Richard Pryor was an American stand-up comedian and actor known for his sharp wit and storytelling ability. He won numerous accolades, including a Primetime Emmy Award and five Grammy Awards. He is widely regarded as one of the greatest stand-up comedians of all time.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 15 head-to-head matchups.
Most recently Richard Pryor lost a matchup to Neil Patrick Harris (#68) voted by someone from Canada.