Dan Quayle served as the 44th Vice President of the United States from 1989 to 1993 under President George H. W. Bush. Before that, he represented Indiana in both the U.S. House and Senate.
This is based on winning 8 head-to-head matchups with other famous people, but also losing 22 head-to-head matchups.
Most recently Dan Quayle lost a matchup to Sonia Sotomayor (#741) voted by someone from United States.