Patrick Dempsey and Isaiah Washington in Grey's Anatomy (2005)

Patrick Dempsey and Chyler Leigh in Grey's Anatomy (2005)

Patrick Dempsey, Katherine Heigl, Justin Chambers, Eric Dane, Brooke Smith, and Chandra Wilson in Grey's Anatomy (2005)

Patrick Dempsey, Kate Walsh, James Pickens Jr., and Isaiah Washington in Grey's Anatomy (2005)

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

Patrick Dempsey, Justin Chambers, and Brent Sexton in Grey's Anatomy (2005)

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

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

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

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

Patrick Dempsey, James Pickens Jr., and Chandra Wilson 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)