Jake Gyllenhaal and Tim Post in Enemy (2013)

Jake Gyllenhaal and Maggie Gyllenhaal in Donnie Darko (2001)

Rebecca Ferguson and Jake Gyllenhaal in Life (2017)

Heath Ledger and Jake Gyllenhaal in Brokeback Mountain (2005)

Jake Gyllenhaal in Brokeback Mountain (2005)

Jake Gyllenhaal and David Harbour in Brokeback Mountain (2005)

Jake Gyllenhaal and Daniela Melchior in Road House (2024)

Bill Camp and Jake Gyllenhaal in Presumed Innocent (2024)

Jake Gyllenhaal in Presumed Innocent (2024)

Jake Gyllenhaal, Chase Infiniti, Ruth Negga, and Kingston Rumi Southwick in Presumed Innocent (2024)

Jake Gyllenhaal and Billy Magnussen in Road House (2024)

Jake Gyllenhaal and Lukas Gage in Road House (2024)

Jake Gyllenhaal in Perfecting Punches and Honoring Patrick Swayze in the 'Road House' Remake (2024)

Jake Gyllenhaal and Conor McGregor in Road House (2024)

Guy Ritchie, Jake Gyllenhaal, and Christopher Raphael

Michael Bay, Jake Gyllenhaal, Eiza González, and Yahya Abdul-Mateen II in Ambulance (2022)

Jake Gyllenhaal and Yahya Abdul-Mateen II in Ambulance (2022)

Michael Bay, Jake Gyllenhaal, and Danny Sharp in Ambulance (2022)

Jamie Foxx and Jake Gyllenhaal in Jarhead (2005)

Anthony Hopkins, Gwyneth Paltrow, and Jake Gyllenhaal in Proof (2005)

Robert Downey Jr., Jake Gyllenhaal, and Mark Ruffalo in Zodiac (2007)