Ryan Phillippe
Oct. 18 2011, Published 3:43 p.m. ET
Most known as Reese Witherspoon’s ex-husband, Ryan Phillippe started his acting career in I Know What You Did Last Summer and Cruel Intentions where he stared alongside Reese. Ryan continued acting in supporting roles in Gosford Park and Crash. It was not until later that Ryan took on another big leading role in Flags of Our Father’s. Since his divorce, Ryan has dated Abbie Cornish and Amanda Seyfried.