Notable Partners: Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston, Taylor Swift, Katy Perry

Probably the most infamous ladykiller on this list, Mayer loves bicken back in white-tee Brando steez or draping himself head to toe in Visvim almost as much as he loves wooing whichever pop singer or actress is holding the "It Girl" title. And by wooing we mean scooping them up for like a year at best then discarding them and starting over. Game just rewinds.