Tony Bennett was an American jazz and traditional pop singer renowned for his rich voice and timeless hits. He won 20 Grammy Awards and sold over 50 million records worldwide. Bennett co-founded the Frank Sinatra School of the Arts.
This is based on winning 11 head-to-head matchups with other famous people, but also losing 11 head-to-head matchups.
Most recently Tony Bennett lost a matchup to Ruth Bader Ginsburg (#1087) voted by someone from Canada.