Considered by many to be one of the greatest sketch comedy shows of all time, Chappelle’s Show tackled race, contemporary issues, and the misadventures of Eddie Murphy’s older brother in an unflinching—and hilarious—way. The show’s meteoric rise in popularity during its second season led to its star, Dave Chappelle, signing a massive contract, only to then retreat from the spotlight, resulting in the show’s cancellation, which permanently cemented its place on the list of beloved television shows that ended too soon. Here are some facts about the show no player could possibly hate on.
1. HUGH HEFNER INSPIRED DAVE CHAPPELLE TO CREATE THE SHOW.
One night, Dave Chappelle watched a special on Playboy publisher Hugh Hefner that was designed to resemble one of Hefner's Playboy parties. The host of the party interviewed musicians and comedians, who would then perform for Hef, some Playboy Bunnies, and other guests. On Inside the Actors Studio, Chappelle told James Lipton that he was weirdly inspired by it and called his Half Baked (1998) co-writer Neal Brennan to talk about it. “We started talking about variety shows, we wanted to do something that was real personal,” Chappelle recalled of their conversation, which led to the creation of Chappelle's Show.
2. HBO PASSED ON THE SHOW.
“We pitched to HBO and they looked at us like we were lepers,” Brennan recalled to Free Press Houston.
3. CHAPPELLE AND BRENNAN LEARNED HOW TO WRITE THE SHOW BY READING A BOOK ABOUT SATURDAY NIGHT LIVE.
The two read Live From New York: The Complete, Uncensored History of Saturday Night Live as Told by Its Stars, Writers, and Guests, the oral history of the iconic sketch show compiled by James Andrew Miller and Tom Shales, before shooting the pilot and writing sketches for the first season. Brennan found the book to be “really informative and really helpful.”
4. DONNELL RAWLINGS CAME UP WITH HIS PLAYER HATER'S BALL CHARACTER ON THE FLY.
In an interview with King magazine, writer/actor/comedian Donnell Rawlings shared that his Player Hater's Ball character didn't come together until the very last minute. "I went to hair and makeup, told them to give me a Jheri-curl wig," he explained. "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."
5. WAYNE BRADY DIDN’T LIKE WHAT NEGRODAMUS SAID ABOUT HIM.
Wayne Brady was a fan of Chappelle’s Show and never missed an episode. But when he watched Paul Mooney, as Negrodamus, say “White people love Wayne Brady, because Wayne Brady makes Bryant Gumbel look like Malcolm X" in a sketch, he got upset. After buying drinks for some of the crew of the show at the NAACP Image Awards, Brady brought up his feelings about the sketch. Chappelle called him the next day, which led to a famous sketch in which Brady shows off his dark side (below).
6. CHAPPELLE WASN’T PLANNING ON PLAYING SAMUEL L. JACKSON IN THE SAMUEL JACKSON BEER COMMERCIAL.
"We cast people, they'd do it, and we knew that wasn't how it needed to be done," Brennan recalled. "Dave knew how he wanted it so he just would do it. Instead of counting on someone else to capture our imagination, we just did it ourselves."
7. THE GUY DOING THE ROBOT WAS THE SHOW’S SET DESIGNER.
Karl Lake first found his way in front of the camera during an And-1 sketch. "We thought it would be funny if people were just bugging out," Brennan told The Root. "To heighten the bug out, [set designer] Karl Lake just started doing the robot. It's so dumb that we kept doing it, and it just became a thing."
8. THEY FILMED THE RACIAL DRAFT SKETCH ACROSS THE STREET FROM JAY Z’S (THEN) FINAL CONCERT.
RZA disappeared for one hour during the shoot, delaying the production. He came back and explained he went over to Madison Square Garden to watch some of the concert.
9. BOBBY BROWN WAS GOING TO DO THE STD PUPPET SCENE, BUT HE GOT ARRESTED.
To replace Brown for the Kneehigh Park sketch, they called Andre 3000 and Pharrell, with no luck. Q-Tip said yes, and Snoop Dogg went from being cast in a “Weed Olympics” sketch that got cut to get involved, too.
10. IT’S CREDITED WITH MAKING LIL JON POPULAR.
Chappelle's “A Moment in the Life of Lil Jon” sketch launched the hip-hop artist into superstardom. “This Dave Chappelle sh** just really put me on a different level," Lil Jon told MTV. "He basically has thrusted me into pop culture, and not just urban but white society as well. I was in the airport like three weeks ago, this 60-year-old white lady came up to me and was like, 'Aren’t you Lil Jon? … Don’t you do that 'Whuuuut? Yeeeaaah! Okaaayyy!' That’s you, right?’” After Chappelle witnessed fans shouting lines from the show at Lil Jon at the MTV Video Music Awards, Chappelle apologized to him.
11. CHARLIE MURPHY GAVE CHAPPELLE THE IDEA FOR THE RICK JAMES SKETCH OVER LUNCH.
Charlie Murphy and Chappelle were at the lunch table during a break from shooting the “Calvin’s Got a Job” sketch. Murphy regaled the table with his stories about hanging out with Rick James when Chappelle said it should be reenacted for the show.
12. EDDIE MURPHY THOUGHT THE RICK JAMES SKIT WAS GENIUS.
Charlie showed his brother the sketch. Eddie Murphy watched the whole thing in silence. Once it ended though, he said it was “genius” before laughing and insisting Charlie play it again.
13. CHAPPELLE AND RICK JAMES HAD MET YEARS EARLIER.
A then-19-year-old Dave Chappelle was in Los Angeles filming Robin Hood: Men in Tights (1993). Young Dave and James hung out at the hotel bar together a few times. The sketch ultimately led to some problems for a politician named Rick James; when he ran for city council in Hattiesburg, Mississippi in 2005, many of his campaign signs were stolen or defaced by people who added the word “b*tch!” James claimed he saw signs of his as far as 100 miles away.
14. PRINCE GOT HIS REVENGE.
The singer/songwriter confirmed the story about beating Charlie Murphy at basketball, which was ultimately turned into a sketch. But Prince claimed that it wasn’t because he was particularly good at the sport; it was because Charlie Murphy was bad.
In 2013, Prince released his single “Breakfast Can Wait” with a picture of Dave Chappelle dressed as Prince from the show on the cover. “What am I going to do—sue him for using a picture of me dressed up like him?” Chappelle asked rhetorically at the time.
15. CHAPPELLE GREW FRUSTRATED AT STAND-UP AUDIENCES SHOUTING LINES FROM THE SHOW.
He infamously told a 2004 stand-up crowd that they were “stupid” for shouting “I’m Rick James, b*tch” when he was trying to perform, and told them that the show was ruining his life. Chappelle later walked away from a reported $50 million contract before recharging his batteries in Africa. He appeared on Oprah in 2006 and said he felt manipulated by those around him. "I felt in a lot of instances I was deliberately being put through stress because when you’re a guy who generates money, people have a vested interest in controlling you,” he said. He told Comedy Central he wanted to restructure the deal and to give his money away to help people. Instead, the network aired an abbreviated “lost episodes” third season using the footage that had been shot, hosted by Rawlings and Charlie Murphy.