David Letterman is an American television host and comedian known for his work on late-night talk shows. He hosted 'Late Night with David Letterman' on NBC and 'Late Show with David Letterman' on CBS, influencing many others in the industry.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 26 head-to-head matchups.
Most recently David Letterman lost a matchup to Mark Webber (#1487) voted by someone from United States.