Ryan Phillippe

Ryan Phillippe rose to prominence as Billy Douglas on ABC’s One Life to Live, the first gay teenager on daytime television. He appeared on the show from 1992 to 1993 before starring in major films I Know What You Did Last Summer (1997), 54 (1998), Cruel Intentions (1999) and Gosford Park (2001).

Phillippe had supporting roles in Igby Goes Down (2002), Crash (2005), Stop-Loss (2008) and The Lincoln Lawyer (2011), and he led the USA series Shooter from 2016 to 2018. Phillippe wrote, directed and starred in 2014’s Catch Hell and reprised his role from the 2010 film MacGruber in Peacock’s 2021 series of the same name.

Phillippe was married to his Cruel Intentions costar Reese Witherspoon from 1999 to 2006, and the exes share daughter Ava and son Deacon. Phillippe moved on with Stop-Loss costar Abbie Cornish, but the pair called it quits in 2010. In July 2011, Phillippe welcomed daughter Kai with Alexis Knapp, whom he dated for four months in 2010.

The actor briefly dated Amanda Seyfried before getting engaged to model Paulina Slagter in December 2015, but the pair called off their engagement the following year. Phillippe dated Elsie Hewitt for two months in 2017, after which the model sued him, claiming he physically abused her. The exes settled outside of court in October 2019, just four days before his assault case was due to come before a judge.