Dave Chappelle's stand up comedy career started when he was only 14 years old. Dave Chappelle's decision to become a comedian was taken after he read an article about Bill Cosby. So, Dave Chappelle moved to New York in pursuit of his career as a comedian...
In 1989, at the age of 16, the comedian Dave Chappelle performed his first stand up comedy show in front of the "Amateur Night" at the famed Apollo Theatre in Harlem. Even though he was booed off the stage, the comedian stated that that moment gave him the boost to continue his stand up comedy career. From there, Dave Chappelle took his show to New York comedy circuit and the comedian did stand up comedy even in city's parks.
In 1992 Dave Chappelle appeared on a Network Television in Def Comedy Jam with Martin Lawrence as the host and in 1995 appeared in one episode of Home Improvement. Dave Chappelle also appeared in "Buddies", a short lived sitcom.
In 1993, at only 20 years old, Dave Chappelle made his film debut in Robin Hood: Men in Tights, a Mel Brooks's film. In the same year, Dave Chappelle was cast a small part in Undercover Blues, as Ozzie. Also, in 1993, Dave Chappelle was offered the role of Bubba in Forrest Gump, but he turned down the offer, not-realizing what impact the film was going to have.
In 1994, Dave Chappelle played Ron in Getting in and in 1996 he played the role of the night club comedian Reggie Warrington in The Nutty Professor, starring Eddie Murphy, the comedian that along with Richard Pryor influenced the most of Dave Chappelle's show.
In 1997, Dave Chappelle also had a minor role in Con Air, and in 1998 played Kevin Jackson in You've got mail. in 1999 Dave Chappelle also played a minor role in Martin Lawrence's Blue Streak.