Directed by Ron Underwood.  With Billy Crystal, Jack Palance, Daniel Stern, Bruno Kirby. On the verge of turning 40, an unhappy Manhattan yuppie is roped into joining his two friends on a cattle drive in the southwest.

Directed by Ron Underwood. With Billy Crystal, Jack Palance, Daniel Stern, Bruno Kirby. On the verge of turning 40, an unhappy Manhattan yuppie is roped into joining his two friends on a cattle drive in the southwest.

City Slickers from Jake Gyllenhaal: Movie Star  Jake made his big-screen debut playing Billy Crystal's outspoken son in the hit 1991 comedy.

City Slickers from Jake Gyllenhaal: Movie Star Jake made his big-screen debut playing Billy Crystal's outspoken son in the hit 1991 comedy.

Jacob Benjamin "Jake" Gyllenhaal (born December 19, 1980) is an American actor. Gyllenhaal began acting as a child with a screen debut in City Slickers. His breakthrough performance was as Homer Hickam in October Sky (1999) and he garnered an Independent Spirit Award nomination for playing the title character in the indie cult hit Donnie Darko (2001), in which he played a psychologically troubled teenager alongside his sister, Maggie Gyllenhaal. He subsequently appeared in another indie…

Jacob Benjamin "Jake" Gyllenhaal (born December 19, 1980) is an American actor. Gyllenhaal began acting as a child with a screen debut in City Slickers. His breakthrough performance was as Homer Hickam in October Sky (1999) and he garnered an Independent Spirit Award nomination for playing the title character in the indie cult hit Donnie Darko (2001), in which he played a psychologically troubled teenager alongside his sister, Maggie Gyllenhaal. He subsequently appeared in another indie…

25 Celebrities You Never Knew Were in Classic Movies (Jake Gyllenhaal In 'City Slickers')

25 Celebrities You Never Knew Were in Classic Movies (Jake Gyllenhaal In 'City Slickers')

Pin for Later: Wait, He Was in What?! Bet You Forgot These Actors Were in These Movies Jake Gyllenhaal, City Slickers Those baby blues were just as mesmerizing when he was a kid.

Pin for Later: Wait, He Was in What?! Bet You Forgot These Actors Were in These Movies Jake Gyllenhaal, City Slickers Those baby blues were just as mesmerizing when he was a kid.

Pin for Later: 15 Stars You Forgot Were Child Actors Jake Gyllenhaal Yes, cute little Gyllenhaal was acting — remember him as Billy Crystal's son in City Slickers?

Pin for Later: 15 Stars You Forgot Were Child Actors Jake Gyllenhaal Yes, cute little Gyllenhaal was acting — remember him as Billy Crystal's son in City Slickers?

Jake Gyllenhaal Remembers Making His Film Debut At 10 In City Slickers | PEN | Entertainment Weekly - YouTube

Jake Gyllenhaal Remembers Making His Film Debut At 10 In City Slickers | PEN | Entertainment Weekly - YouTube

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