Paul Allen was an American businessman, investor, and philanthropist, best known for co-founding Microsoft with Bill Gates. He made substantial contributions to technology, sports, and scientific research, and owned the Seattle Seahawks and Portland Trail Blazers.
This is based on winning 18 head-to-head matchups with other famous people, but also losing 101 head-to-head matchups.
Most recently Paul Allen lost a matchup to Val Kilmer (#886) voted by someone from Spain.