Remember Billy Crystal’s son in City Slickers that was so ashamed of his father’s ad sales job that he told his class he was a submarine commander? That was a 10-year-old Jake Gyllenhaal.

Long before Jake Gyllenhaal hit it big as a troubled teen in Donnie Darko or a cowboy romancing Heath Ledger in Brokeback Mountain, he played a bashful young boy in 1991’s City Slickers, so ...

Jake Gyllenhaal's first film 'City Slickers' was alongside actor Billy Crystal, who left a young Gyllenhaal with a poster from the movie and a sweet note.

More specifically, Jake was born to film director Stephen Gyllenhaal and screenwriter Naomi Foner, and got his early start in movies playing Billy Crystal's son in the 1991 hit City Slickers.

Gyllenhaal has a few minutes of screen time in City Slickers, so it's a stretch to call it a Jake Gyllenhaal movie, sure—but it's a reminder that the performer had presence from the beginning ...

The son of director Stephen Gyllenhaal and screenwriter Naomi Foner, he began acting at age 11 with a small role in the Billy Crystal comedy “City Slickers.” ...

City Slickers is a 1991 American comedy film directed by Ron Underwood and starring Billy Crystal, Daniel Stern, Bruno Kirby, Helen Slater and Jack Palance. Palance won an Academy Award for his ...

He made his acting debut at age 10 as Billy Crystal’s son in the classic comedy “City Slickers.” Ask 43-year-old Jake Gyllenhaal what he remembers about that first set and his small role and ...

Long before Jake Gyllenhaal hit it big as a troubled teen in Donnie Darko or a cowboy romancing Heath Ledger in Brokeback Mountain, he played a bashful young boy in 1991's City Slickers, so ...

More specifically, Jake was born to film director Stephen Gyllenhaal and screenwriter Naomi Foner, and got his early start in movies playing Billy Crystal's son in the 1991 hit City Slickers.

Gyllenhaal has a few minutes of screen time in City Slickers, so it's a stretch to call it a Jake Gyllenhaal movie, sure—but it's a reminder that the performer had presence from the beginning ...