One of the greatest comedians of all time turns 50 today (August 24)! To celebrate his life and legacy, check out a gallery of some of the best sketches from his groundbreaking show.

David Khari Webber Chappelle was born in Washington, D.C. and grew up in Silver Spring, Maryland. As a youth, Chappelle got his comedic motivation from Richard Pryor and Eddie Murphy. After his parents divorced, Dave stayed in Washington with his mother and spent summers in Ohio with his father. After transferring from DC’s Eastern High School, Chappelle studied theater arts at the Duke Ellington School of the Arts, where he graduated in 1991. Upon graduating, he moved to New York City to pursue his comedy career. Chappelle was booed off stage when he performed at Harlem Apollo Theater’s ‘Amateur Night.’ He states that this was the moment where he gained the courage to continue his show business aspirations.

Good thing that he kept going. In 1992, Chappelle started to gain critical and popular acclaim for his performance on Russell Simmons’ Def Comedy Jam on HBO. His popularity began to grow so much that he became a regular on late-night television shows (including David Letterman, Howard Stern and Conan O’Brien). Over the next couple of years, he continued working on his stand-up career while also appearing in films and sitcoms. He got his biggest break to date in 1996 when he appeared in The Nutty Professor. Two years later, he and Neal Brennan co-wrote the 1998 stoner comedy Half Baked. In 2000, Chappelle recorded his first hour-long HBO special Dave Chappelle: Killin’ Them Softly. He appeared in Undercover Brother in 2002 before turning his focus to the show that would launch him into unquestioned superstardom.

After reuniting with co-creator Neal Brennan, Chappelle debuted his weekly sketch comedy show on Comedy Central called Chappelle’s Show in 2003. The show parodied many aspects of American culture, including racial stereotypes, politics and pop culture. The show also featured musical performances from various hip-hop and soul artists. The show’s popularity skyrocketed to new heights so much that Comedy Central’s parent company Viacom offered Chappelle a $55 million (Dave would get a share of DVD sales) contract to continue production of Chappelle’s Show for two more years while allowing him to do side projects. Unfortunately, Chappelle started to become frustrated with the direction the show was going (and the entertainment industry’s tone deaf-ness to Black entertainers and viewers) and ended up walking away from it all.

Chappelle took a hiatus from comedy after departing from the show. He did sporadic shows over the next few years but returned to the stand up stage full-time in 2013. Since returning, he has won five Primetime Emmy Awards and four Grammy Awards for his stand-up specials (The Age of Spin, Equanimity & The Bird Revelation, Sticks & Stones and The Closer) and guest appearances (specifically Saturday Night Live). Although stand-up comedy is Chappelle’s first and biggest love and has got him the most accolades, everyone knows that there isn’t anything that could top the magic that was made on Chappelle’s Show. To celebrate the genius of the show and the man who it is named after, check out a gallery of the best sketches from the legendary show. Let us know which ones are your favorites and if we missed any. HAPPY 50TH BIRTHDAY TO DAVE CHAPPELLE THE GOAT!