Richard Harris was an Irish actor and singer, celebrated for his roles in films such as Camelot, Gladiator, and as Albus Dumbledore in the first two Harry Potter films. He won numerous accolades throughout his career.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 20 head-to-head matchups.
Most recently Richard Harris lost a matchup to Oprah Winfrey (#35) voted by someone from Austria.