Although Chappelle was a writer on series like "Def Comedy Jam" in the early 1990s, this film was arguably his big break. In this Eddie Murphy classic, Dave Chappelle played Reggie Warrington, a confrontational comedian. His appearance added a hilarious layer to an already riotous film.

Chappelle's first starring role in a feature film came with "Half Baked," a stoner comedy cult classic. His role as Thurgood Jenkins, a lovable pothead, showcased his comedic talent and paved the way for his future success.

In this action-comedy film, Dave played a small but memorable role as Tulley, adding a dose of humor to the heist storyline led by Martin Lawrence.

Although not a film, this groundbreaking sketch comedy series is a crucial part of Dave's career. It blurred the lines between television and film and remains a touchstone for irreverent humor and incisive satire. See one of the classic clips above!

Directed by Michel Gondry, this documentary-concert film captures Dave's vision of a block party in Brooklyn, featuring legendary artists like Kanye West and The Roots. It's a testament to his ability to bring people together through laughter and music.

Dave's legendary HBO special, where he showcased his gift for storytelling and social commentary.

Airing on Showtime, a brilliant performance that tackled issues like race, politics, and pop culture.

In this Oscar-nominated film, Dave Chappelle portrayed Noodles, a close friend and confidant of Bradley Cooper's character. See a clip above.

This Netflix special, which received critical acclaim and controversy, proved that Dave's comedic prowess was as sharp as ever.

Another Netflix hit where he fearlessly delved into sensitive topics, reaffirming his status as a comedic legend. Check out the trailer with Morgan Freeman.

Happy 50th, Dave Chappelle!