why Chappelle’s Show Will Always Be Important To Anyone With A Creative Spirit

8 insiders and fans celebrate the show’s legacy, a decade after it went off the air.

July 27, 2016
Comedy Central

Eleven years ago, Dave Chappelle quit his record-breaking TV show, impulsively hopped on a plane to South Africa, and chose peace of mind over millions of dollars. Two seasons of Chappelle's Show —the multi-format sketch show he'd created with comedian Neal Brennan— had made him a household name and turned his punchlines into a chorus echoed in cafeterias, living rooms, and frat houses around the world. As he explained years on, Chappelle had become consumed by a concern that his work, much of it using comedy as a vehicle through which to comment on race and class in America, was being decontextualized. His punchlines had become a punchline.


After Chappelle's eventual return, and without his participation, Comedy Central aired a brief third season of Chappelle's Show, a temporary salve for impatient, impassioned fans. Called the "Lost Episodes," almost like a TV equivalent of the posthumous rap albums that have dotted the genre's history, the final season was made up of just three episodes. Though Chappelle's Show ended the day its namesake walked away, this week marks 10 years since it went off-air for real. And in honor of that occasion, we asked nine people working in TV and film to share their personal connections to the man, the show, and its legacy.


Tyler, The Creator, artist and creator of Adult Swim's Loiter Squad

“I was Tyrone Biggums two years in a row for Halloween. I really love Chappelle. One, because he was funny, and two, we had the same body type: tall, lanky, skinny black guys. I had lanky arms that were always sulking and goofy, and the way he used his arms was something that I just learned how to emulate. It's weird. It made me feel cool about my dumbass long arms. I studied him and loved everything about him.


That was my guy growing up. And it's not like, ‘Oh I just thought he was really, really funny.’ No, I studied him and emulated him. I remember waiting for season three to come on and it never came on and then there were all these stories about him quitting but there was no real clarity. I was really confused for months; I was really bummed out.

Chappelle's Show really [influenced Loiter Squad], especially season three. Hell yeah. We was 12 years old watching his stuff, so that just really had an influence on how we wrote things and how we took our humor places. He was really smart for just the way he observed things; he wasn't throwing his take on you, he was just saying some shit he saw. Just looking at how he did that made me start observing my surroundings when I got older more and more.

When I finally got to meet him, in 2014, I fucking lost it. It was weird because he wanted a photo with me, and I thought that was the craziest shit ever. One day, me and my friends went to see his stand-up. It was like this back area, and it was my first time seeing him do stand-up. This nigga is talking to whole bunch of people and I guess he just looked up and he saw me from across the room, and he just literally stopped talking to everybody and came over to say what's up to me and my boys and kicked it with us. I thought that was the coolest shit. I love him so, so much. He's the best. I hope we can do something together one day.”

Jason DeMarco, Senior VP and creative director for on-air, Adult Swim

“I had been a fan of Dave Chappelle’s since his Killing Them Softly special way back in 2000. Even back then, Dave had honed into the things that would become the defining subjects of his career: being a black man in America, hip-hop, and relationships between men and women. Some of it was well-trod ground in the world of comedy, but Dave’s goofy, dry demeanor and offhanded way of delivering hilarious but brutal truths that lie at the heart of his best jokes stood out to me even then.

I tuned in for day one of Chappelle’s Show, and to me, at the time, it felt new and even somewhat dangerous in a way few comedy series have ever achieved. I mean, that first skit, ‘Clayton Bigbsy, White Supremacist,’ about the blind black man who thinks he’s a white supremacist, let you know pretty much right out of the gate this was not going to be a show that was afraid to take on race. Over the run of the series, from the Lil Jon skit (Yee-ayah!), to the R Kelly skit, to the racial draft, Dave, Neal Brennan and their writers kept finding ways to explore race, identity and politics in America, without a net. I think, looking back, it was a key moment for Comedy Central as a network in terms of relevance. And the influence of the show — particularly the way it mixed traditional skits, musical guests, and stand-up— is, I believe, wide and far-reaching.


Dave’s decision to end the show and walk away from (reportedly) a massive payday — because he felt like he was in danger of people misunderstanding what he was trying to to by bringing up the very real and important issues about race at the heart of his comedy — speaks of just how personal his comedy, and the show, was to him. Essentially, Chappelle’s Show was some of the realest comedy that has ever made it to TV. The fact that it became a hit is a miracle. The fact that its influence endures today, is a testament to something all of us who make TV know: great comedy stands the test of time.”

Chappelle’s Show was some of the realest comedy that has ever made it to TV. The fact that it became a hit is a miracle.”—Jason DeMarco
Keegan-Michael Key, actor and creator of Comedy Central's Key & Peele

“It really feels like yesterday that I was watching that show. People always ask if it was an influence to us [for Key & Peele] and it was. But it's the quality of the work that surpasses everything else. It wasn't necessarily that Dave was black; he was and he did a lot of racial stuff, but it was the execution that was so fascinating to me.

As we were doing Key & Peele, we'd get concerns like, ‘Did Chappelle do something like that?’ And one of our producers would say, ‘Please remember that Chappelle's Show has been off the air for six years.’ It was hard for you to fathom that that was the case; that was when YouTube was becoming more and more popular so you'd see his videos all the time and it felt like he was so present. It's funny how our landscape is different [today]; the thing that made his show get picked up was DVD sales. It's funny that that was only 10 or so years ago but it was an era where he was a juggernaut in DVD sales and that determined the life of the show.


There was always a wink or a sparkle in his eye that showed that he was having fun; so much of it was just really funny stuff. But I really appreciated the intelligence of what he was doing with the work. As much as there was silly stuff, there was also serious stuff and it was nuanced, certainly in theme if not in execution. I was thankful for his intelligence. Not every sketch was funny only because it was prurient or funny only because it was blue; he was always saying something in a clever way. The blind klansman sketch is one of the greatest sketches ever written. Ever written. It's just so brilliant.

He was turning cultural tropes on their ear. He was the first person I'd seen in a long time where he was using race to make a point culturally as much as he was making a point racially — maybe even more so. He was going, ‘I'm Dave and I'm mixing up the cultures.’ Because the writing was so clever, he was able to cross over [to less niche audiences] at the same time that he built his African-American audience. The fact that the quality was there meant that everybody and anybody could enjoy it.

In the end, whatever his reasons were, he always did whatever he thought was right for him and I admire that in a human. I've never met the man but I have a real affection for him. He really opened up my imagination and, more than anything, I want him to be happy and fulfilled as a human and as an artist.”

Lil Rel Howery, comedian and actor, The Carmichael Show

“You know what I love about Chappelle's Show? When it first aired, in the first three or four episodes, he always was saying, ‘They gon' cancel me after this.’ Chappelle had so many pilots that he worked on over the years that you get to a point where you're like, ‘I don't care anymore. I'm just gonna do whatever I wanna do.’ And you just hope you find a network that lets you have fun and be free. I used to be roommates with a bunch of comedians and all the comics used to come to our house and watch the show. It was genius.

He does things the way he wants to do it. Honestly, him and Kanye are a lot alike. I don't think it was ever about the money for him. I think it was always an artistic-driven thing. And it was just ‘truth’ writing. He wrote those sketches and didn't care about how anybody felt. Instead of getting picked on, he got praise for it. It makes you proud of Chappelle when you think about it. I'm proud of the fact that you didn't even have to be on for five or six years; you did three really strong seasons and set the world on fire. You knew after that first episode, that this was gonna change the game. You knew it!”

Damilare Sonoiki, writer, black-ish

“I remember being a a kid and watching Chappelle's Show. I was in sixth or seventh grade when it first came out and I remember coming to school and me and my friends would just repeat all the worlds to each other. It was very funny but also it made fun of things that I don't think a lot of shows made fun of — the show lived in a vacuum. It was making commentary about race that other shows weren't making.

For me, [the legacy] is like how people now are appreciating the scene from Fresh Prince where Jazz keeps his hands up in the courtroom because [he's afraid he's gonna be shot by police]. But at the same time, Chappelle's Show wasn't preachy at all. There were silly sketches, like ‘Making the Band’ and he was just good at satirizing and doing stuff that was flat-out funny without always needing a message. More than anything, the inspiration for me is to make something that's filling the vacuum of Chappelle's Show. It's aspirational; to create something as well-received and as having even half of that impact would be cool.”

“He was turning cultural tropes on their ear. He was the first person I’d seen in a long time where he was using race to make a point culturally as much as he was making a point racially.”—Keegan-Michael Key
King Bach, internet personality and Vine comedian

“My first memory [of Chappelle’s Show] was the Rick James sketch. I was in tears while I was watching it. It was a unique show. There was nothing like it at the time. It definitely pushed the envelope of comedy. It made me unafraid to take risks. Dave Chappelle took a lot of risks with his comedic sketches and a lot of them worked. I started applying that to my own comedy when making sketches and did not fear failure.”

Lena Waithe, actor, Master of None

“To me, Chappelle's Show felt like a throw back to The Flip Wilson Show — it was political and funny at the same time. And even though it could be topical, the show never feels dated when you revisit it. Whenever I watched it I always got the feeling that Dave wasn't afraid of anybody. Like, he wasn't in anyone's pocket. And that's huge for black artists. Because we were getting his message loud and clear: No filter. He was the personification of artistic freedom.”

Sasheer Zamata, actor and comedian, Saturday Night Live

“I loved watching the show. It was such a great talking point that was a ‘water cooler’ conversation for years, especially for me as a teen. A sketch that sticks out that I just referenced recently was the Wayne Brady sketch where he's riding around with Wayne Brady in a car and it turns out the squeaky clean Wayne Brady is actually really dangerous. I also loved Wayne Brady in general — I was a huge fan of Whose Line Is It Anyways? — and to see the combination of those two comedians was so fun. It gave Wayne Brady a ton of street cred that he didn't have before and maybe introduced him to people who didn't get his humor. I loved seeing these black comics support each other. No matter how different their styles were, that showed that they could have fun in a sketch together and make fun of each other.

Chappelle was really good at picking out pieces of society that people were scared to talk about and highlighting them in a way that would be to the extreme. Things that people would not want to talk about, he was good at bringing it to the forefront in a way that was hilarious. That's probably why it resonates still because these are still issues that we're working on. I've always admired his truthfulness and his ability to pick apart what you think is funny about something that may be a rough issue.


I also thought he had great taste in music. I remember Erykah Badu performed on his show. One of her performances sticks out to me: her hair was just so huge, the camera did this slow zoom into her face and it was just so hypnotizing and sexy and I just remember feeling like, Whoa, this is amazing. I was already in love with her and the show and seeing this on Comedy Central was just so cool.”

Why Chappelle’s Show Will Always Be Important To Anyone With A Creative Spirit