Alfred Matthew 'Weird Al' Yankovic is an American musician, comedian, and actor known for his humorous songs that parody contemporary hits and create style pastiches. His distinctive use of the accordion and music videos has earned him multiple Grammy Awards.
This is based on winning 7 head-to-head matchups with other famous people, but also losing 16 head-to-head matchups.
Most recently "Weird Al" Yankovic lost a matchup to James Gandolfini (#1051) voted by someone from Canada.