Toby Keith Covel was an American country music singer, songwriter, record producer, actor, and businessman. Known for hits like 'Should've Been a Cowboy' and 'How Do You Like Me Now?!', Keith had a prolific career, releasing 19 studio albums and numerous chart-topping singles. He was also a film actor and founded the label Show Dog-Universal Music.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 75 head-to-head matchups.
Most recently Toby Keith lost a matchup to John Entwistle (#1469) voted by someone from Spain.