Buddy Holly was an iconic American rock and roll singer and songwriter, known for pioneering the mid-1950s rock and roll era. He significantly influenced future music legends and his tragic death at a young age left a lasting impact on the music world.
This is based on winning 10 head-to-head matchups with other famous people, but also losing 20 head-to-head matchups.
Most recently Buddy Holly lost a matchup to Winston Churchill (#158) voted by someone from United States.