Dave Chapelle’s Net Worth Comes With a Serious Side of Controversy

Dave Chapelle's $60 million net worth was built on a lot of controversial jokes, and only time will tell how it affects the comedian's career.

Comedian Dave Chapelle is best known for his satirical sketch show “Chappelle’s Show” and has received numerous accolades, including several Emmy Awards and the Mark Twain Prize. With a net worth of $60 million, he’s very much an American success story, but that story has also been plagued by controversy.

While Chapelle has always been a controversial comedian, his 2021 Netflix special, “The Closer,” made several jokes at the expense of the transgender community, sparking an immense amount of backlash in the months that followed. The special recently earned an Emmy Award nomination, bringing the drama surrounding the comedian back into the spotlight.

To say he’s been canceled for being transphobic would be an understatement, but there are still several fans who love Chappelle’s work — so much so that the show in question had nearly 400 million streamed minutes in its first week airing on Netflix. In fact, he’s an interesting study in how cancel culture can affect someone’s career, and only time will tell what kind of damage it does (if any) for Chappelle.

Take a look at the history of his career to see what led him to this point.

Funny From an Early Age

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David Khari Webber Chappelle was born on Aug. 24, 1973, in Washington, D.C. He started pursuing a stand-up career when he was still in high school, inspired by the popular sitcom “The Cosby Show.”

Chappelle’s mother was his biggest supporter, chaperoning him to comedy clubs when he was still underage.

One of America’s Funniest (and Most Controversial)

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Chapelle is certainly not new to controversy. In September 1990, the comedian was featured in a montage of random people telling jokes in the first episode of ABC’s “America’s Funniest People.”

Around this time, he moved to New York City to try to become a professional comedian. From the start, he didn’t shy away from offensive content. In fact, he was booed offstage during amateur night at New York’s famous Apollo Theatre.

TV Acclaim

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Chappelle received critical acclaim for his 1992 appearance on Russell Simmons’ “Def Comedy Jam” on HBO. It was a hit with viewers, too, and ultimately led to regular guest slots on shows like “The Late Show With David Letterman” and “Late Night With Conan O’Brien.”

Whoopi Goldberg was impressed, giving Chappelle the nickname “the Kid”.

Breaking Into Films

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Chappelle’s movie career started with the role of Ahchoo in Mel Brooks’ “Robin Hood: Men in Tights” in 1993. It was a spoof of “Robin Hood: Prince of Thieves,” and Achoo was based on Morgan Freeman’s character Azeem.

Of discovering Chappelle, Brooks told GQ, “[He] was so unassuming, so sweet, as well as funny. I said, ‘That’s the guy.’”

‘Star Search’ Failure

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Also in 1993, Chappelle appeared on several episodes of “Star Search” but ultimately lost to fellow comedian Lester Barrie. However, it didn’t do Chappelle any harm.

In 2014, looking back on his early career flops, he told GQ, “I’m a slow learner. Early in my career, I was along for a ride. And then, later in my career, I was like, ‘You know, I should really drive. ’Cause nobody has ever taken me to a place I actually want to go.’”

Opening for Aretha

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At the tender age of 19, Chappelle was the opening act for R&B soul singer Aretha Franklin at Radio City Music Hall. In 2014, he told Rolling Stone that he was sure Franklin didn’t choose him herself. “It was 15 minutes. I had about 30 minutes [of material] then — I was prepared enough,” he said. “Was I as good as Aretha Franklin? Nah. But my job was just to get people used to looking at the stage.”

He added that he “skipped the soundcheck, and nobody could hear [me] for the first three minutes.”

Turning Down ‘Forrest Gump’

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Chappelle landed the role of Benjamin Buford “Bubba” Blue in “Forrest Gump,” which was released in 1994, but he turned it down because he believed that the character was demeaning and the movie would flop.

As we all know, it went on to be one of the biggest U.S. box office successes of its day. Still, 1994 was a good year for Chappelle — he became the youngest comedian to be featured on the HBO special “Comic Relief VI.”

On the Pilot Circuit

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Chappelle played another supporting role in the film, “Getting In,” in 1994. Around this time, he was on the radar of various TV network executives.

Although numerous pilots were created, none were picked up for development into a series.

Making an Impact on ‘Home Improvement’

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In 1995, Chappelle made a guest appearance on an episode of ABC’s popular sitcom “Home Improvement.” He appeared alongside his real-life friend, fellow comedian Jim Breuer.

Their characters asked Tim Taylor for advice on their girlfriends, and they were so popular that they got their own spinoff sitcom with the network.

Short-Lived ‘Buddies’

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The “Home Improvement” spinoff was titled “Buddies,” and it focused on Chappelle’s and Breuer’s characters and their lives in New York City. After the pilot was filmed, Breuer was fired and replaced with actor Christopher Gartin.

Unfortunately, the show didn’t live up to expectations and was canceled after just four episodes due to low ratings. Even Chappelle admitted, “It was a bad show. It was bad. I mean when we were doing it, I could tell this was not gonna work.”

A Hollywood Regular

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More roles in high-profile movies came Chappelle’s way in the mid- to late-90s, including “The Nutty Professor” (1996) with Eddie Murphy, who happened to be one of Chappelle’s major influences.

He also had a minor role in “Con Air” (1997) with Nicholas Cage and “You’ve Got Mail” (1998) with Tom Hanks and Meg Ryan.

Personal Tragedy

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Despite the failure of “Buddies,” Chappelle decided to star in another pilot. According to Chappelle, the network wanted to add white actors because it was uncomfortable with the amount of African American cast members. Chappelle accused the network of racism.

Shortly afterward, the comedian’s father died, and he considered leaving the entertainment business altogether.

A Leading Role

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Chappelle’s first lead movie role was in “Half Baked,” a 1998 stoner comedy film he co-wrote with Neal Brennan. Chappelle co-starred with Guillermo Díaz and Jim Breuer, playing a janitor named Thurgood Jenkins who likes to smoke weed and a rapper named Sir Smoke-Lot.

According to Mental Floss, Chappelle was inspired to write the script after learning about New York City drug dealers who deliver illicit substances to their customers’ apartments.

He and Neal Brennan co-wrote the film, which became Chappelle’s first starring role about a group of weed-smoking friends trying to get their other friend out of jail. It now has a bit of a cult following and is seen as a classic “stoner” movie.

Still Searching for the Game Changer

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Chappelle continued to make movies, including “Blue Streak” (1999) and “Undercover Brother” (2002). In 2000, he filmed a hugely popular comedy special “Killin’ Them Softly” at the Lincoln Theatre in Washington, D.C.

Covering police, politics and race relations, it was Chappelle’s first hour-long HBO special and helped grow his fanbase.

‘Chappelle’s Show’

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Chappelle teamed up with Neal Brennan again on the Comedy Central sketch show “Chappelle’s Show.” From 2003 to 2006, it offered viewers plenty of satire. Chappelle also executive-produced the show, alongside Brennan and Michele Armour.

In the middle of production of the third season, Chappelle abruptly quit the show and went back to performing stand-up across the U.S.

America’s Comic Genius

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In 2006, Chappelle was called “the comic genius of America” by Esquire. During the interview, he shed some light on why he’d left TV and gone back to his stand-up roots.

“People are thinking that I’m out here to avoid fame, and that’s not it. What I’m trying to avoid is corruption,” he said, adding that things were “starting to make more sense, like a fog that’s lifting.”

Rolling Stone Ranking

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Rolling Stone ranked Chappelle No. 9 in their “50 Best Stand Up Comics of All Time” in 2017.

“Dave Chappelle has not only reasserted himself in the game but put himself right back on top,” wrote the publication, adding that he “relishes the fuzzy line between truth and fiction, and delights in keeping the audience on the hook until they’re scratching their heads.”

First Emmy Award

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Chappelle received his first Emmy Award in 2017 for his guest appearance on “Saturday Night Live.”

Not surprising at all, it was a controversial episode, and Chappelle later apologized for telling viewers they should give Donald Trump a chance — but not for the language that prompted North Carolina NBC affiliate WRAL-TV to bleep him repeatedly.

Multimillion-Dollar Netflix Deal

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In 2016, Chappelle signed a comedy-special deal with Netflix to the tune of about $60 million for four stand-up specials, including “Equanimity,” “The Bird Revelation,” “Sticks and Stones” and “The Closer.”

“Equanimity” was nominated in 2018 for three Emmys and received the award for Outstanding Variety Special (Pre-Recorded). “Sticks and Stones” also won an Emmy in 2020, and the previously mentioned “The Closer” was nominated for an Emmy Award in 2022.

Grammy Success

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A particularly good year for Chapelle was 2018. He appeared in “A Star Is Born” as Jackson Maine’s longtime friend, George ‘Noodles’ Stone. According to Vulture, Chappelle agreed to come on board after director Bradley Cooper, who played Maine, turned up at Chappelle’s annual barn party, then phoned him every two days to convince him.

In 2018, Chapelle also received a Grammy Award for his Netflix-produced comedy album “The Age of Spin and Deep in the Heart of Texas”.

The Highest Comedy Honor

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The Mark Twain Prize for American Humor, which is presented by the Kennedy Center as America’s highest comedy honor, was presented to Chappelle in 2019.

This prize is awarded to people who have “had an impact on American society in ways similar to” Twain. Before receiving the award, Chappelle told NPR that stand-up, which he considers to be “an American phenomenon,” is his “favorite mode of expression.”

Credit to His Influences

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When he accepted his Mark Twain Prize, Chappelle acknowledged three important people: comedian Tony Woods, director Stan Lathan and his mother.

“But early in my career, if you remember, Mom, you used to sit in the club with me,” Chappelle said. “She’d do a full day of work. You’d be back there falling asleep, just waiting for me to go on. She would watch my show every night. Do you know how long that car ride is home?”

A Return to ‘Saturday Night Live’

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Chappelle hosted “Saturday Night Live” after the 2020 presidential election, despite being reluctant to return. In a video shared to the SNL Twitter page, he said, “I saw so much press about what’s happening in the country and the way people [have] been feeling. And I’ve been watching the show recently. When I said — at the read-through, I sincerely meant there’s something really beautiful about this kind of effort in the face of this kind of turmoil.”

He added, “This is how we fight; this is how we protest; this is how we celebrate this genre of comedy. It’s our job, and every once in a while we’re lucky enough to be in a context where our job is to mean something more than just being funny.”

Calling for a Boycott

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In 2020, Chappelle had a strange request for his fans — not to stream his show. “I’m begging you. If you ever liked me,” he said in a video of a stand-up routine he shared on Instagram. “Boycott ‘Chappelle’s Show.’ Do not watch it unless they pay me.”

He was calling out Comedy Central, which first aired “Chappelle’s Show” from 2003 to 2006 and licensed it to Netflix and HBO Max without telling Chappelle about the deal or paying him any money.

As Chappelle explained, Comedy Central was able to do this because he’d been trapped in an unfair contract when he was a young performer.

Thanking Fans

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Chappelle’s bold strategy paid off. He later revealed that Comedy Central had given him back the rights to his name and likeness along with “millions of dollars.”

“I asked you to stop watching the show, and thank God almighty for you, you did. You made that show worthless because without your eyes it’s nothing. And when you stopped watching it, they called me,” he said, as reported by The New York Times. “And I got my name back, and I got my license back, and I got my show back, and they paid me millions of dollars. Thank you very much.”

Turning His Hand to Podcasting

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In 2021, Chappelle launched a new podcast with Talib Kweli and Yasiin Bey called “The Midnight Miracle.” According to a press release, the “salon style” show would provide “a glimpse into a very interesting season in the lives of the three hosts and their friends, and features guests from among the country’s most influential cultural icons.”

Chappelle revealed, “Making a podcast isn’t the obvious next move for me, but it’s the right one. ‘The Midnight Miracle’ gives you a look into how me and my friends process the world around us, and I think it will change the way listeners think of what a podcast can be.”

Protecting His Private Life

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Chappelle has always made it a priority to keep his family out of the public eye, and part of that was choosing to set up a home in rural Ohio. Chapelle, his wife Elaine and three children live on a 65-acre farm property in the town of Yellow Springs.

During a 2017 interview with David Letterman, Chappelle revealed how much his family has influenced both his career and his character. “Everything changed after I had children,” he said. “I took my professional life more seriously. And I think, as a dude, I had more depth after I had kids.”

Courting Controversy

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Alongside serious takes on pressing social issues, Chappelle relies on plenty of raunchy jokes to entertain the masses. And he’s not afraid to take the heat.

He famously said he didn’t believe Michael Jackson’s accusers and continues to make jokes about transgender people — the latter of which caused an employee walkout at Netflix in the fall of 2021.

Even his former high school, which was contemplating naming the school theater after him, opted to pause the decision due to the backlash.

More Netflix Specials to Come

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But it appears Netflix isn’t afraid of a little controversy, as the company teamed up with the comedian again in 2022 for “Chappelle’s Home Team,” a series of four comedy specials with Chappelle as executive producer.

While several Netflix employees were upset about the decision, Ted Sarandos, the company’s co-CEO and chief content officer, told the Wall Street Journal, “We have articulated to our employees that there are going to be things you don’t like. There are going to be things that you might feel are harmful. But we are trying to entertain a world with varying tastes and varying sensibilities and various beliefs, and I think this special was consistent with that.”

In the meantime, Chapelle has said he’s open to talking more with the LGBTQ community about the insensitive jokes, but it seems they’re still waiting for that to happen.