Little known fact: Clooney was married to actress Talia Balsam from 1989 to 1993, before he scored his breakout role on "E.R." But for as long as audiences have known him, Clooney's been single, and staunchly so. After a five-year on-again, off-again romance with British model Lisa Snowdon, Clooney dated model/reality TV star/cocktail waitress Sarah Larson. During their relationship, in October 2007, he bet Michelle Pfeiffer $100,000 that he would never wed again -- one of Clooney's many quips about never wanting to settle down. In keeping with that promise, Clooney and Larson soon split. This year, he began dating Italian TV host Elisabetta Canalis.
Unlike Clooney, Mayer has had a tougher time maintaining a respectable reputation while crafting pop ditties and bedding a bevy of beauties. But that may be less because of his behavior and more because of what he says about it.
For instance: in 2002, Mayer dated actress Jennifer Love Hewitt, whose figure reportedly inspired his Grammy award winning hit, "Your Body Is a Wonderland." Four years later, he joked to the crowd at Hollywood's Laugh Factory that he never consummated his relationship with Hewitt because of a bout of food poisoning brought on by bad fish. Mayer later told Us Weekly that he apologized to Hewitt immediately after his impromptu, questionably raunchy appearance and that he "was really just making fun of myself."
Mayer's gaffe with his ex-girlfriend hasn't stopped some of Hollywood's hottest honies from flocking to his side. The singer has dated Jennifer Aniston, Jessica Simpson and Minka Kelly -- the same star Jeter also may or may not have wooed. And, as "Your Body Is a Wonderland's" commercial and critical success shows, he's managed to turn his penchant for the ladies into profit. If only Woods could say the same.