From the First Roles to the Most Recent of Hollywood’s Top Stars

Jake Gyllenhaal is easily one of the most talented actors of any generation. Gyllenhall first made his debut when he was ten years old in the film City Slickers in 1991. One of the more good-looking and physically fit men in Hollywood, Gyllenhaal has been nominated for countless awards.

After appearing in the fan favorite psychological thriller Donnie Darko, Gyllenhaal would go on to appear in films such as The Day After Tomorrow, Bubble Boy, Brokeback Mountain, and Nightcrawler. He last appeared as the villain Mysterio in the Marvel hit Spider-Man: Far From Home.