Comedian Dave Chappelle shows little discrimination when choosing the targets of his acerbic wit. And yet somehow, no one has been able to bring Chappelle’s own personal life into the fray. Well, it’s hard to get the dirt on the Chappelle family: They’re holed up in Ohio surrounded by a buffer of farmland as far as the eye can see. I think it’s time to deep dive into the facts about Dave Chappelle and find out what he’s hiding.
1. They Were Serious
David Chappelle—or David Khari Webber Chappelle as his parents named him—was born in Washington DC on August 24, 1973. Chappelle’s parents were both professionals. His dad was a music professor and his mom was many things: a Unitarian Minister, a professor of history, she even worked in the cabinet of the prime minister of the Democratic Republic of the Congo.
With parents as accomplished and serious as his, you may wonder how Chappelle ended up in comedy. Well, while his parents may have been working stiffs, they had some seriously good connections.
2. He Guessed Right
Chappelle’s parents were both politically active, but also found time to have music in their lives. While growing up in Silver Spring, Maryland, the Chappelles had musical visitors to their home. Social activist and musician Pete Seeger dropped by from time to time, and so did jazz singer Johnny Hartman. Hartman saw something in young Dave Chappelle and even made an ominous prediction: Chappelle would be a comedian one day.
3. He Was Obsessed
It actually wasn’t that difficult for Hartman to make the prediction about Chappelle, because as a child Chappelle was obsessed with comedians like Eddy Murphy and Richard Pryor. Well, it was good that Chappelle had a sense of humor—he’d need it for his next few years. Sadly, Chappelle's parents separated, and Chappelle began a new life with a difficult arrangement: Summers with his dad in Ohio and the rest of the year with his mom in Washington.
4. He Was Random
In spite of his difficult home life, Chappelle was getting more and more serious about being a performer of some kind. To make this happen, he switched from a regular high school to Duke Ellington School of the Arts. Before Chappelle even graduated from high school, he had his first TV appearance. America’s Funniest People was a spin-off of the immensely popular America’s Funniest Videos. In 1990, a 17-year-old Chappelle got a chance to show off his humor.
However, when Chappelle sat in front of the TV to see himself, he was in for a disappointment: The show had buried his spot in a montage alongside many random people telling jokes. Chappelle, however, had the bug, he knew wanted to make people laugh.
5. It Wasn’t The Plan
Chappelle quickly figured out that neither his father’s town in Ohio nor Mom’s place in Washington was where he could get his comedy career going. He high-tailed it to New York City and didn’t waste any time. He heard that the famous Apollo Theater in Harlem had an amateur night, so he got himself there and performed his first set. Let’s just say it didn't go quite as planned.
6. So, That Happened
Probably the last thing Chappelle wanted to happen at the Apollo Theater, actually happened. The audience booed him off the stage. Devastating for most people, but not Chappelle. He turned this horrible incident into something positive. He said that it gave him the courage to continue on with his career. Once you’ve faced a theater full of people who want you to stop performing, I guess you can do anything.
And “anything” apparently included working in rather nontraditional places.
7. He Worked In Parks
Instead of licking his wounds from the Apollo Theater debacle, Chappelle took to performing with a vengeance. He rarely missed an opportunity to tell jokes. This included even trying to amuse random people in public parks. Soon, Chappelle was becoming known in New York’s comedy community. He started getting gigs in actual theaters and continued working at open mic nights. Sure, Chappelle was doing what he loved, but he wasn’t getting the kind of exposure he needed to get to the next level.
It turned out, however, that that was just around the corner.
8. It Changed His Life
In 1992, Chappelle got a break that would change his life forever. Record executive Russell Simmons had a show called Def Comedy that appeared on HBO. The show was a way to showcase fresh, up-and-coming Black comedians. Chappelle was only 19 years of age—too young to even have a drink—when Simmons asked Chappelle to be on the show. Once the viewing public saw what Chappelle had to offer, they wanted more.
9. He Got A Name
Suddenly everyone seemed to want Dave Chappelle. David Letterman wanted him for his Late Show, and so did Conan O’Brian. Bill Maher was the host of Politically Incorrect and he thought Chappelle’s humor fit his show nicely. Howard Stern, whose radio show The Howard Stern Show had a reputation for being outrageous, also wanted Chappelle to appear. Chappelle was getting popular, so popular that Whoopi Goldberg gave him a nickname: “The Kid”.
While Goldberg’s nickname wasn’t all that clever, it was the beginning of something big for Chappelle.
10. He Goofed
When someone of Whoopi Goldberg’s status bothers to give you a nickname, something good has to come from it. Soon after he became The Kid, Chappelle got a role in Mel Brooks’ satire Robin Hood: Men In Tights. While Chappelle held his own against seasoned actors like Patrick Stewart and Tracey Ullman, audiences will likely remember him as being the one who messed up the choreography. During the title dance number, Chappelle lifts his right hand to his forehead and it was supposed to be the left—and then awkwardly tried to correct it.
Yes, he’d goofed up his first movie; next, he’d goof up on TV.
11. He Came In Second
Around this same time, Chappelle appeared in Star Search. Of course, Chappelle competed in the comedy genre of the reality show and he did it three times. In the end, Chappelle didn’t win. The winner was Lester Barrie. The surprise about Barrie was his day job: He was a Christian church pastor. Chappelle, however, didn’t need to worry about losing to a pastor, he had much bigger things coming his way.
12. He Said No
Back to the Future director Robert Zemeckis was looking for actors for a film he was making with Tom Hanks. No one was sure what the reception for Forrest Gump would be, but Chappelle seemed to have a bad feeling. When Chappelle read the script, he thought for sure that the film would be a failure, so he declined to play Bubba. Chappelle realized his mistake when Forrest Gump went on to win six Academy Awards. Chappelle shouldn’t feel too bad: Ice Cube also declined the role.
Chappelle’s career was off to a rocky start. What could he do to fix it?
13. He Made Fun
A few years later, Chappelle had apparently gotten over his near miss at superstardom. He made a short film that parodied Forrest Gump. In Bowl of Pork, Chappelle plays a man of low IQ that is responsible for some major moments in Black history. His character causes the beating of Rodney King, is responsible for the LA riots, and is even involved in OJ Simpson’s murder charge.
Chappelle was making light of a huge career blunder, but maybe it was time to get serious again about his career.
14. He Failed To Launch
Due to his popularity as a stand-up comic, Chappelle came to the attention of TV executives who wanted to capitalize on his fame. The usual route for a stand-up comic is to give them their own sitcom, ala Jerry Seinfeld. Producers made several pilots with Chappelle as the main character, but somehow none really took off. As a consolation prize, Chappelle got a guest spot on a fellow comedian’s show that did make it big: Tim Allen’s Home Improvement.
How would Chappelle stand up next to TV golden child Tim Allen?
15. They Were A Pair
When Chappelle appeared on Home Improvement, he acted opposite his real-life friend Jim Breuer. Something about the chemistry between these real-life friends struck a chord with audiences. Based on just one episode, Chappelle and Breuer received an offer for their own spinoff series, and that was how Buddies was born. Chappelle had finally found his way to his own show on TV. Unfortunately, things didn’t go as planned.
16. He Lost Him
Eight days before the television premiere of Buddies, Chappelle’s co-star—and friend—received a pink slip. For some unknown reason, the producers wanted him out, and they started looking for someone to replace him. This meant refilming all the episodes that were already done. It also meant that Chappelle wouldn’t be acting with his best bud. The replacement was Christopher Gartin, who had been in the superhero series MANTIS.
Chappelle didn’t care who his new co-star was: He wanted out.
17. He Got A Cash Offer
Chappelle had decided that he wouldn't do Buddies without his buddy, but getting out was going to be difficult. Chappelle’s agent said that he couldn’t break his contract with the studio. The producer of Buddies also wanted Chappelle to stay, so he made Chappelle an incredible offer. He said he would give Chappelle $10,000 if the show failed to be a hit.
Chappelle must have been torn. Which did he want: to score a hit TV show or get a big pile of cash?
18. He Was Owed
Buddies eventually premiered in March 1996, and the ratings...weren’t good. The studio ended up canceling it after airing only five episodes out of 13. It’s not clear if the producer ever followed up on his $10,000 offer, but he certainly should have. With the failure of Buddies, Chappelle had hit a low point and questioned whether show business was the right place for him. That’s when a new offer appeared—and it blew his mind.
19. He Got A Call
Remember, as a child Chappelle had been a huge fan of Eddie Murphy. Now Chappelle had received an offer to act with his idol in the comedy The Nutty Professor. The role wasn’t much of a stretch: Chappelle plays a stand-up comedian. Still, you can imagine that he was over the moon to be appearing in a film with his idol.
You can also imagine that he must have been more than a little nervous to meet and perform with Eddie Murphy. Well, he needn't have worried.
20. He Told Him
On his first day on set for The Nutty Professor, Chappelle was excited to meet Eddie Murphy. He had no idea, however, what kind of reception he would get from the huge star. When they finally got a chance to meet, Murphy told Chappelle that he liked his stand-up routine. It was a dream come true for Chappelle and it convinced him that he was doing the right thing with his life after some rocky years.
After this huge compliment from Murphy, Chappelle was ready to give TV another chance. But of course, the studios still weren't going to make it easy...
21. He Got A Call
Dave Chappelle was working on The Dave Chappelle Project when things went left with the studio. Fox wasn't too happy with the nearly all-Black cast that Chappelle proposed, so the comedian pulled the plug on the who thing. But that was just the beginning of a stroke of bad luck.
Around the time that Chappelle was dealing with his failing TV show, he got a tragic call from Ohio: His father had passed. Chappelle’s dad was only 59 when it happened, and it broke Chappelle’s heart. Chappelle returned to Ohio to bury his father, but it also gave him time to think. He again questioned whether show business was the right place for him. He was more than frustrated by the treatment he got from the studios.
That’s when Larry Sanders swooped in to help him get his revenge.
22. He Got Revenge
Chappelle was still hurting from his last pilot debacle where Fox wanted to replace Black actors with white ones. Chappelle then got a call to work on The Larry Sanders Show. This was a rare opportunity for an actor. In the episode "Pilots and Pens Lost," Chappelle gets to parody what happened to him on The Dave Chappelle Project. He got to tell Fox—in front of millions of viewers—exactly what he thought about their discriminatory behavior.
Still, The Dave Chappelle Project was another TV failure, and so Chappelle turned to the movies to show what he could do.
23. He Got A Chance
In 1998, Chappelle finally got a chance to show America what he was capable of: He was going to write and star in his own movie. Chappelle and comedian Neal Brennan wrote Half Baked and Chappelle quickly recruited his friend Jim Breuer—the one who’d been fired from Buddies—to appear. As you might have guessed from the title, Half Baked is a stoner comedy, which are generally panned by critics and loved by…well…stoners. Would this be any different?
24. It Was Overwhelming
Half Baked certainly lived up to its promise: Critics generally hated it. Its score on Metacritic translates into “overwhelming dislike”. However, the film ended up grossing over $17 million and has since become a cult classic. But behind the scenes, for all the references to being “baked,” there was only one incident where an actor actually was—and it almost derailed the entire movie.
25. He Wanted It Done Now
One of the great things about Half Baked is the cameo appearances. Audiences who remembered TV’s Mod Squad got the chance to see Clarence Williams III in Half Baked. One day on set, however, Williams became irate and wanted to shoot all his scenes in one day—that exact day! While the crew scrambled to get ready to do all of Williams’ scenes, Chappelle realized they had a problem: he’d already sent Williams’ scene partner Breuer home...with a bag of weed.
26. He Was Full On
When Chappelle called Breuer to return to the set, Breuer had already consumed the baggy full of treats. Apparently, Breuer had no choice but to do his scenes under the influence. Let’s just say, it took multiple takes to get his lines right as Breuer wasn’t only half baked, but likely fully. Incidents like this might have made Half Baked funnier, but even Chappelle later admitted that the final result of the film was not as funny as what he had envisioned.
While to some, Half Baked is a cult classic, to Chappelle it was just one more disappointment. What he needed was a big break, and it was just around the corner.
27. He Got A Second Chance
Chappelle had to recover from his half-hearted attempt to make people laugh in Half Baked. Remember, Chappelle had missed out on appearing with Tom Hanks in the wildly popular Forrest Gump. Well, Chappelle had a second chance, and he wasn’t going to mess it up. It turned out that Hanks needed a BFF for his character in the rom-com You’ve Got Mail. Chappelle got the offer, but it was for a surprising reason.
28. He Was In A Hit
Apparently, Tom Hanks remembered that Chappelle had missed out big time on Forrest Gump, and he’d promised himself that he would give Chappelle a second chance. Hanks convinced the casting people to hire Chappelle for You’ve Got Mail. Yes, this light comedy didn’t get the awards attention that Forrest Gump did, but it certainly made an impression. It was number one at the box office, and in the end grossed over $115 million dollars.
That's one way to put yourself on the map.
29. He Wouldn’t Do It
A year after appearing in the very white You’ve Got Mail, Chappelle got a chance to appear in a Martin Laurence film: Blue Streak. Everything was going great until the script called for Chappelle to do something he really didn’t want to do: put on a dress. Chappelle wanted the writers to rewrite the scene where his disguise is a female streetwalker. While this was a real drag for the writers, Chappelle had his reasons.
Chappelle said he found it a “disturbing trend” that Black actors wore dresses in films just for an easy laugh. But was that his only reason?
30. He Gave It Another Chance
After supporting roles in Screwed and Undercover Brother, Chappelle had an opportunity to give TV yet one more try. The result is Chappelle’s Show on Comedy Central. This was primarily a sketch comedy show that allowed Chappelle to do a brief stand-up performance before the sketches began. The show was immensely popular and Viacom—Comedy Central’s parent company—quickly greenlit a second season.
It seemed that Chappelle had finally found a place on TV. With Chappelle, however, things have a habit of going oh so wrong.
31. He Walked Off
One of the side projects that Chappelle decided to take part in was continuing his stand-up comedy routine. In 2004, Chappelle was up in front of a Sacramento, California audience when he noticed that some people in the crowd were chanting. When he realized what they were chanting about, Chappelle lost it and walked off the stage. So what was it that the audience wanted? They wanted Chappelle to quote catchphrases from his show.
He eventually went back on stage, but what he told the audience did nothing to help them forgive him for walking off.
32. He Called Them Names
In short, Chappelle called his audience stupid. He thought that any audience member who just wanted to hear catchphrases from his TV show lacked intelligence. He went on to say that this disappointed him because he’d always thought his fans were smart and got what he was doing. With this disappointment, things did not look good for season three of Chappelle’s Show.
33. He Needed Downtime
Chappelle had already made a few episodes of season three of his show, when he shocked fans and TV executives and walked off the job. It was only a few weeks before the season was about to air. Not only did Chappelle leave the show, he also left the country. Chappelle needed some downtime, and he thought he could find that in South Africa. Once he got there, he decided to let America know what was going on.
34. They Didn’t Believe Him
When Chappelle told Time magazine that he left Chappelle’s Show in search of balance in his life, the media jumped to some conclusions. Most tabloids saw his explanation as a cover-up, and they wanted to know the real reason Chappelle had quit. If he wasn’t going to tell them the truth, they’d make it up. Tabloids being tabloids, they went for the usual suspects: drug addiction or mental illness. Maybe giving up a $55 million contract did equal mental problems in some people’s eyes.
Chappelle had had it with the media and decided to lay low.
35. He Just Wants Respect
After Chappelle’s Show went sour, Chappelle seemed to cut back on his live performances. He did do a tour, but it seemed to be almost quiet in its marketing. When he spoke with Oprah Winfrey, he talked about his dissatisfaction with the entertainment industry. It seemed to all come back to his experience on Blue Streak where the writers asked him to put on a dress. Chappelle said that he felt the industry didn’t respect Black performers.
Sadly, Chappelle’s search for respect from the entertainment industry was about to take a serious hit.
36. He Made A Promise
There was some talk that Chappelle would return and finish the third season of Chappelle’s Show. He had one stipulation: that the network would never air material from the third season. The reason? Chappelle felt there was some stuff on there that he was not appropriate. In a shocking display of disrespect, Comedy Central did air those episodes, and Chappelle held to his promise: He would not return to the show.
37. He Was In For The Long Haul
In April 2007, comedian Dane Cook performed on the Laugh Factory stage for an astonishing three hours and 50 minutes, breaking Richard Pryor’s previous record. Well, we can only hope that Cook had a chance to celebrate his position as number one as it was short-lived. Just five days later, Chappelle slaughtered Cook’s record by giving a six-hour and seven-minute performance. Chappelle got to feel like number one for the rest of 2007. On January 1, 2008, however, Cook did a full seven hours.
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38. He Switched Places
Chappelle had already appeared on the interview show Inside the Actor’s Studio, but in 2008 he did a special version. It was the show’s 200th episode, so the creator of the show planned something strange. When the usual host, James Lipton appeared on stage with Chappelle, there was a switch: Chappelle interviewed Lipton, instead of the other way around.
39. He Cast the Blame
After a disastrous show in Hartford, Connecticut, Chappelle continued his tour with a performance in Chicago. While there, he let loose about how he felt about Hartford. He blamed young, white, inebriated audience members for the heckling. He said he would never stop in Hartford again—even for gas. He put the icing on the cake by saying that he hoped that North Korea would nuke the capital city of just over 120,000 people.
The next year, Chappelle got a standing ovation from a crowd in—you guessed it—Hartford Connecticut.
40. He Said They Were Weak
In 2018, Chappelle got called out for his on-stage comments about the #MeToo movement. He showed sympathy for canceled performers like Louis CK and Kevin Spacey. In a nutshell, Chappelle says that the victims were weak. He agreed that what the perpetrators did was wrong, but that the victims needed to just step it up a bit. Chappelle’s fan base didn’t seem bothered by this, but Chappelle was appearing on the radars of the woke generation.
Whatever Chappelle did next would be under close scrutiny.
41. They Should Feel Honored
In Chappelle’s Netflix special Sticks & Stones, the comedian was again in hot water. This time it was about Michael Jackson. In this special, Chappelle suggests that the childhood victims of Jackson’s alleged abuse were lying. He then changes tack and says that if the assaults did happen, the victims should feel honored because Jackson was the king of pop. Yikes!
Chappelle was taking potshots at just about anyone. But let’s see how he feels when the story is about him.
42. He Made A List
In 2020, controversial rapper Azealia Banks was compiling a list of influential people she’d slept with. A rather surprising addition to the list was Chappelle, whose marriage had seemed squeakily monogamous until this announcement. Some believe that Chappelle’s comment: “I’ll tell like Azealia Banks, I’ll tell” on his video 8:46 amounts to an admission of guilt. Others just don’t care.
What Chappelle said next, however, got his biggest and angriest response.
43. They Walked Out
On Closer—Chappelle’s sixth and final Netflix episode—Chappelle made some jokes at the expense of gay and transgender people that ruffled some feathers. Some Netflix employees were so angry that they took to the streets. They walked off the job to protest Chappelle’s appearance on their streaming service. Ted Sarandos—Netflix CEO—said that he didn’t think Chappelle’s comments were hate speech and refused to remove the show from the service. The Grammys didn’t seem to care either: Chappelle received his fourth Grammy for the album version of Closer.
Sure, maybe it wasn’t hate speech. But you have to wonder why Chappelle says the inflammatory things he says.
44. Don’t Tell Him No
Chappelle does try to explain the often controversial comments that he makes on stage. He says that when audiences or the media say he can’t talk about something, it means it’s even more important that he does talk about it. He says it’s not even that these controversial topics matter: instead, it’s just about the fact that he has the right to talk about anything he wants.
45. Someone Else Got Booed
Chappelle has received his fair share of audience hostility. In San Francisco’s Chase Center, however, Chappelle wasn’t the recipient. Chappelle was in the unenviable position of having to welcome the often unpopular Elon Musk to the stage. Musk had just purchased Twitter and had —some thought mercilessly—laid off a good chunk of its employees. So, when Chappelle introduced Musk as the richest man in the world, the crowd went ballistic. They booed for almost five minutes.
This was just a typical day at the office for Chappelle. Which makes me wonder what a typical day at home is like.
46. She Monitors
While Chappelle seems to live a wild existence on the stage, his home life is the exact opposite. He, his wife Elaine Chappelle, and their three kids live a quiet life on a ranch in Yellow Springs, Ohio. Elaine married Chappelle before he was famous, and she is completely devoted to him. She rarely gets involved in his public life, but does monitor the internet for reports about her famous husband. Elaine feels it’s her job to let Chappelle know when the negative publicity gets out of control. I think it’s safe to assume that these days that’s a full-time job.
47. He Came On Stage
Dave Chappelle will likely continue to get in trouble with critics and audiences. This next altercation, however, got a little too up close and personal. It was in May 2022, that Chappelle received something worse than heckling from an audience. Chappelle was performing at the Hollywood Bowl when a male audience member leaped up on the stage and tackled Chappelle. Security had no problem protecting the startled comedian, but what they found on the assailant was shocking: a fake pistol and a very real blade.
Chappelle certainly seems to have his ongoing problems with audiences, this next one, however, was about someone else.
48. They Wanted A Change
Remember when Chappelle parted ways with Fox studios? Well, here's how it all went down. Chappelle was in the middle of making the pilot for The Dave Chappelle Project, when the executives over at Fox got nervous. They weren’t sure if having a nearly all-Black cast was a good idea. They were wondering if Chappelle would be comfortable exchanging a few of the Black actors with white people. Chappelle made it clear that under no circumstances would he be happy with this. Chappelle went on to accuse the network of discrimination and then quit the show.
Chappelle had hit yet another low point. And then things just got worse.
49. He Had To Promise
Viacom was very pleased with Chappelle, and the popularity of Chappelle’s Show. They offered him a contract that seemed perfect: $55 million and the freedom to still pursue other projects. All Chappelle had to do was promise two more seasons. On paper, this sounds like a no-brainer. Yet, as we know, the success of Chappelle's Show led to a chaotic downfall for the controversial comedian.
50. They Drowned Him Out
Remember when Chappelle went off on the people in Hartford, Connecticut? Here's why he lost his cool. In 2013, Chappelle was in town and trying to do his number when members of the crowd started shouting. It was so loud that it was hard to hear Chappelle over the din. The crowd was yelling “white power”, which was a line from Chappelle’s Show. Chappelle refused to perform and eventually stormed off the stage. This, however, wasn’t over yet. The incident led to Chappelle blasting small town at his next performance.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17