Jake Gyllenhaal smiling
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They say it’s important to remember where you came from, and Jake Gyllenhaal has certainly internalized that message. The actor has a lot of performances to be proud of in his career, but the first movie he was ever in holds a special place in his heart for a couple of reasons. Decades later, Gyllenhaal still counts a memento from the movie as one of his most prized possessions. 

Jake Gyllenhaal smiling

Jake Gyllenhaal | Robyn Beck/Getty Images

What is ‘City Slickers’ about? 

Gyllenhaal’s first movie was the 1991 western comedy City Slickers. The film stars Billy Crystal (Mitch Robbins), Daniel Stern (Phil Berquist), and Bruno Kirby (Ed Furillo) as middle-aged New York yuppies who go to a cattle ranch in New Mexico to deal with a middle crisis. It was a financial success, making $180 million on a $26 million budget, and a critical one. 

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