Birthday Boy Ryan Phillippe's Hottest Looks! (PHOTOS)
Making his first big splash in Hollywood, Ryan starred alongside fellow teen actors Sarah Michlle Gellar and Freddie Prinze Jr. in the 1997 horror I Know What You Did Last Summer. Since then, Ryan has shed his teen heartthrob status with roles in serious flicks such as 54, Gosford Park, Crash and The Lincoln Lawyer.
That's not all Ryan's done! Besides acting, Ryan has been linked to a bevy of Hollywood beauties after he split from his long-time wife Reese Witherspoon in 2007. After dating actress Abbie Cornish, Ryan romantically linked with Amanda Seyfried, Rihanna and even Demi Lovato!50 Cent and Bruce Willis which hits theaters September 20th.