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

Patrick Dempsey, Ellen Pompeo, Sara Ramirez, and Jesse Williams in Grey's Anatomy (2005)

Patrick Dempsey and Sara Ramirez in Grey's Anatomy (2005)

Patrick Dempsey, Meeghan Holaway, Andrew Leeds, Kevin McKidd, Sandra Oh, Ellen Pompeo, and Sara Ramirez in Grey's Anatomy (2005)

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

Patrick Dempsey, Meeghan Holaway, Andrew Leeds, Sandra Oh, Ellen Pompeo, and Sara Ramirez in Grey's Anatomy (2005)

Patrick Dempsey and Jesse Williams in Grey's Anatomy (2005)

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

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

Patrick Dempsey, Kim Raver, Eric Dane, and Chandra Wilson in Grey's Anatomy (2005)

Patrick Dempsey and Lorraine Toussaint in Grey's Anatomy (2005)

Patrick Dempsey, Ellen Pompeo, and Vanessa Marano 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)

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)

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

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)

Brendan Fraser, Joe Pesci, Patrick Dempsey, Josh Hamilton, Moira Kelly, and Todd Monteiro in The Super (1991)

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)