Dave Chappelle was 18 in Robin Hood: Men In Tights - The Legend Had It Coming when he played the character 'Himself'.
That was over 31 years ago in 1993.
This was his first recorded movie acting credit (although may not technically be his first actual acting role).
Today he is 50, and has starred in 70 movies in total, 70 of those since Robin Hood: Men In Tights - The Legend Had It Coming was released.
In Robin Hood: Men In Tights - The Legend Had It Coming, I think Dave Chappelle looks: