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As Dave Chappelle faces backlash over a joke about the assassination of conservative activist Charlie Kirk, attention has turned to the comedian's history of controversial remarks.
Chappelle made the joke during a performance at Madison Square Garden, with footage of the comments circulating widely online.
He said: "Ever since that guy Charlie Kirk got murdered, and I shouldn't say this publicly, but I feel better."
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He went on to joke about finding himself in a good mood before remembering Kirk's death.
The remarks prompted widespread discussion online, including from several high profile figures, with Kirk's widow, Erika Kirk, criticizing people who make light of political assassination.
Newsweek reached out to representatives for Chappelle by email Sunday for further comment. When reached for comment on Sunday, TPUSA referred Newsweek to Erika Kirk's comments on X.
It is not the first time Chappelle has found himself in hot water. From jokes about transgender people and the LGBTQ community to his decision to walk away from his hit television show, the comedian has repeatedly divided audiences.
Here are some of the biggest controversies he has faced.
2005: Walking Away From Chappelle's Show
Chappelle shocked audiences in 2005 when he abruptly walked away from his hugely successful Comedy Central series, Chappelle's Show, despite being offered a reported $50 million deal.
He later explained that he had become uncomfortable with aspects of the show's success, including concerns that some viewers were laughing at, rather than understanding, the racial satire behind his sketches.
He also cited the pressures of fame and concerns about his creative control. His departure became one of the most talked-about moments of his career, with speculation surrounding his decision continuing for years.
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2017: Transgender Jokes Draw Criticism
Chappelle returned to the mainstream with a series of Netflix comedy specials in 2017, but his material attracted criticism over jokes about transgender people and gender identity.
He also addressed Rachel Dolezal, the former NAACP chapter president who became controversial after identifying as Black despite having white parents.
Chappelle drew comparisons between Dolezal's racial identity and transgender identity, prompting criticism from viewers who argued that the jokes were offensive and reinforced harmful stereotypes.
The material marked an early flashpoint in a debate over Chappelle's treatment of transgender issues, which would intensify following his later Netflix specials.
2019: Sticks & Stones Reignites LGBTQ Backlash
His 2019 Netflix special Sticks & Stones prompted further criticism over jokes about the LGBTQ community and wider celebrity scandals.
Chappelle also revisited material about R. Kelly amid renewed attention on allegations of sexual abuse against the singer.
While some viewers defended the comedian's right to tackle controversial subjects, others accused him of dismissing legitimate concerns and making light of serious issues.
2019-2021: The Daphne Dorman Controversy
Chappelle's friendship with transgender comedian Daphne Dorman also became a source of controversy.
Dorman, who died by suicide in 2019, had publicly defended Chappelle against accusations that his jokes about transgender people were hateful.
The comedian subsequently discussed their friendship in his routines, using her support to explain his perspective on the transgender community.
However, critics questioned his use of Dorman's story, particularly as tensions surrounding his material continued to grow.
October 2021: The Closer Sparks Major Backlash
One of the biggest controversies of Chappelle's career came with the release of his Netflix special The Closer in October 2021.
During the show, he declared himself "Team TERF," defended author J.K. Rowling and made a series of jokes and comments about transgender people, sex and gender identity also referring to himself as "transphobic."
LGBTQ organizations and activists condemned the special, accusing Chappelle of making transphobic remarks and reinforcing harmful stereotypes.
The comedian stood by his material, while Netflix defended its decision to keep the special available on the platform.
October 2021: Netflix Employees Stage Walkout
The controversy escalated into an internal dispute at Netflix, with employees and activists staging a walkout in October 2021.
Hundreds of people took part in the protest, objecting to the streaming company's handling of The Closer and calling for greater consideration of transgender employees and viewers.
Netflix co-CEO Ted Sarandos defended the company's decision to release the special, although he later acknowledged that he had mishandled communications with staff.
November 2022: Saturday Night Live Antisemitism Row
Chappelle faced another backlash in November 2022 after hosting Saturday Night Live.
His opening monologue addressed antisemitism following controversial remarks made by rapper Kanye West, now known as Ye.
Although Chappelle condemned antisemitism, critics argued that parts of his routine invoked stereotypes about Jewish influence in Hollywood.
The comments prompted criticism from Jewish organizations, including the American Jewish Committee, which said elements of the monologue risked reinforcing antisemitic ideas.
Chappelle's comments on Israel and Gaza later drew further attention. While he reportedly condemned the October 7, 2023, Hamas attack on Israel, he also criticized Israel's military response in Gaza, describing the situation as "genocide" during a 2024 performance.
November 2026: Charlie Kirk Joke Sparks Fresh Backlash
Chappelle's comments about Kirk's death drew criticism from several high-profile figures.
Billionaire Elon Musk condemned the joke in a post on X, writing: "Shame, shame, shame on Chappelle." Broadcaster Piers Morgan also criticized the remarks, describing them as "disgusting."
Other commentators, including Meghan McCain and Benny Johnson, spoke out against the comedian, with Johnson posting: "When Dave Chappelle was attacked on stage, Charlie stood up for him," referring to an incident in May 2022, when a man rushed the stage and attacked Chappelle during a performance at the Hollywood Bowl in Los Angeles.
Kirk’s widow, Erika Kirk, subsequently criticized those who laughed about political assassination, although she did not name Chappelle directly.
She wrote: "To see leftist podcasters, comedians, and commentators laugh about political assassination as though it's entertainment and the destruction of a human life is a punchline, is beyond disgusting."
She added that people did not have to agree with someone's politics to recognize the value of their life.
Contact Newsweek editors for this story: Robert Greenall and John Fitzpatrick
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