Ryan Phillippe, the best smile winner in high school, started as a teen model in Philadelphia before pushing the daytime TV envelope as a gay character on “One Life To Live” and establishing himself as a go-to pretty boy of the late ‘90s thanks to roles in “I Know What You Did Last Summer,” “54” and “Cruel Intentions,” which is the only time he shared the screen with ex-wife Reese Witherspoon. They met at her 21st birthday party in 1997, married and welcomed daughter Ava in 1999, had son Deacon in 2003 and separated in 2006. He moved into more critically acceptable fare like 2000’s “Way Of The Gun,” 2002’s “Gosford Park,” 2006’s Best Picture winner “Crash” and 2008’s “Stop-Loss.” He moved on in the romance department with Abbie Cornish (2007-10), Amanda Seyfried (2010-11) and Paulina Slagter (2012 to present). He became a dad again in July 2011 when actress Alexis Knapp, a former flame, gave birth to daughter Kailani.
Ryan Phillippe Search Results
Dates and Dust-UpsKim K. sparks romance rumors, jealous rages and more couples news.
Who Wanted Out?Did Pete or Ashlee pull the plug? Plus, what did in Jude and Sienna? Get the latest romance news ...
Bad Romance?Is Lady G's relationship on the rocks? Plus, Halle's ring and more romance news ...
Teens Gone WildThe "Skins" kids aren't Hollywood's only young rebels. See 20 more famous naughty teens.
100 Hot & SingleCheck out the 100 hottest, most eligible singletons Hollywood has to offer!
Happy for ReeseRyan Phillippe says he wishes nothing but happiness for Reese and her engagement.
'10 Romance RecapSee who hooked up and broke up in 2010.
Powerpuff BaleChristian Bale gives an impromptu concert of the "Powerpuff Girls" theme song, plus more celeb news in the Shortlist.
Best BodyKelly Osbourne and Jennifer Hudson tie for Fitness Magazine's body of the year title, plus more celeb news in the Shortlist.
Halloween Hookup?Did Amanda Seyfried get a treat from Ryan Phillippe?