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)

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

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

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

Patrick Dempsey and Carla Gugino in Karen Sisco (2003)

Gina Gershon and Patrick Dempsey in Thanksgiving (2023)

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)