Montgomery Clift was an American actor known for his roles in classics like Red River and A Place in the Sun. He was a pioneering method actor who achieved critical acclaim and multiple Academy Award nominations.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 20 head-to-head matchups.
Most recently Montgomery Clift lost a matchup to Kenneth Branagh (#794) voted by someone from Canada.