1990–2002: Early career and breakthrough Chappelle was featured in a montage of random people telling jokes in the first episode of
ABC's ''
America's Funniest People'', airing on September 13, 1990. Following his high school graduation, Chappelle moved to
New York City to pursue a career as a comedian. He performed at
Harlem's
Apollo Theater in front of the "Amateur Night" audience, but he was
booed off stage. Chappelle described the experience as the moment that gave him the courage to continue his show business aspirations. In 1992, he won critical and popular acclaim for his television appearance in
Russell Simmons'
Def Comedy Jam on
HBO. It was his appearance on this show that allowed his popularity to truly begin rising, eventually allowing him to become a regular guest on late-night television shows such as
Politically Incorrect,
Late Show with David Letterman,
The Howard Stern Show, and ''
Late Night with Conan O'Brien. Whoopi Goldberg nicknamed him "The Kid". He parodied the film in the 1997 short Bowl of Pork'', where a dim-witted black man is responsible for the
Rodney King beating, the
LA riots and
O. J. Simpson's being accused of murder. Chappelle played another supporting role in an early
Doug Liman film,
Getting In, in 1994. At age 19, he was the opening act for R&B soul singer
Aretha Franklin. Chappelle attracted the attention of television network executives and developed numerous
pilots but none were picked up for development into a series. In 1995, he made a guest appearance on an episode of ABC's popular
sitcom Home Improvement. The storyline had Chappelle and real-life friend and comedian
Jim Breuer ask
Tim Taylor for advice on their girlfriends. The characters' single outing in the episode proved so popular that ABC decided to give them their own
spin-off sitcom titled
Buddies. However, after taping a pilot episode, Breuer was fired and replaced with actor
Christopher Gartin.
Buddies premiered in March 1996 to disappointing
ratings and the show was canceled after only five episodes out of 13 that had been produced. After the failure of
Buddies, Chappelle starred in another pilot. According to Chappelle, the network was uncomfortable with the
African-American cast and wanted
white actors added. Chappelle resisted and subsequently accused the network of racism. Shortly afterward Chappelle's father died and, after returning to Ohio, he considered leaving the entertainment business. He had a minor role in 1997's
Con Air. At the beginning of 1998, he did a stand-up performance for
HBO Comedy Half-Hour. That same year, he appeared in "Pilots and Pens Lost", an episode of
The Larry Sanders Shows sixth season, in which he and the executives of the show's unnamed
television network satirize the treatment that scriptwriters and show creators were subjected to, as well as the executives' knee-jerk tendencies toward
racial stereotypes. He and
Neal Brennan co-wrote the 1998 cult
stoner film Half Baked, Chappelle's first starring role, about a group of
marijuana-smoking friends trying to get their other friend out of jail. It made money at the box office and remains a classic "stoner" film, a genre that includes the
Cheech & Chong films as well as more recent fare like
Judd Apatow's
Pineapple Express. In December 1998, Chappelle appeared as
Tom Hanks' character's friend and confidant in ''
You've Got Mail. In 1999, he appeared in the Martin Lawrence film Blue Streak''. In 2000, Chappelle recorded his first hour-long
HBO special, ''
Dave Chappelle: Killin' Them Softly, in Washington, D.C. He also starred alongside Norm Macdonald in the 2000 comedy film Screwed. He followed this with an appearance as "Conspiracy Brother" in the 2002 racial satire Undercover Brother''. During the early 2000s, Chappelle was a member of the
Spitkicker artist collective, along with many
hip-hop artists like
De La Soul and
Talib Kweli.
2003–2006: ''Chappelle's Show'' In 2003, Chappelle debuted his own weekly
sketch comedy show on
Comedy Central called ''
Chappelle's Show''. The show parodied many aspects of American culture, including
racial stereotypes, politics and
pop culture. Along with comedy sketches, the show also featured musical performances by mostly
hip-hop and
soul artists. He promoted the work of other black comedians as well, most notably
Paul Mooney and
Charlie Murphy. James' estate disagreed with the proposed comical tone of the film and put a halt to the talks. That same month, Chappelle recorded his second comedy special, which aired on
Showtime, ''Dave Chappelle: For What It's Worth'', at
San Francisco's
Fillmore Auditorium, where
Lenny Bruce,
George Carlin,
Richard Pryor, and
Robin Williams had performed.
Season 3 problems Season 3 was scheduled to begin airing on May 31, 2005, but earlier in May, Chappelle surprised fans and the entertainment industry when he abruptly left during production and took a trip to
South Africa. Chappelle said on
Inside the Actors Studio that the death of his father seven years prior influenced his decision to go to South Africa. By throwing himself into his work, he had not taken a chance to mourn his father's death. He also said the rumors that he was on drug or psychiatric treatment only persuaded him to stay in South Africa. He did not rule out returning to ''Chappelle's Show
to "finish what we started", but promised that he would not return without changes to the production. Chappelle expressed disdain at the possibility of his material from the unfinished third season being aired, stating that to do so would be "a bully move", and that he would not return to the show if Comedy Central were to air the unfinished material. On July 9, 2006, Comedy Central aired the first episode of Chappelle's Show: The Lost Episodes. After the DVD release, Chappelle was interviewed by Anderson Cooper on CNN and reiterated he would not return to Chappelle's Show''. Chappelle's abrupt departure from the show continues to be a focus of interviews and profiles of him and of his own comedy. His decision to quit the show meant walking away from a $50 million contract with Comedy Central In
Bird Revelation, Chappelle draws an analogy between his departure and the book
Pimp, the memoir of
Iceberg Slim.
2004: ''Dave Chappelle's Block Party'' in
Brooklyn on May 16, 2007, which was the site of the documentary ''
Dave Chappelle's Block Party'' (2005) Chappelle was the star and a
producer of the
Michel Gondry-directed documentary ''
Dave Chappelle's Block Party'', which chronicles his hosting a free concert in the
Clinton Hill neighborhood of
Brooklyn on September 18, 2004. Chappelle toured several cities in February and March 2006 to promote the film under the name "Block Party All-Stars Featuring Dave Chappelle".
Universal Pictures' genre division,
Rogue Pictures, released the film in the U.S. on March 3, 2006. It was a success, grossing a total of $11.7 million on a $3 million budget.
2005–2015: Infrequent comedy appearances Chappelle has been known to make impromptu and unannounced appearances at comedy venues, and continued to do so following his post–''Chappelle's Show'' return to stand-up comedy. In June 2005, Chappelle performed impromptu stand-up shows in Los Angeles, then went on a tour that began in
Newport, Kentucky, not far from his Ohio home. On May 11, 2006, he made a prearranged, but quietly marketed, surprise appearance at
Towson University's annual Tigerfest celebration. He made another appearance on HBO's
Def Poetry, where he performed two poems, titled "Fuck
Ashton Kutcher" and "How I Got the Lead on
Jeopardy!". In April 2007, Chappelle set a stand-up endurance record at the
Laugh Factory Sunset Strip comedy club, beating comedian
Dane Cook's record of three hours and 50 minutes. In December of the same year, Chappelle broke his own record with a time of six hours and 12 minutes. Cook reclaimed the record in January 2008, with a time of seven hours. On November 19, 2009, Chappelle performed at the Laugh Factory again, where it was speculated that he would attempt to take back the record. However, according to the club owner, he was disqualified after he left the stage five hours into his routine. Chappelle again appeared on
Inside the Actors Studio and, in celebration of the show's 200th episode, he interviewed the show's usual host,
James Lipton. The episode aired on November 11, 2008. He appeared again on
Inside the Actors Studio in 2013, for its 250th episode. In February 2009, Chappelle did a four-hour set at
Comic Strip Live in New York. In August 2011, Chappelle appeared at Comedy Jam in San Francisco. (left) stand in front of a
C-17 Globemaster III at
Joint Base Charleston, S.C. (2017) In August 2013, Chappelle returned to full-time touring stand-up, as a headliner, when he was featured during the Oddball Comedy & Curiosity festival. Sponsored by
Funny or Die, Chappelle co-headlined with comedy act
Flight of the Conchords. During a stop in
Hartford, Chappelle walked off the stage due to heckling from the crowd that lasted throughout his entire performance. The heckling was so raucous that it drowned out Chappelle's voice over the P.A. system and included chants of "White Power", a line used in a ''Chappelle's Show'' episode, that was viewed as wildly uncalled-for and out-of-context by other audience members who later wrote about the event. A few days later, Chappelle stopped in Chicago for a performance. The comedy website ComedyHype.com acquired and released audio of him on stage responding to the heckling. Chappelle referenced the Hartford incident, stating that "young, white, alcoholic[s]" should be blamed for the prior incident, that he hoped North Korea would bomb Hartford, that in the future he would not stop in Hartford for gas, and finally summarizing his feelings on the situation by saying, "Fuck Hartford!" However, in August 2014 Chappelle returned to Hartford for a surprise appearance at the 2014 Oddball Festival and received standing ovations during his set. In June 2014, Chappelle made his first major New York City appearance in eleven years, performing ten nights at
Radio City Music Hall. Chappelle promoted the dates by appearing on
The Today Show,
The Tonight Show Starring Jimmy Fallon and
Late Show with David Letterman. In 2015, Chappelle appeared in the
Spike Lee film
Chi-Raq, his first film role in 13 years.
2016–2019: Career comeback On November 12, 2016, Chappelle made his hosting debut on
Saturday Night Live the weekend after
Donald Trump won the
2016 presidential election. The show also featured
A Tribe Called Quest as the musical guest. In his opening monologue, Chappelle tackled Trump and the election head on. He ended his monologue by stating, "I'm wishing Donald Trump luck, and I'm going to give him a chance, and we, the historically disenfranchised, demand that he give us one too." His performance on
SNL received widespread acclaim from critics and audiences alike. At the
69th Primetime Emmy Awards, he received an
Emmy Award for
Outstanding Guest Actor in a Comedy Series for his appearance. On November 21, 2016,
Netflix announced that they would be releasing three new stand-up comedy specials from Chappelle in 2017, with Chappelle being paid $20 million per special. The first two specials were released on Netflix on March 21, 2017, and hail directly from Chappelle's personal comedy vault. "Deep in the Heart of Texas" was filmed at
Austin City Limits Live in April 2015, and "The Age of Spin" was filmed at the
Hollywood Palladium in March 2016. The specials marked the comedian's first concert specials released in 12 years, and proved to be an immediate success as Netflix announced a month later that they were the most viewed comedy specials in Netflix's history. performing at
Royal Albert Hall in 2018 The third special,
Equanimity, was filmed in September 2017 at the Warner Theater in Washington, D.C., and then on November 20, 2017, Chappelle filmed a fourth special,
The Bird Revelation, at
The Comedy Store in Los Angeles. On December 22, 2017, Netflix announced the expansion of the deal to include
The Bird Revelation, which was released with
Equanimity on December 31. In September 2018, Chappelle's
Equanimity special received an
Emmy Award for Outstanding Variety Special (Pre-Recorded). In October 2018, Chappelle returned to the big screen as "Noodles", Jackson Maine's best friend and retired musician in
Bradley Cooper's directorial debut, a remake of
A Star Is Born. The film was a massive critical and commercial success. He was nominated along with the cast for the
Screen Actors Guild Award for
Best Cast in a Motion Picture. In 2018, Chappelle and
Jon Stewart joined forces for a duo comedy tour in the
United States, and across the
United Kingdom. He has also collaborated with
Aziz Ansari for three stand-up shows in
Austin, Texas, at the
Paramount Theater. In February 2019, Chappelle was nominated for and won the
Grammy Award for
Best Comedy Album for
Equanimity and
Bird Revelation. In 2019, Chappelle was chosen to receive the annual
Mark Twain Prize for American Humor presented by
John F. Kennedy Center for the Performing Arts. President of the Kennedy Center Deborah Rutter stated, "Dave is the embodiment of
Mark Twain's observation that 'against the assault of humor, nothing can stand'... and for three decades, Dave has challenged us to see hot-button issues from his entirely original yet relatable experience." The set of people honoring Chappelle included
Jon Stewart,
Bradley Cooper,
Morgan Freeman,
Lorne Michaels,
Tiffany Haddish,
Aziz Ansari,
Sarah Silverman,
Neal Brennan,
Q-Tip,
Mos Def,
John Legend,
Frederic Yonnet,
Erykah Badu,
Common,
SNL cast members
Kenan Thompson,
Michael Che and
Colin Jost, as well as
Eddie Murphy. The Prize was awarded at the Kennedy Center gala on October 27, 2019. The ceremony was broadcast on
PBS January 7, 2020. The
Mayor of the District of Columbia,
Muriel Bowser, declared the day of the award ceremony "Dave Chappelle Day" in Washington, D.C. On August 26, 2019, Chappelle's fifth Netflix special,
Dave Chappelle: Sticks & Stones, was released. The special garnered controversy, and backlash for jokes about abuse allegations against singers
Michael Jackson and
R. Kelly, as well as for jokes about the
LGBT community and
cancel culture. The following year,
Sticks & Stones won the
Grammy Award for Best Comedy Album. where audience members observed social distancing rules and wore masks to prevent the spread of
COVID-19. The title was chosen in reference to the
8 minutes and 46 seconds that police officer
Derek Chauvin knelt on the neck of
George Floyd, leading to his death. Chappelle touches on Floyd's murder and subsequent
protests and takes aim at
Don Lemon,
Laura Ingraham and
Candace Owens. Expanding on the concept of the socially distanced comedy presentation, beginning with a pair of performances in late June 2020 and officially kicking off with a Fourth of July celebration, "Chappelle and friends" hosted what became known as "Chappelle Summer Camp", which brought live performances to a masked, socially distanced audience at Wirrig Pavilion, in Yellow Springs, Ohio. These shows featured regular performances from comedians
Michelle Wolf,
Mohammed Amer and Donnell Rawlings, as well as Chappelle's tour DJ, DJ Trauma and frequent special guests including
Jon Stewart,
Chris Rock,
Louis C.K.,
Sarah Silverman,
David Letterman,
Bill Burr,
Michael Che,
Brian Regan,
Chris Tucker,
Kevin Hart,
Ali Wong,
Trevor Noah,
Tiffany Haddish, with musical guests
John Mayer,
Common, and many others. After several shows in July, some issues arose from neighbors' complaints of noise and disturbances, local zoning officials granted a special variance allowing the performances to continue through October 4, 2020. The Chappelle Summer Camp series of shows ended suddenly September 25, 2020, when Elaine Chappelle announced in a closed Facebook fan group that there had been a possible COVID-19 exposure in their inner circle, and all further performances were canceled. It was announced that Chappelle would return to host
Saturday Night Live the weekend of the
2020 United States presidential election, his second time giving a post-presidential election monologue. Due to the effect of the
COVID-19 pandemic on the vote count, the results were delayed and announced earlier that Saturday. In response to unfounded allegations that
Joe Biden's presidency had been stolen from
Donald Trump, Chappelle offered jokes ranging from Trump's handling of the pandemic to his resulting legacy, and the political future of the United States, in his 16-minute opening monologue, "Everyone knows how that feels. But here's the difference between me and you: You guys hate each other for that, and I don't hate anybody. I just hate that feeling. That's what I fight through. That's what I suggest you fight through. You've got a find a way to live your life. You've got to find a way to forgive each other. You've got to find a way to find joy in your existence in spite of that feeling". Critics and audiences praised the monologue describing it as "scathing", "illuminating" and "powerful". African American Film Festival Premiere of "Dave Chappelle In Real Life" in 2025 In December 2020, Chappelle's company,
Iron Table Holdings purchased a fire station near his
Yellow Springs, Ohio, home, with plans to convert it into a comedy club. He also retrofitted a mechanic's garage in the same village into a clubhouse, and dubbed it "The Shack", for podcasting. On October 5, 2021, Chappelle starred in his sixth Netflix special
The Closer. In
The Closer, Chappelle made jokes about gay and transgender people, particularly
transgender women, that some considered
transphobic - including one instance where he non-jokingly said "I'm team terf" and expressed support for JK Rowling. Simultaneously, Chappelle argued that he was not anti-transgender, bringing up his opposition to
North Carolina's anti-transgender bathroom laws and his friendship with the late
Daphne Dorman. The special was met with some backlash, including from students of Chappelle's alma mater
Duke Ellington School. CEO Ted Sarandos acknowledged that "storytelling has real impact in the real world" but refused to take down the special, stating that he "does not believe it falls into hate speech". In November 2021,
Saturday Night Live lampooned the controversy during its
Weekend Update segment, stating, "A Washington, D.C. art school is postponing renaming its theater, after alumni Dave Chappelle's Netflix controversy. Well, of course, because God forbid, you should name a building after someone problematic in Washington, D.C." In summer of 2022, Chappelle announced that he would not give his name to the
Duke Ellington School theater, instead insisting it should be named the Theater for Artistic Freedom and Expression.
Dave Chappelle: Live in Real Life, a documentary covering Chappelle's concerts in Yellow Springs during the COVID-19 pandemic, premiered at
Tribeca Film Festival in June 2021, followed by a series of roadshow events in the United States and
Canada and a
limited theatrical release on November 19, 2021. In the early hours of May 4, 2022, Chappelle was performing at the
Hollywood Bowl in
Los Angeles, California, as part of the
Netflix Is a Joke Festival, where he was tackled onstage by a member of the audience, who was swiftly subdued by security. The attacker was later found to have been armed with a replica handgun containing a knife blade. Chappelle's four-night stint at the Hollywood Bowl ties him with
Monty Python for the most headlined shows by a comedian at the venue. On November 12, 2022, Chappelle hosted
Saturday Night Live for the third time. On February 5, 2023, he received his fourth
Grammy Award for Best Comedy Album for
The Closer. On December 31, 2023,
Netflix released Chappelle's latest special,
The Dreamer, which debuted at No. 5 on the chart with 2.2 million views. On January 18, 2025, Chappelle hosted
Saturday Night Live in its first show of 2025, marking Chappelle's fourth time hosting. His 17-minute monologue included commentary on recent events, including the
January 2025 Southern California wildfires,
Jimmy Carter's death, and
Donald Trump's reelection to the United States presidency. == Controversies ==