1. Wes Hayden, "The Bachelorette" Season 5
During Wes Hayden’s limo-ride-confessional after bachelorette Jillian Harris sent him home, Hayden bragged that he was the first bachelor on the show to make it to the top four with a girlfriend, and then promptly promoted his band. As one of the most hated bachelors of his time, Hayden paved the way for future heartbreakers. Throughout his stint on the first season of “Bachelor Pad,” Hayden had time to redeem himself and struck up a romance with former “Bachelor” cast member Gia Allemand, but was still there for the wrong reasons. Oh Hayden— once a bad guy, always a bad guy!