O. J. Simpson was an American football player and actor, celebrated for his legendary NFL career primarily with the Buffalo Bills. He became the first player to rush for over 2,000 yards in a season and won the Heisman Trophy in college. Post-retirement, he transitioned into acting and broadcasting.
This is based on winning 44 head-to-head matchups with other famous people, but also losing 42 head-to-head matchups.
Most recently O. J. Simpson lost a matchup to Rihanna (#105) voted by someone from United States.