Dave Chappelle is an acclaimed American comedian and actor known for his satirical comedy series 'Chappelle's Show' (2003-2006). He has received numerous awards and is highly regarded for his stand-up specials.
This is based on winning 20 head-to-head matchups with other famous people, but also losing 45 head-to-head matchups.
Most recently Dave Chappelle lost a matchup to Nicolas Cage (#265) voted by someone from United States.