[7] Chappelle has received two Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series for hosting Saturday Night Live in 2016 and 2020.

[8] Chappelle received six Grammy Awards for Best Comedy Album for The Age of Spin (2018), Equanimity & The Bird Revelation (2019), Sticks & Stones (2019) and The Closer (2021) and What's in a Name?

In addition to weekend stand-up gigs, he honed his craft at Monday night "open mic" performances at places such as the Boston Comedy Club on West 3rd Street, as late as the summer 1994.

[20][21] 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.

[12][25] He later appeared as a stand-up insult comic who targets patrons of a nightclub in the 1996 comedy The Nutty Professor starring Eddie Murphy, one of his major comedic influences.

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.

[12] In an interview with Oprah Winfrey that aired on February 3, 2006, Chappelle stated that burnout, losing his creative control, and a work environment that was uncomfortable, were some of the reasons he left the show.

[47][48][49] His decision to quit the show meant walking away from a $50 million contract with Comedy Central[38] and forming a rift with longtime collaborator Neal Brennan.

[3] Several musical artists, including Kanye West, The Roots, Erykah Badu, Mos Def, Dead Prez and Jill Scott, are featured in the movie both performing in the concert and in conversation off-stage; Chappelle brought Yellow Springs residents to Brooklyn at his own expense.

[55] In June 2005, Chappelle performed impromptu stand-up shows in Los Angeles,[15][56][57] then went on a tour that began in Newport, Kentucky, not far from his Ohio home.

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.

[84] 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.

[87] 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.

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 private event was held outdoors on June 6, 2020, in Yellow Springs, Ohio,[101] 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.

[102][103] 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.

[107][108] 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.

[126] 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.

[133] In his interview with Inside the Actors Studio host James Lipton, he said that his biggest influences in comedy are Richard Pryor, Eddie Murphy, Mort Sahl, Chris Rock, Paul Mooney, and Mel Blanc.

[140] Those to honor Chappelle at the event included Jon Stewart, Bradley Cooper, Aziz Ansari, Sarah Silverman, Chris Tucker, Frederic Yonnet and Lorne Michaels.

[142] His work, as well as that of Margaret Cho, was also the subject of a book by Canadian dramaturg Elizabeth Ludwig, American Stand-Up and Sketch Comedy, that was published at the end of 2010.

[149] In December 2021, Chappelle told the Yellow Springs, Ohio, village council that he would cancel his planned business investments, including his restaurant and comedy club, if it approved a zoning change to allow a multifamily affordable housing project.

Chapelle stated that he is not against affordable housing; he is against "the poorly vetted, cookie-cutter, sprawl-style development deal which has little regard for the community, culture and infrastructure of the village".

[154] In May 2024, in an appearance in Abu Dhabi, Chappelle said that "genocide is striking the Gaza Strip amid the Israel-Hamas war", while urging Americans to fight antisemitism so Jews do not feel like they need to be protected by Israel.

[156] Chapelle headlined a campaign event for actor Hill Harper, who was running against Congresswoman Elissa Slotkin in the Democratic primary ahead of the Michigan's 2024 U.S. Senate election, at Saint Andrews Hall in Detroit.

[167] His grand-uncle W. D. Chappelle Jr. was a physician and surgeon who opened the People's Infirmary around 1915, a small hospital and surgery practice in Columbia, South Carolina, when segregation prevented many African Americans from having access to healthcare.