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 embarrassed by his father’s humdrum ad job that he introduced him as a submarine commander to his class.
But while City Slickers didn’t grant Gyllenhaal much screen time, the experience elicits a vivid recollection for the actor even 25 years later. “There’s a lot from my childhood that I don’t remember, and I remember everything from that,” he tells PEOPLE and Entertainment Weekly Editorial Director Jess Cagle in an excerpt from The Jess Cagle Interview. For the audition, he flew to Montana with his father for a read-through with the film’s director, Ron Underwood. Father and son booked a hotel for two days, and got the call Gyllenhaal landed the part before they left.
Watch more of The Jess Cagle Interview with Jake Gyllenhaal this week on PEOPLE.com
Of course, he’s since soared to Hollywood’s highest echelon, racking up a résumé fit for the A-list. Among his credentials are a breakout role in the critically acclaimed October Sky (1999), a starring part in the buzzy 2007 crime drama Zodiac, and a much celebrated performance in the Oscar-nominated Nightcrawler (2014). Still, City Slickers was a formative time for Gyllenhaal, marking his first steps into a career he’d later conquer.
Read more on Jake Gyllenhaal in the new issue of PEOPLE, on newsstands Friday
“It was an interesting, very complicated time. When you ask an actor who’s a kid why they get into it, I think it’s filled with a lot of very interesting and very complicated reasons,” Gyllenhaal, now 35, says. “Regardless of the whole exciting, shiny quality of the whole thing … I think there was something about being able to express it, and feeling comfortable expressing myself that was always there and I always loved.”
For more on Gyllenhaal’s role in City Slickers, and to catch his full interview with Cagle, check out the videos above.
Gyllenhaal will next be seen in Demolition, directed by Jean-Marc Vallée (Wild), out in theaters on Friday.