Patrick Dempsey and Eric Dane in Grey's Anatomy (2005)

Patrick Dempsey, Eric Dane, James Pickens Jr., and Jesse Williams in Grey's Anatomy (2005)

Patrick Dempsey, Eric Dane, and Nora Zehetner in Grey's Anatomy (2005)

Patrick Dempsey, Eric Dane, Chyler Leigh, Kevin McKidd, and Jesse Williams in Grey's Anatomy (2005)

Patrick Dempsey and Ellen Pompeo in Grey's Anatomy (2005)

Patrick Dempsey, Sandra Oh, and Ellen Pompeo in Grey's Anatomy (2005)

Patrick Dempsey, Eric Dane, Chyler Leigh, Kevin McKidd, Sandra Oh, and Ellen Pompeo in Grey's Anatomy (2005)

Patrick Dempsey and Mark Saul in Grey's Anatomy (2005)

Patrick Dempsey and Kevin McKidd in Grey's Anatomy (2005)

Patrick Dempsey, James Pickens Jr., and Ellen Pompeo in Grey's Anatomy (2005)

Patrick Dempsey and Carla Gugino in Karen Sisco (2003)

Gina Gershon and Patrick Dempsey in Thanksgiving (2023)

Reese Witherspoon and Patrick Dempsey in Sweet Home Alabama (2002)

Patrick Dempsey and Alessandro Borghi in Devils (2020)

Patrick Dempsey, James Pickens Jr., and T.R. Knight in Grey's Anatomy (2005)

Patrick Dempsey and Poppy Montgomery in Blonde (2001)

Patrick Dempsey, Eric McCormack, and Dion Anderson in Will & Grace (1998)

Colin Firth, Renée Zellweger, and Patrick Dempsey in Bridget Jones's Baby (2016)

Mary Stuart Masterson, Andrew McCarthy, and Patrick Dempsey in Heaven Help Us (1985)

Brendan Fraser, Joe Pesci, Patrick Dempsey, Josh Hamilton, and Moira Kelly in With Honors (1994)

Kirstie Alley, Barbara Carrera, Carrie Fisher, Kate Jackson, and Patrick Dempsey in Loverboy (1989)

Patrick Dempsey, Katherine Heigl, Justin Chambers, Sandra Oh, James Pickens Jr., Ellen Pompeo, Isaiah Washington, Chandra Wilson, and T.R. Knight in Grey's Anatomy (2005)

Patrick Dempsey, Hilary Swank, Mario, Hunter Parrish, April Hernandez Castillo, Jason Finn, and Jaclyn Ngan in Freedom Writers (2007)

Patrick Dempsey, Katherine Heigl, Kate Walsh, Justin Chambers, Eric Dane, Sandra Oh, James Pickens Jr., Ellen Pompeo, Sara Ramirez, Isaiah Washington, Chandra Wilson, and T.R. Knight in Grey's Anatomy (2005)

Mia Sara, Michael Caine, Bryan Brown, and Patrick Dempsey in 20,000 Leagues Under the Sea (1997)