Ryan Phillippe and Chris Cooper in Breach (2007)

Ryan Phillippe, Laura Linney, and Craig Eldridge in Breach (2007)

Ryan Phillippe and Samaire Armstrong in The 2nd (2020)

Ryan Phillippe and Tim Robbins in Antitrust (2001)

Ryan Phillippe and Claire Forlani in Antitrust (2001)

Ryan Phillippe in Saturday Night Live (1975)

Ryan Phillippe, Balthazar Getty, Jason Marsden, Eric Michael Cole, Ethan Embry, David Lascher, and Scott Wolf in White Squall (1996)

Ryan Phillippe and Robert Altman in Gosford Park (2001)

Ryan Phillippe in Lady of the Manor (2021)

Ryan Phillippe and Bruce Davison in Breach (2007)

Ryan Phillippe, Rachael Leigh Cook, and Claire Forlani in Antitrust (2001)

Gillian Anderson, Sean Connery, Ryan Phillippe, Madeleine Stowe, Angelina Jolie, Gena Rowlands, and Jon Stewart in Playing by Heart (1998)

Ryan Phillippe, Jeff Bridges, Balthazar Getty, Jeremy Sisto, Eric Michael Cole, and Scott Wolf in White Squall (1996)

Ryan Phillippe, Reese Witherspoon, and Sarah Michelle Gellar in Cruel Intentions (1999)

Ryan Phillippe, Sarah Polley, and Piper Perabo in The I Inside (2004)

Ryan Phillippe, Laura Linney, and Chris Cooper in Breach (2007)