CAMERON DIAZ

In 2003, Cameron Diaz and Justin Timberlake took their romance public and were subsequently photographed everywhere. The media were quick to call her out for pouncing on Timberlake, who was 22 at the time, like a starving feline. Despite the headlines, the two meshed well and had everything going for them. Diaz had two Golden Globes and eight-figure acting gigs, while Timberlake had two Grammys (as a solo artist) and, of course, the infamous Super Bowl XXXVIII mishap. By 2007, however, their relationship had run its course and Justin and Cameron ended things amicably after four years.

Timberlake moved on to other conquests, while Diaz rebounded with the likes of Kelly Slater and Alex Rodriguez.