One of the funniest shows we’ve ever seen premiered 21 years ago today (January 22). Click inside to check out some of the best sketches from the groundbreaking series!

Dave Chappelle is and will always be a household name in comedy. The Washington, D.C. native got his start studying 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 has often noted that being booed off stage while performing at Harlem Apollo Theater’s “Amateur Night” gave him the courage to continue his show business aspirations.

It’s a 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 which Chappelle also starred). 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.

Although the show coming to an end was sad for a lot of people, the laughter and iconic moments Chappelle’s Show gave viewers will never be forgotten or duplicated. To celebrate its legacy, check out a gallery of the best sketches from the legendary show.Slide in the comments and let us know which ones are your favorites and if you think we forgot any!