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Sony Pictures
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Jake Gyllenhaal is undeniably one of Hollywood's most sought-after actors. From his standout work in movies such as "Donnie Darko" to eventually becoming Mysterio in "Spider-Man: Far From Home," Gyllenhaal has been in many great movies over the years. He's been at this a long time, dating back to his time as a child actor in the early '90s. It all dates back to a smash hit, Oscar-winning Western with a star-studded cast.
The movie in question is "City Slickers," a Western/comedy directed by Ron Underwood, of "Tremors" and "The Adventures of Pluto Nash" fame. The movie centers on Mitch (Billy Crystal), who is terrified of his midlife crisis and convinces his pals Phil (Daniel Stern) and Ed (Bruno Kirby) to take part in a supervised cattle drive across the Southwest. Led by the gruff cowboy Curly (Jack Palance), they set out on a journey that proves to be more than they bargained for.
Gyllenhaal plays Mitch's son, Danny. Though not a big role, it was the role that set his career as an actor in motion. Speaking to NPR in 2015, Gyllenhaal reflected on how he got the role in a rather unconventional way. He had gone to a party with his parents, and Billy Crystal was there, who asked if Gyllenhaal would come in and read for his movie. As he recalled:
"I guess I must've been acting out ... and so I was making some fool out of myself. I think I remember what happened — he was leaving and I knew who he was and I picked up a chair from the table and I said, 'Here, take this. This is your party favor.' That's just me. It doesn't make much sense, but he loved it and he thought it was really funny."
City Slickers was a massive success in its day
Sony Pictures
Even though Jake Gyllenhaal had a relatively minor role in the movie, it's hard to pick a better first entry in one's filmography. Released in the summer of 1991, "City Slickers" proved to be an absolutely massive hit both critically and commercially. Against a mere $26 million budget, it made $179 million at the global box office.
Despite having very little screen time, Jack Palance also won the Oscar for Best Supporting Actor for his work as Curly. It was a resounding success on all fronts. So much so that it got a sequel in the form of 1994's "City Slickers II: The Legend of Curly's Gold." Gyllenhaal didn't reprise his role, which is just as well. The sequel was largely dismissed by critics and didn't perform nearly as well in theaters.
Even so, the first "City Slickers" is regarded as one of the best Westerns of the '90s and has endured as a classic of its era. Gyllenhaal went on to star in movies such as "October Sky" and "Donnie Darko" in the ensuing years. In 2005, he was nominated for Best Supporting Actor at the Oscars for his work in "Brokeback Mountain."
Some of his more recent credits include a leading role in Michael Bay's "Ambulance" and playing Dalton in the "Road House" remake, which is getting a sequel at Amazon. The actor will next be seen in this year's "The Bride!" which was directed by his sister, Maggie Gyllenhaal.
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