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The Rise and Fall of Chappelle’s Show

Chappelle’s Show is the greatest sketch comedy of all time. There, we said it. We can already hear the proverbial groans of disagreement. What about the G.O.A.T. Saturday Night Live…you know Belushi, Murphy, Ferrell? Well, let’s see the legendary SNL become a cultural phenomenon in the age of cable TV and shrinking Nielsen ratings. But Dave can’t fuck with the Wayans family’s multicultural breakthrough In Living Color. Sure Dave owes a lot to Keenan. But In Living Color overstayed its welcome, while Chappelle’s Show left a pristine corpse, a la Jimi Hendrix and Tupac. Mad TV? You’re kidding, right? Really, who cares why Dave bailed out of his landmark show. He can go on Oprah and Inside the Actors’ Studio and explain his meltdown all he wants. His show shouldn’t be, and isn’t, defined by his abrupt exit or self-medicating trip to Africa. Its tombstone should read: Here Lies the Comedy With the Biggest Balls. Period.

Season One

Chappelle’s Show premiered on January 22, 2003

The Mad Real World

Christian Finnegan (“Chad”): I’m a standup comic, and so was Neal. One day, he was like, “You know, I’m doing this show with Dave, and we’re doing this bit that you might be really good for.” When you get cast for something like that, you have to sit down for a table read together, and read the script out loud. It was that sketch, the Clayton Bigsby sketch, and something else. Everybody was looking around the table like, “I can’t believe how funny this is.”

Charlie Murphy (comedian, actor): People liked the [tough] characters I did from CB4, Players Club and Spike Lee’s films, and when people would think of someone playing a gangster-type role, my name would come up at the top of the list. So when they were writing “The Mad Real World” sketch Dave was like, “Yo, we need Charlie Murphy to play this thug- ass character named Tyree.” That was my first sketch.

Finnegan: No one ever comes up to me quietly and says, “Hey, I really enjoyed your work in ‘The Mad Real World.’” People walk up to me in the middle of a dinner with my girlfriend like, “Katie’s got some big-ass tittays!”

Ask A Black Guy/ Negrodamus

Paul Mooney (comedian, writer, actor): I basically came up with “Negrodamus” and “Mooney On Movies,” while Dave came up with “Ask A Black Guy.” “Negrodamus” was actually supposed to be Niggerdamus, but we had to clean it up. You know when I say “nigger,” it’s like the devil is saying it [laughs].

Player Haters’ Ball

Bryan Tucker (writer, “Player Hater’s Ball”): Dave and Neal have a good idea, and they have a set-up, and then they do like 10 takes. Dave does a little something different every time. So a lot of the great lines you see aren’t necessarily stuff that you’d see written in a script.

Donnell Rawlings (comedian, actor; Ashy Larry): Ten minutes before we go shoot “Player Haters’ Ball,” my character didn’t have a name or anything. I went to hair and makeup, told them to give me a Jheri-curl wig. Then I went to props, and I asked for a Moët bottle with an activator on it so I can just squirt my hair down. They didn’t have that, so they gave me the aerosol can. I’m spraying it, people laughing and shit, three minutes before shooting. I didn’t have a name, dialogue or anything. Neal told me to make my name up. I walked past the mirror like twice, looked in it, and said, “Man, I feel beautiful!” That’s when “Beautiful” was born.

Bill Burr (announcer, “Racial Draft”): Dave and Neal were real cool with improv. They were like, “If it’s funny, it’s going in.”

Rawlings: Dave always does something to let everybody know why it’s Chappelle’s Show. When he got to the page flip, we had already had 18 hours in. It had to be like 2:30, 3 in the morning—we was all joked out! Dave was the only one who kept it moving. “She look like she wear underpants with dickholes in them!” That was the end of that. It’s a wrap. Let’s go home.

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