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Chappelle endorsed Andrew Yang in the 2020 United States presidential election.

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 The Kennedy Center. 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, Chrissy Teigen, 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, receiving 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, among other topics. In 2020, Sticks & Stones won the Grammy Award for Best Comedy Album.

In 2019, Chappelle was awarded the prestigious Mark Twain Prize for American Humor at the John F. Kennedy Center for Performing Arts. Those to honor Chappelle at the event included Jon Stewart, Bradley Cooper, Aziz Ansari, Sarah Silverman, Chris Tucker and Lorne Michaels. The award ceremony was turned into a television special and released on Netflix.

In January 2018 at the 60th Annual Grammy Awards, Chappelle received a Grammy Award for Best Comedy Album for his first two 2017 specials The Age of Spin & Deep in the Heart of Texas.

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. He has also collaborated with Aziz Ansari for three standup shows in Austin, Texas at the Paramount Theater.

Chappelle received his first Emmy Award in 2017 for his guest appearance on Saturday Night Live. In 2018, he received a Grammy Award for his Netflix-produced comedy album The Age of Spin and Deep in the Heart of Texas. Equanimity, another Netflix special, was nominated in 2018 for three Emmys and received the award for Outstanding Variety Special (Pre-Recorded). In 2019, Chappelle was selected to receive the Mark Twain Prize for American Humor, which is presented by the Kennedy Center as America's highest comedy honor. In 2020, Sticks & Stones earned Chappelle his third consecutive Grammy Award for Best Comedy Album.

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 2016, he signed a $20 million-per-release comedy-special deal with Netflix and, as of 2019, he has released five standup specials under the deal.

On November 12, 2016, Chappelle made his hosting debut on Saturday Night Live the weekend of Donald Trump winning 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. He donated the Emmy to his former high school while filming an episode of Jerry Seinfeld's Netflix series, Comedians in Cars Getting Coffee (Season 10, Episode 2: "Nobody Says, 'I Wish I Had A Camera'").

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.

In 2015, Chappelle appeared in the Spike Lee film Chi-Raq, his first film role in 13 years.

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 PA system and included chants of "White Power", a line used in a Chappelle's Show episode that was viewed as wildly inappropriate 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 multiple 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.

Chappelle has been known to make impromptu and unannounced appearances at comedy venues, and continues to do so following his post–Chappelle's Show return to standup.

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.

In August 2011, Chappelle appeared at Comedy Jam in San Francisco.

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. A monograph published by the University of Gothenburg titled Representations of Ethnicity in Stand-up comedy: A Study of the Comedy of Dave Chappelle examined the racial significance of language used in Chappelle's routines.

The show still plays in syndication on several television networks, despite the relatively small number of episodes, compared to most American syndicated television programs. Chappelle's abrupt departure from his show continues to be a focus of interviews and profiles of Chappelle and of Chappelle's own comedy. In Bird Revelation, Chappelle draws an analogy between his departure and the book Pimp, the memoir of Iceberg Slim. In 2009, his show was the subject of a book of critical essays, The Comedy of Dave Chappelle, edited by University of Maryland doctoral student K. A. Wisniewski.

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.

In February 2009, Chappelle did a four hour set at Comic Strip Live in New York.

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.

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.

In an interview with Oprah Winfrey that aired on February 3, 2006, Chappelle explained his reasons for quitting Chappelle's Show. He also expressed his contempt for the entertainment industry's tone-deafness regarding black entertainers and audiences:

During this time, Chappelle 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, such as a better working environment. He wanted to donate half of the DVD sales to charity. Chappelle expressed disdain at the possibility of his material from the unfinished third season being aired, saying 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. An uncensored DVD release of the episodes was made available on July 25.

Season 3 was scheduled to begin airing on May 31, 2005, but earlier in May, Chappelle stunned fans and the entertainment industry when he abruptly left during production and took a trip to South Africa. Chappelle said that he was unhappy with the direction the show had taken, and expressed in an interview with Time his need for reflection in the face of tremendous stress:

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. He made a surprise appearance on HBO's Def Poetry, where he performed two poems, titled "Fuck Ashton Kutcher" and "How I Got the Lead on Jeopardy!"

Chappelle was interviewed for Inside the Actors Studio on December 18, 2005, at Pace University's Michael Schimmel Center for the Arts. The show premiered on February 12, 2006. Four days earlier, he had introduced the musical tribute to Sly Stone at the 48th Annual Grammy Awards.

In June 2004, based on the popularity of the "Rick James" sketch, it was announced that Chappelle was in talks to portray James in a biopic from Paramount Pictures, also owned by Viacom. James' estate disagreed with the proposed comical tone of the film and put a halt to the talks.

In a June 2004 stand-up performance in Sacramento, California, Chappelle walked off the stage after berating his audience for constantly shouting "I'm Rick James, bitch!" which had become a catchphrase from his popular "Rick James" sketch. After a few minutes, Chappelle returned and resumed by saying, "The show is ruining my life." He stated that he disliked working "20 hours a day" and that the popularity of the show was making it difficult for him to continue his stand-up career, which was "the most important thing" to him. He told the audience:

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. 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. Another highlight of the event was the temporary reunion of 1990s hip-hop group The Fugees.

In 2004, he donated his time to Seeds of Peace International Camp, a camp located in Otisfield, Maine, which brings together young leaders from communities in conflict.

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.

Chappelle married Elaine Mendoza Erfe in 2001. They live with their two sons, Sulayman and Ibrahim, and their daughter, Sanaa, on a 65-acre (26 ha) farm near Yellow Springs, Ohio. He also owned several houses in Xenia, Ohio. Chappelle told Yellow Springs' residents in September 2006, "Turns out you don't need $50 million to live around these parts, just a nice smile and a kind way about you. You guys are the best neighbors ever. That's why I came back and that's why I'm staying."

In 2000, Chappelle recorded his first hour-long HBO special, Dave Chappelle: Killin' Them Softly, in Washington, D.C.. He followed this up with an appearance as "Conspiracy Brother" in the 2002 racial satire Undercover Brother.

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 so-called "stoner" film, a genre that includes the Cheech and 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.

Chappelle converted to Islam in 1998. He told Time in May 2005, "I don't normally talk about my religion publicly because I don't want people to associate me and my flaws with this beautiful thing. And I believe it is beautiful if you learn it the right way." Chappelle appears in a video explaining the religious backstory of the Well of Zamzam in Mecca.

He later appeared as a standup insult comic who targets patrons of a nightclub in the 1996 comedy The Nutty Professor starring Eddie Murphy, one of his major comedic influences. 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 Show' s 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.

Chappelle attracted the attention of TV 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.

Chappelle has appeared in several films, including Mel Brooks's Robin Hood: Men in Tights (1993), The Nutty Professor (1996), Con Air (1997), You've Got Mail (1998), Blue Streak (1999), Undercover Brother (2002), Chi-Raq (2015), and A Star Is Born (2018). His first lead role was in the 1998 comedy film Half Baked, which he co-wrote with Neal Brennan. Chappelle also starred in the ABC comedy series Buddies (1996).

Chappelle grew up in Silver Spring, Maryland, and attended Woodlin Elementary School. His parents were politically active, and family house visitors included Pete Seeger and Johnny Hartman. Hartman predicted Chappelle would be a comedian and, around this time, Chappelle's comic inspiration came from Eddie Murphy and Richard Pryor. After his parents separated, Chappelle stayed in Washington with his mother while spending summers with his father in Ohio. In high school he worked as an usher in Ford's Theater, the infamous location of Lincoln's assassination. In 1991, he graduated from Washington's Duke Ellington School of the Arts, where he studied theatre arts.

Chappelle was featured in a montage of random people telling a joke in the first episode of ABC's America's Funniest People, airing on September 13, 1990. Chappelle moved to New York City to pursue a career as a comedian. He performed at Harlem's famed Apollo Theater in front of the infamous "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. He quickly made a name for himself on the New York comedy circuit, even performing in the city's parks. 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, The Late Show With David Letterman, The Howard Stern Show, and Late Night With Conan O'Brien. Whoopi Goldberg nicknamed him "The Kid". At 19, he made his film debut as "Ahchoo" in Mel Brooks' Robin Hood: Men in Tights. He also appeared on Star Search three times but lost to competing comedian Lester Barrie; Chappelle later joked about the irony of his ultimately becoming more successful than Barrie. The same year, Chappelle was offered the role of Benjamin Buford "Bubba" Blue in Forrest Gump. Concerned the character was demeaning and the movie would bomb, he turned down the part. 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 OJ Simpson 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. Early in his career, Chappelle was called to perform after comedy veteran Chris Thomas, who was so good that Chappelle, though he had been warned, totally bombed.

David Khari Webber Chappelle (/ʃ ə ˈ p ɛ l / ; born August 24, 1973) is an American stand-up comedian, actor, writer, and producer. Chappelle is the recipient of numerous accolades, including two Emmy Awards and three Grammy Awards as well as a Mark Twain Prize. He is known for his satirical comedy sketch series Chappelle's Show (2003–2006). The series, co-written with Neal Brennan, ran until Chappelle's retirement from the show two years later. After leaving the show, Chappelle returned to performing stand-up comedy across the U.S. By 2006, Chappelle was called the "comic genius of America" by Esquire and, in 2013, "the best" by a Billboard writer. In 2017, Rolling Stone ranked him No. 9 in their "50 Best Stand Up Comics of All Time."