Jon Stewart is an acclaimed American comedian, writer, producer, and television host. He gained fame as the host of 'The Daily Show' on Comedy Central from 1999 to 2015, returning in 2024. His sharp political satire earned him numerous awards, including 22 Emmys.
This is based on winning 29 head-to-head matchups with other famous people, but also losing 50 head-to-head matchups.
Most recently Jon Stewart lost a matchup to Oprah Winfrey (#41) voted by someone from Canada.