Jake Gyllenhaal, Maggie Gyllenhaal, and Peter Sarsgaard at an event for Brokeback Mountain (2005)

Jamie Foxx, Sam Mendes, Lucy Fisher, Jake Gyllenhaal, Peter Sarsgaard, and Douglas Wick at an event for Jarhead (2005)

Sam Mendes, Lucy Fisher, Jake Gyllenhaal, Peter Sarsgaard, and Douglas Wick at an event for Jarhead (2005)

Jake Gyllenhaal at an event for Jarhead (2005)

Jamie Foxx and Jake Gyllenhaal at an event for Jarhead (2005)

Jake Gyllenhaal and Peter Sarsgaard at an event for Jarhead (2005)

Lucy Fisher, Jake Gyllenhaal, and Douglas Wick at an event for Jarhead (2005)

Jake Gyllenhaal and Anthony Swofford at an event for Jarhead (2005)

Laz Alonso and Jake Gyllenhaal at an event for Jarhead (2005)

Sam Mendes, Jake Gyllenhaal, and Peter Sarsgaard at an event for Jarhead (2005)

Chris Rock and Jake Gyllenhaal at an event for Jarhead (2005)

Ron Meyer and Jake Gyllenhaal at an event for Jarhead (2005)

Sam Mendes, Chris Cooper, and Jake Gyllenhaal at an event for Jarhead (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)

Jake Gyllenhaal in Spider-Man: Far from Home (2019)

Jake Gyllenhaal and Tom Holland in Spider-Man: Far from Home (2019)

Heath Ledger and Jake Gyllenhaal in Brokeback Mountain (2005)

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)