What Most People Don't Know About Dave Chappelle

Dave Chappelle was still in high school when he began following his dream of becoming a standup comic. According to Biography, the young comedian moved to New York City right after graduation and soon began making a name for himself; Chappelle was just 19 when he landed a role in Mel Brooks' 1993 comedy Robin Hood: Men in Tights. A few short year later, he was starring in his own TV sitcom — and while it didn't last long, Chappelle had successfully established himself as a comedic force to be reckoned with.

It wasn't until the early 2000s, however, that he really hit the heights when his Comedy Central sketch series Chappelle's Show made home-video history when, as Entertainment Weekly reported in 2005, the second season became the fastest-selling TV-on-DVD release ever. At the peak of his success, with Comedy Central offering a hefty chunk of change for two more seasons, Chappelle abruptly quit, disappearing and laying low for years until eventually re-emerging, sharper and funnier than ever. 

All of that is only part of Chappelle's story; there is always more about him that fans can discover. Keep on reading to find out what most people don't know about Dave Chappelle. 

A brief cameo on a hit TV show nearly propelled Dave Chappelle to TV stardom. When Chappelle and fellow comedian Jim Breuer appeared in a 1995 episode of Home Improvement, it set some wheels in motion. Despite the brevity of the guest spot, their comedy chemistry attracted the attention of ABC executives, who signed the duo for a spinoff, titled Buddies.

In public, the duo exuded confidence that Buddies would be a hit, with Breuer joking to the Los Angeles Times that "we're gonna knock Home Improvement on its..." Yet, as Vulture recalled, those same network execs became less impressed while the pilot was being filmed, worrying that Breuer's scenery-chewing style would take over every scene. Breuer was fired, replaced by actor Christopher Gartin. Don't feel too bad for Breuer; shortly after receiving his pink slip, he was hired for the cast of Saturday Night Live. And when the retooled Buddies finally made its TV debut in 1996, it was met with a collective "meh" from viewers, and axed after only five episodes aired.

It took a couple of years, but Chappelle and Breuer eventually did work together, co-starring in the 1998 stoner classic Half Baked.

Listed by Time as one of the top 10 most reclusive celebrities, Dave Chappelle doesn't live in Beverly Hills or New York's Upper West Side, but in a farm outside the small town of Yellow Springs, Ohio. 

In an interview with Hot 97's Ebro in the Morning, Chappelle explained how he landed in rural Ohio. He moved there, he revealed, "because my parents split up when I was a kid and my dad had lived out there. He got real sick in like '98, so I would drive back and forth from New York. And there's no good hotels where I live, so I just bought a house. Then, at a certain point, I just moved into the house. Then, when I quit [Chappelle's Show], I moved back into the house."

According to Chappelle, he could easily afford to live in the Big Apple if he wanted to. "But I would have to work all the time," he explained. "But in Ohio, I can do that for a long time and not work. As far as people out there know, I don't work. They never see me work."

Standup comedy pretty much demands a live audience, which became a huge issue in March 2020 when the global pandemic shut down live performances. That summer, however, Dave Chappelle came up with an idea that would allow him and some of his fellow comics to perform safely, in front of a socially distanced audience of just 100 at an outdoor venue in his hometown of Yellow Springs, Ohio, about a half-hour outside of Dayton. 

According to Cleveland.com, the people who attended the shows at Yellow Springs' outdoor Wirrig Pavilion received temperature checks before entering and were required to wear face masks.

Thanks to Chappelle, those lucky few who attended the shows enjoyed some world-class live entertainment during a time when live entertainment was more or less shut down. As the Springfield News-Sun reported, Chappelle's shows attracted such talent as John Mayer, Sarah Silverman, Tiffany Haddish, Common, David Letterman, Jon Stewart, Chris Rock, Jon Hamm, Michael Che, Erykah Badu, Michelle Wolf, and Trevor Noah, among others. "This weekend was a memory I'll cherish for the rest of my life," Daily Show host Noah wrote of the experience on Facebook. "I've never had more fun performing outdoors!"

During a 2009 standup set, Dave Chappelle revealed that he once worked at the theater where President Abraham Lincoln was assassinated by John Wilkes Booth. "I had nothing to do with the murder," Chappelle joked to the audience. 

He elaborated on that job, which he held while he was in high school, during an interview with NPR's What's Good With Stretch And Bobbito podcast. "I used to be an usher at Ford's Theatre, where Lincoln got shot," he said, but explained that he didn't remain employed there for too long. "I quit like Chappelle's Show. I just stopped going," he said.

According to Chappelle, once he made his abrupt exit he never returned. "And then the guy who called me up, he was like, 'Yo, Dave, do you want to come get your check?' And I'm like, 'Yeah, I'm not falling for that,'" he cracked.

Dave Chappelle is known as a comedian's comedian, arguably one of the best that is and ever was on a standup stage. In October 2019, he was formally recognized for his comedy abilities when he was awarded comedy's most prestigious honor, the Mark Twain Prize for American Humor, at the posh John F. Kennedy Center for the Performing Arts in Washington, DC. Chappelle is in some pretty rarified company; past winners include the likes of Carol Burnett, David Letterman, George Carlin and inaugural Mark Twin Prize recipient Richard Pryor.

"Dave is the embodiment of Mark Twain's observation that 'against the assault of humor, nothing can stand,'" said Deborah F. Rutter, president of the Kennedy Center, in a statement to NPR. "For three decades, Dave has challenged us to see hot-button issues from his entirely original yet relatable perspective."

In his acceptance speech, Chappelle paid tribute to standup comedy itself. "There is something so true about this genre, when done correctly, that I will fight anybody that gets in a true practitioner of this art form's way," he told the Kennedy Center audience while puffing a cigarette, "because I know you're wrong."

Forrest Gump is one of Hollywood's most beloved movies, sweeping the 1995 Oscars by winning a whopping six Academy Awards. Dave Chappelle could have been a part of this historic film — but turned it down. According to IMDb and TV Overmind, the role of Forrest's Vietnam War buddy, shrimp-obsessed Benjamin Buford "Bubba" Blue, went to Mykelti Williamson after several other actors passed, including Ice Cube and Chappelle. After reading the script, Chappelle apparently surmised Forrest Gump would be a box-office bomb. So, he didn't take the part.

When he subsequently had the opportunity to work with Tom Hanks again, Chappelle jumped at it; he played Hanks' sidekick, Kevin, in the 1998 rom-com You've Got Mail, although that movie was nowhere near as big a hit as Forrest Gump.

Chappelle referenced Forrest Gump during a 1999 appearance on The Daily Show, possibly offering insight into why he turned down the role. He joked to then-host Jon Stewart that he became "mad" watching the film. "This guy is doing more by accident than I can do on purpose," he continued. "And I start getting furious. Who can be dumber than Forrest Gump? His Black friend, that's who."

The success of Chappelle's Show catapulted Dave Chappelle to a whole new level, playing to larger venues than he ever had before. As a result, these shows took on an aura more associated with a rock concert than a comedy show.

That ultimately proved frustrating to Chappelle, who boiled over at a Sacramento show in 2004 when some of the rowdier members of the audience insisted on shouting out his Chappelle's Show catchphrases. As the Sacramento Bee reported (via Mic), the exasperated comic told the crowd, "The show is ruining my life." Standup comedy, he said, is "the most important thing I do, and because I'm on TV, you make it hard for me to do it."

He admonished the crowd, telling them, "This ain't a TV show. You're not watching Comedy Central. I'm real up here talking." When the audience still wouldn't quiet down, he reportedly left the stage for two minutes, only to return to tell the audience why they liked Chappelle's Show. "Because it's good," he said. "You know why my show is good? Because the network officials say you're not smart enough to get what I'm doing, and every day I fight for you. I tell them how smart you are. Turns out, I was wrong. You people are stupid."

The success of Chappelle's Show cannot be understated, breaking DVD sales records and generating big money for Comedy Central. In 2004, The Hollywood Reporter (via Today) reported Dave Chappelle was offered a $50 million deal for two more seasons. However, Chappelle instead simply bowed out, fleeing to South Africa amidst unfounded rumors of drug abuse and mental instability. 

Why Chappelle chose not to continue the show is complicated. As he explained to Time in 2005, he made the decision while shooting a sketch in which he played pixie who was in blackface. In 2006, he told Oprah Winfrey that the sketch had a "good-spirited intention behind it," but while filming, "somebody on the set [who] was white laughed in such a way — I know the difference of people laughing with me and people laughing at me — and it was the first time I had ever gotten a laugh that I was uncomfortable with." Once he started to feel "socially irresponsible," he walked away. 

Years later, he joked about his exit with David Letterman on The Late Show. "I never quit," he said (via Rolling Stone). "I'm seven years late for work."

In 2019, singer R. Kelly was arrested on federal charges of sex trafficking. That same year, Lifetime released Surviving R. Kelly, the disturbing docuseries in which numerous women shared their allegations of sexual abuse at Kelly's hands. As of November 2020, Kelly is in jail and waiting for trial. As the Chicago Tribune reported, he has pleaded not guilty to all charges.

Many years before his 2019 arrest, rumors abounded regarding Kelly and an explicit video  — which Dave Chappelle spoofed in a sketch for Chappelle's Show. The singer was reportedly not pleased with Chappelle's mock music video. According to TMZ, Chappelle was onstage in West Hollywood performing a standup set when he recalled being confronted by Kelly's "goons" while attending a Common concert in Chicago. Joked Chappelle, "I don't know if it was his goons, but they sure did like him." 

Comedian Neal Brennan, co-creator of Chappelle's Show, confirmed the story during a subsequent interview with The Breakfast Club radio show. "R. Kelly wanted to fight Dave," said Brennan, explaining what took place and why the situation never escalated. "His goons stepped to Dave in Chicago ― and Dave's goons intervened, and the goons negotiated." In 2016, Kelly told GQ he had not seen the Chappelle's Show sketch.

Not all of Dave Chappelle's public proclamations take place during his standup comedy routines. In 2017, he spoke out at a city council meeting in his hometown of Yellow Springs, Ohio, discussing an incident on New Year's Eve that left residents feeling police had overstepped their bounds by using Tasers on citizens. One resident told The New York Times, "I don't know if I would call it a coincidence that out of a majority white crowd, a Black man would be the one to get tackled to the ground and Tased."

Describing what took place as a "huge gaffe," Chappelle insisted he also saw the situation as an "opportunity to be a leader in progressive law enforcement."

Discussing the resignation of the town's police chief in the wake of the incident, Chappelle implored the council members that when hiring a new police chief they needed to "look deeply and look hard" for the right person to represent their "incredibly unique" town. "This is a golden opportunity — literally, could kill the game," Chappelle said. "In this Trump era, there's an opportunity to show everyone that local politics reigns supreme. We can make our corner of the world our standard."

Dave Chappelle sees the comedy world as his domain, so it shouldn't be surprising that his closest friends are his fellow comedians. One of these friends is Chris Rock. Regarding their friendship, Rock told Howard Stern in September 2020 that he's "just in love with Dave" and called their dynamic a "Basquiat/Warhol thing."

In fact, Chappelle made an unannounced appearance at Rock's 2017 performance in New Orleans. According to the New Orleans Advocate, fans at the show were shocked when, instead of Rock, it was Chappelle who took to the stage, performing for about 20 minutes before he was joined by the scheduled headliner. As Chappelle joked to the audience, they were attempting "a social experiment. Chris Rock is in Austin headlining my show... What we're trying to figure out is: Does it really make a difference?"

If their joint appearance was indeed an "experiment," it's one that can be deemed a success, judging by the Advocate's reporting of the crowd's delighted response. At the end of the show, Chappelle quipped, "I just realized this might be one of the flyest things I've ever been a part of. The only thing better would be if Eddie Murphy lowered from the rafters."