Dave Chappelle began making appearances in films such as Robin Hood: Men In Tights and Half Bakedin the mid-1990s. He also began to make his way into television—getting his first in a series of TV deal that he would eventually be offered—at age 18.
Chappelle began making appearances in more films in the '90s with more significant parts. He starred in The Nutty Professor in 1996, alongside Eddie Murphy, and made his way into three popular films in 1998—Woo, You've Got Mail and Half Baked. The same year, Chappelle's father died, forcing the comedian to reevaluate his life. From there, he filmed the immensely popular comedy special Killin' Them Softly in 2000, followed by the film Undercover Brother in 2002.
In 2003, Dave Chappelle landed his own show on the Comedy Central cable network, entitled Chappelle's Show, winning two Emmy Award nominations for the wildly popular and controversial show, which frequently addressed race relations and featured musical guests.