- His maternal grandmother, Beatrice (Murray), was born in Grenada, and was a real estate broker and civil rights activist. His other grandparents were all African-American. Dave's paternal great-grandfather, William D. Chappelle (William David Chappelle), was an educationalist, a bishop of the African Methodist Episcopal Church, and President of Allen University. A paternal great-great-grandfather, Robert J. Palmer, was a land-owning merchant, who was a member of the South Carolina Legislature, then majority black, during Reconstruction.
- His SNL hosting debut generated the highest ratings in three years.
- Chappelle signed a deal to perform and produce and star in three specials for Netflix, each special worth $20 million.
- His mother, Yvonne K. (Reed) Chappelle, has been a professor at Howard University, Wilberforce University, Central State University and University of Maryland. She is also a Unitarian Universalist minister.
- Grew up in Silver Spring, Maryland; Yellow Springs, Ohio; and Washington, D.C., and still lives in Yellow Springs, Ohio, with his wife and children.
- Is one of the few (if not only) celebrities to do advertisements for both Coca-Cola and Pepsi.
- Met Muhammad Ali when he was three years old. A photo of their meeting is in the Bettman Archive.
- Was in talks to play Rick James in a film about James' life. Prior to James' death, due to some content objections by Rick James himself, it was decided the project would not happen. (2004)
- Was best friends and frequent co-writers with Neal Brennan. Their partnership ended when Chappelle abruptly left Chappelle's Show (2003) in its third season, though as of 2011 they have since patched things up with each other personally.
- #43 on Comedy Central's 100 Greatest Standups of All Time. He is the youngest person to make the list.
- Named his production company "Pilot Boy Productions" in reference to the many failed pilots in which he starred.
- He has two sons, Sulayman and Ibrahim, and a daughter, Sanaa Chappelle.
- Wife Elaine is a Filipina.
- Is currently in the beginning of talks about a movie involving his family and historical events they are fictionally involved in. (2004)
- He has gone on Late Night with Conan O'Brien (1993) 8 times so far, more appearances than he has had on all other talk shows combined.
- Sits in with Howard Stern when in New York. Chappelle is one of Stern's favorite comedians.
- Has continued to perform stand-up across the country, performing over 500 shows in the past three years.
- In his guest appearance on Comedians In Cars Getting Coffee it's shown that he has donated his Primetime Emmy, won for Outstanding Guest Actor in a Comedy Series for Saturday Night Live, to his former high school Duke Ellington School of the Arts in Washington DC.
- His father, William David Chapelle III, taught music and voice at Antioch College in Yellow Springs, Ohio.
- Due to the popularity of his show, Comedy Central's parent company Viacom cut a $50 million deal with him that will continue the production of Chappelle's Show (2003) for two more years and will allow him to do side projects.
- Living in Ohio after leaving for Africa on a spiritual retreat. (December 2005)
- Performed 10 sold-out shows at Radio City Music Hall in 2014.
- Made the Forbes Celebrity 100 List with $12 million in earnings.
- Is very good friends with fellow comedian Mario Cantone, who appears in the "Ask A Gay Dude" segment on Chappelle's Show (2003).
- Has won the Mark Twain Prize for American Humor in 2019.
- Has a brother, William, and a sister, Felicia.
- Was considered by Kevin Smith to play Fletch in his aborted "Fletch Won" reboot. But Miramax refused him.
- Turned down an offer to host the 2004 2004 MTV Video Music Awards (2004).
- Was considered by Darren Aronofsky for the role of Tyrone in Requiem for a Dream (2000), which ended up going to Marlon Wayans.
- Appeared on Actor Studio on 12th February 2006 (February 2006)
- Often appears opposite a Saturday Night Live (1975) star: Screwed (2000) (with Norm MacDonald), Half Baked (1998) (with Jim Breuer), and Undercover Brother (2002) (with Chris Kattan).
- His surname is pronounced "Shuh-pel".
- Currently has his own show titled Chappelle's Show (2003) on Comedy Central. (January 2003)
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