Andy Roddick is a retired American professional tennis player known for his powerful serve and aggressive playing style. He won the 2003 US Open and was a consistent top-10 player from 2002 to 2010.
This is based on winning 6 head-to-head matchups with other famous people, but also losing 15 head-to-head matchups.
Most recently Andy Roddick lost a matchup to Johnny Cash (#341) voted by someone from Canada.