Ryan Phillipe – Then
A lot of people out there have a soft spot for the bad boys, and early 2000s Ryan Phillipe fits that mold perfectly. Portraying bad boy roles in classics like Cruel Intentions and Crash, Phillipe was quickly deemed a heartthrob.
Along with that, though, he made waves in his private life when he tried the knot with costar Reese Witherspoon.
