Dave Chappelle

One of the defining comedians of the 21st century, Dave Chappelle experienced his breakthrough in the mid-2000s when his sketch show Chappelle's Show became a runaway hit on Comedy Central. The success of Chappelle's Show was the culmination of a decade's worth of hard work, ten years spent working the stand-up circuit and appearing on television and film whenever he could. By the late '90s, he was popular enough to star in the stoner comedy Half Baked, but Chappelle's Show captured Chappelle's satiric side, which tapped into the zeitgeist, a position that made him uneasy. He pulled the plug on his television show in the middle of its third season, then retreated from the spotlight. Over the next decade, he occasionally appeared at comedy clubs, finally returning to active duty in the late 2010s with regular touring and comedy specials. The son of a pair of professors, Dave Chappelle was born in Washington, D.C. on August 24, 1973. Growing up in Silver Spring, Maryland, Chappelle was drawn to comedy at an early age, cultivating an interest in drama while attending Duke Ellington School of the Arts. After his high school graduation, he headed to New York City, doggedly working at open mikes and comedy clubs over the next few years. He first gained attention in 1992 with an appearance on Russell Simmons' Def Comedy Jam, and was cast in Mel Brooks' Robin Hood: Men in Tights the following year. Over the next few years, Chappelle alternated between television -- he toplined a short-lived sitcom called Buddies in 1996 -- primarily in a guest spot on talk and comedy shows -- and movies, landing roles in Eddie Murphy's remake of The Nutty Professor and Michael Bay's Con Air. In 1998, he co-wrote and starred in Half Baked, a weed comedy also featuring Jim Bruer that turned into a cult classic; that same year, he appeared in the Nora Ephron romantic comedy You've Got Mail. In 2000, he had his first HBO stand-up special with Killin' Them Softly. All these projects built the foundation of the audience that flourished when he launched Chappelle's Show in 2003. Airing on Comedy Central, the show became a cultural sensation after its debut, thanks to such sketches as Chappelle's parody of Rick James, and turned the comedian into a valuable property. Viacom, the parent company of Comedy Central, offered him a $55 million contract to continue producing the show for two additional seasons but Chappelle walked away from it in the middle of the production of its third season in 2005. At that point, he had the footage for Michel Gondry's Dave Chappelle's Block Party -- a film documenting a free concert he threw in Brooklyn in 2004 -- in the can; it appeared in theaters in March 2006. Out of the glare of television's spotlight, Chappelle concentrated on low-key stand-up gigs, doing the occasional college tour as well as marathon sessions at the Laugh Factory on Sunset Strip. He began to reemerge on a larger stage in 2013, touring theaters across the United States. He returned to film with a role in Spike Lee's Chi-Raq in 2015, but it was his debut as a host on Saturday Night Live in November 2016 that catapulted him back into the spotlight. Soon, he signed a deal with Netflix, releasing four specials in 2017: The Age of Spin, Deep in the Heart of Texas, Equanimity, and The Bird Revelation, all spun off into audio albums that also won Grammys for Best Comedy Album. The next year, Chappelle appeared in Bradley Cooper's remake of A Star Is Born. Sticks & Stones followed on Netflix in 2019; like its predecessors, it won the Grammy for Best Comedy Album. During the COVID-19 pandemic's early days, Chappelle explored a few other avenues of performing -- some of this is captured in the 2021 doc Dave Chappelle: Live in Real Life, but he also released 8:46 on Third Man Records. He then returned to Netflix in 2021 with The Closer, and the streaming service was home for his next two specials: 2022's Grammy-winning What's in a Name? and 2023's The Dreamer. Chappelle branched out and made a cameo on "Parasail," a single from Travis Scott's 2023 album Utopia.
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