Hailing from a performing family, Gyllenhaal’s acting career began in the 1990s, when he appeared in the 1991 film City Slickers at 11 years old. With a continued interest in acting throughout his ...

Remember Jake Gyllenhaal’s first role? He made his film debut at age 10 as Billy Crystal ’s adorable, rosy-cheeked son in the comedy classic City Slickers.