John Mayer

John Mayer is about as famous for his relationships and soundbites as he is for his music. When it comes to his career, John has dominated both the pop scene as well as the blues and currently has seven Grammys. But his guitar skills are often overshadowed by his tumultuous love life. Having dated Jennifer Love Hewitt, Minka Kelly, Jennifer Aniston and Jessica Simpson, John became known as Hollywood's hottest playboy. John has also dabbled in comedy in his free time, preforming stand-up when he can and even filming his own VH-1 comedy special. In 2010, John got himself into a bit of hot water when he used a racial slur, called Jessica Simpson "sexual napalm" and discused his break up with Jennifer Aniston in an interview with Playboy after which John begins to try to distance himself from the media spotlight, eventually deleting his Twitter account and toning down his infamous pranks.