Jimmy Wales is an Internet entrepreneur known for co-founding the non-profit free encyclopedia Wikipedia, and for-profit wiki hosting service Fandom. He has also been involved in other notable online projects.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 25 head-to-head matchups.
Most recently Jimmy Wales lost a matchup to Hilary Swank (#1162) voted by someone from Austria.