From his breakthrough in October Sky to his Oscar-nominated turn in Brokeback Mountain, these films are essential viewing for any Jake Gyllenhaal fan.

T he best Jake Gyllenhaal movies showcase how impressive the actor's career has been. He debuted in one of his father's (director Stephen Gyllenhaal) standout films, City Slickers and never looked ...

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 ...

Jake Gyllenhaal’s 9 Best Movies, ... Gyllenhaal and screenwriter Naomi Foner, he began acting at age 11 with a small role in the Billy Crystal comedy “City Slickers.” ...

Jake Gyllenhaal made his acting debut alongside Billy Crystal in the 1991 comedy "City Slickers," and has since earned accolades for his on-screen abilities. Gyllenhaal, 43, doesn't let his ...

Actress Maggie Gyllenhaal is the older sister of actor Jake Gyllenhaal. ... Crystal found Jake funny and casted him as his son in the 1991 film City Slickers.

Jake Gyllenhaal was photographed May 13 at ... More than 30 years into a career that started when he was 10 with a role in City Slickers, Gyllenhaal is — finally — learning how to navigate ...