Rene Russo and Jake Gyllenhaal in Velvet Buzzsaw (2019)

Jake Gyllenhaal and Natalia Dyer in Velvet Buzzsaw (2019)

Jake Gyllenhaal and Nitya Vidyasagar in Velvet Buzzsaw (2019)

Stephen Colbert and Jake Gyllenhaal in The Late Show with Stephen Colbert (2015)

Jake Gyllenhaal and Zawe Ashton in Velvet Buzzsaw (2019)

Jake Gyllenhaal and Carey Mulligan in Wildlife (2018)

Jake Gyllenhaal and Riz Ahmed in The Sisters Brothers (2018)

Sarah Gadon and Jake Gyllenhaal in Enemy (2013)

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)