15 Fun Facts About Chappelle's Show

Comedy Central
Comedy Central

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 series, which premiered 15 years ago today.

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.

Not everyone was immediately sold on the concept. “We pitched to HBO and they looked at us like we were lepers,” Brennan told 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 said the book was “really informative and really helpful” to them.

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. “Ten minutes before we go shoot ‘Player Haters’ Ball, my character didn’t have a name or anything,” Rawlings said. “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 Moét 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 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.

6. CHAPPELLE WASN’T PLANNING ON PLAYING SAMUEL L. JACKSON IN THE SAMUEL JACKSON BEER COMMERCIAL.

Dave Chappelle and Bill Burr in 'Chappelle's Show'
Comedy Central

"We cast people, they'd do it, and we knew that wasn't how it needed to be done," Brennan said. "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 super-stardom. “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, who passed away in 2017, 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.

Dave Chappelle
Christopher Polk, Getty Images

Chappelle 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.

Chappelle 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.

15 Facts About Rushmore On Its 20th Anniversary

The Criterion Collection
The Criterion Collection

On December 11, 1998, Wes Anderson introduced the world to his unique brand of whimsical comedy with Rushmore. Though it wasn't his feature directorial debut—he had released Bottle Rocket, which he adapted from a short, in 1996—it was his first major Hollywood movie. And kicked off his still-ongoing collaborations with a stable of talented actors that includes Bill Murray and Jason Schwartzman. It was also the second film Anderson co-wrote with Owen Wilson.

To celebrate the quirky comedy's 20th anniversary, here are some things you might not know about Rushmore.

1. Rushmore Academy was the director's Alma Mater.

Wes Anderson sent location scouts across the United States and Canada to find the perfect high school to shoot the movie. He was having a tough time trying to find the school, until his mother sent him a picture of his old high school in Houston, Texas: St. John's School. Anderson thought it was the perfect location to make the movie.

2. Bill Murray wanted to make Rushmore for free.

Bill Murray in Rushmore (1998)
The Criterion Collection

Once Bill Murray read the screenplay, he wanted to be in the movie so badly that he considered appearing in it for free. Murray ended up working on Rushmore at scale with the Screen Actors Guild day rate minimum for smaller indie film projects. Anderson estimated that Murray made about $9000 for his work on the film.

3. Film critic Pauline Kael had a private screening.

Pauline Kael’s film criticism was a major influence on Anderson’s view of cinema. “Your thoughts and writing about the movies [have] been a very important source of inspiration for me and my movies, and I hope you don't regret that," he once wrote to her.

Kael retired from The New Yorker in 1991, so Anderson arranged for her to have a private screening of Rushmore before the film came out in 1998. He wrote about the screening in the introduction to the published version of the screenplay, and shared what Kael told him about the film: "I genuinely don't know what to make of this movie."

4. It was Jason Schwartzman’s first film role.

Casting directors searched throughout the United States, Canada, and England to find a young actor to play the lead role of Max Fischer. Australian actor Noah Taylor was the frontrunner for the part when, on the last day of casting in Los Angeles, Jason Schwartzman auditioned. He was wearing a prep school blazer with a Rushmore Academy patch that he made himself.

5. Owen Wilson's private school experiences inspired some of the movie's plot points.

As a sophomore at St. Mark High School in Dallas, Texas, Rushmore co-writer Owen Wilson was expelled for stealing his geometry teacher's textbook (the one that contained all the answers); he went to Thomas Jefferson High School to complete 10th grade. This was the inspiration for when Max is expelled from Rushmore Academy and is forced to attend Grover Cleveland High School.

Although Wilson doesn’t have a credited role in Rushmore, he does appear as Ms. Cross’s deceased husband, Edward Appleby, in a photo in Appleby’s childhood bedroom.

6. Wilson's Dad Inspired a Moment in the Movie.

Wilson’s father, Robert Wilson, was the inspiration for Herman Blume’s speech about privilege at the beginning of Rushmore.

7. Alexis Bledel was an extra in the film.


Getty Images

Before she starred as Rory Gilmore on Gilmore Girls, actress Alexis Bledel was an uncredited extra—she played a Grover Cleveland High School student—in Rushmore. You can see her in the background in various scenes, including dancing with the character Magnus Buchan (Stephen McCole) at the end of the film.

8. Both Anderson and Wilson's brothers had parts in the movie.

Owen and Luke Wilson’s older brother Andrew plays Rushmore Academy’s baseball coach, Coach Beck. He also appeared in Anderson’s directorial debut, Bottle Rocket, playing the bully John Mapplethorpe.

Eric Chase Anderson, Wes's brother, plays the architect who designs Max’s aquarium.

9. The Movie's Editor Made a Cameo.

Rushmore editor David Moritz plays the Dynamite Salesman; he sells Max the dynamite and explosives for his stage play Heaven and Hell at the end of the film.

10. Producers Made a Deal to get a Bentley.

Producers needed a Bentley for Murray's character, Herman Blume, but Rushmore’s production budget was only $20 million and they couldn’t afford to rent one. A Houston resident was willing to lend them his Bentley if they gave his daughter a role in the film. Producers agreed; the man's daughter plays an usher who seats Miss Cross at Max’s play at the end of the movie.

11. Mason Gamble's role in Dennis the Menace almost cost him the part of Dirk Calloway in Rushmore.

Mason Gamble in Rushmore (1998)
The Criterion Collection

Wilson referred to the character of Dirk Calloway, played by Mason Gamble, as the conscience of the film. Originally, Anderson didn’t want to cast Gamble in the part because of the actor’s previous—and very recognizable—role as Dennis Mitchell in the 1993 live-action movie Dennis the Menace.

12. Rushmore Upset Francis Ford Coppola.

Director Francis Ford Coppola owns a winery, and when he first saw Rushmore, he was upset with Anderson because he used Coppola’s chief Napa Valley wine rival during Max's post-play celebration. (It probably didn't help matters that Coppola is Schwartzman's uncle.)

13. Anderson's Brother Did the Movie's Criterion Collection Artwork.

The Criterion Collection edition of 'Rushmore' (1998)
The Criterion Collection

Eric Chase Anderson did the artwork for the Criterion Collection DVD cover, an interoperation of a shot from the montage of Max’s extracurricular activities at the beginning of the movie. The Yankee Racer shot is itself a recreation of a photo from French photographer Jacques Henri Lartigue, taken in 1909 when he was only 15.

14. Schwartzman waxed his chest to play Max.

Although Max only shows his chest once in the film (during the high school wrestling match), Anderson made Schwartzman wax his chest for the duration of Rushmore's filming.

15. The Max Fischer Players Appeared on MTV.

During the 1999 MTV Movie Awards, the Max Fischer Players recreated the year's hit movies—The Truman Show, Armageddon, and Out of Sight—as stage plays.

An earlier version of this article ran in 2014.

Harry Potter Star Daniel Radcliffe Says Broadway Made Him a Better Actor

Dominik Bindl, Getty Images
Dominik Bindl, Getty Images

For 10 years, moviegoers watched as Daniel Radcliffe matured on film throughout eight Harry Potter films. But the 29-year-old recently revealed that he believes the bulk of his professional growth has occurred as a result of his Broadway stage work.

“It gives me a lot of confidence as an actor, which is not always something that I’ve felt,” Radcliffe told Variety. “I feel like doing theater ... it was really very important for me psychologically.”

Radcliffe starred in a number of films after Harry Potter and the Deathly Hallows: Part 2, the final film in the franchise, including The Woman in Black, Now You See Me 2, and Lost in London. His Broadway credits include Equus, How to Succeed in Business Without Really Trying, and The Cripple of Inishmaan.

“There’s something about doing it without an editor to save you, or a myriad of things in post-production that can help you out, something that made me go: ‘OK, I can act,’" Radcliffe continued. "I’ve grown a little bit as an actor every time I’ve gone back to the theater."

Radcliffe crediting his professional growth to working in theater may leave some Potterheads wondering if he thinks playing Harry Potter for so long held him back.

“Not professionally, at all,” he said. “There were moments when probably I coped with the personal effects of Harry Potter not as well as I could have. But professionally, no.”

According to Radcliffe, "There are directors that were, I think, excited to—I am quoting one of them here and I won’t say who—'reinvent' me.”

Radcliffe fans can gauge that reinvention for themselves with The Lifespan of a Fact, the new Broadway play starring Radcliffe, Bobby Cannavale, and Cherry Jones. It is running at New York City's Studio 54 through January 13, 2019.

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