Ryan Phillippe
Ryan Phillippe was one of the prettiest pin-up boys of the late 1990s. He and Reese Witherspoon, who co-starred together in Cruel Intentions (1999), tied the knot in a shotgun wedding in 1999 when Witherspoon was 23 and Phillippe was 25. They soon became parents to daughter Ava and son Deacon and were considered a golden (or at least golden-haired) couple until 2007. That's when Phillippe reportedly met Australian actress Abbie Cornish on the set of Stop Loss (2007). Witherspoon filed for divorce, and Phillippe stepped out with Cornish, who is about six years younger than his ex.
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