Cheated on: Reese Witherspoon
Secret lover(s): Abbie Cornish

If any actor from the Cruel Intentions camp embodied their on-screen persona to a T, it's definitely Sebastian himself, Ryan Phillippe. Ironically, he married co-star and Hollywood sweetheart, Reese Witherspoon, and just like the fictional playboy, he gave himself to another women: Stop Loss hottie Abbie Cornish, who he shared the screen with as well. Reese did what any suspicious wife would do best and searched her husband's phone when he wasn't around. Unfortunately, she found a secret text conversation between the two and called her marriage quits. Art imitating life? You call it.