Jo-Wilfried Tsonga is a retired French tennis player once ranked as high as world No. 5. Known for his charisma and powerful game, he won 18 ATP singles titles and reached the 2008 Australian Open final.
This is based on winning 8 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Jo-Wilfried Tsonga lost a matchup to Iggy Pop (#563) voted by someone from Austria.