Stephen Colbert is an American comedian, writer, producer, political commentator, actor, and TV host. Best known for hosting The Colbert Report and The Late Show with Stephen Colbert, he has won numerous awards including nine Emmys.
This is based on winning 8 head-to-head matchups with other famous people, but also losing 10 head-to-head matchups.
Most recently Stephen Colbert lost a matchup to Diana, Princess of Wales (#50) voted by someone from United States.