David Khari Webber Chappelle (/ʃəˈpɛl/ shə-PEL; born August 24, 1973) is an American stand-up comedian, actor and former sketch comedian. He debuted his half-hour TV special in 1998 and his hour-long TV special in 2000. He co-created and starred in the sketch comedy series Chappelle's Show (2003–2006) on Comedy Central before quitting in the middle of production of the third season. After a hiatus, Chappelle returned to performing stand-up comedy across the United States. By 2006, Chappelle was called the "comic genius of America" by Esquire magazine 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".

Chappelle has appeared in various films, including Robin Hood: Men in Tights (1993), The Nutty Professor (1996), Con Air (1997), You've Got Mail (1998), Blue Streak (1999), Undercover Brother (2002), Dave Chappelle's Block Party (2005), 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. Chappelle also starred in the ABC comedy series Buddies (1996). In 2016, he signed a $20-million-per-release comedy-special deal with Netflix and released six stand-up specials under the deal.

He released his first hour-long stand-up special Killin' Them Softly (2000) for HBO, followed by For What It's Worth for Showtime. He has released eight specials for Netflix. He has won six Grammy Awards for Best Comedy Album for The Age of Spin (2018), Equanimity & The Bird Revelation (2019), Sticks & Stones (2019), The Closer (2021), What's in a Name? (2022), and The Dreamer (2023).

He has received numerous accolades, including six Emmy Awards, six Grammy Awards, and the 2019 Mark Twain Prize for American Humor presented by the John F. Kennedy Center for the Performing Arts, considered America's highest comedy honor. Chappelle has twice won the Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series for hosting Saturday Night Live in 2016 and 2020.

David Khari Webber Chappelle was born on August 24, 1973, in Washington, D.C. His father, William David Chappelle III, was a professor of vocal performance and the dean of students at Antioch College in Yellow Springs, Ohio. His mother, Yvonne Seon (née Reed, formerly Chappelle), worked for Congolese prime minister Patrice Lumumba, is a Unitarian Universalist minister, and worked as a professor and university administrator at several institutions including Wright State University and Prince George's Community College. Chappelle has a stepmother and a stepbrother.

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 Theatre. He attended DC's Eastern High School for a short time before transferring to Duke Ellington School of the Arts, where he studied theater arts, graduating in 1991.

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. He quickly made a name for himself on the New York comedy circuit, even performing in the city's parks. 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. 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". 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 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 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.