(Credits: Far Out / Entertainment One)
Fri 19 December 2025 16:15, UK
It feels like Jake Gyllenhaal has been around forever, which isn’t too far removed from the truth when the actor made his screen debut in 1991, with Ron Underwood’s City Slickers releasing in cinemas when the precocious actor was only ten years old.
As you’d expect from the child of two filmmakers who grew up in the business, he’s undergone several reinventions over the last three decades. Donnie Darko was the moment he truly announced himself as one of Hollywood’s brightest young talents, and he quickly became known as one of his generation’s most interesting performers.
His second reinvention came when he tried and failed to position himself as a blockbuster leading man. It may have been the highest-grossing video game adaptation ever made at the time, but Prince of Persia: The Sands of Time was still a flop, and Gyllenhaal was so disheartened by the experience that he took a decade-long sabbatical from big-budget cinema.
That’s when he arguably hit his peak, with standout performances in Duncan Jones’ Source Code, Denis Villeneuve’s Prisoners and Enemy, Dan Gilroy’s Nightcrawler, and Antoine Fuqua’s Southpaw, allowing him to stretch his artistic muscles, playing a wide range of characters in a genre-spanning array of eclectic films.
His third, current, and most baffling reinvention began when he returned to the studio arena with a villainous turn in Spider-Man: No Way Home, which lit the fuse on the star deciding that the best use of his time was to get shredded as fuck and headline a string of bombastic, and mostly crap, action flicks.
He can still pull out a great performance when he wants to, anchoring Fuqua’s remake of The Guilty to an engrossing effect, and making a string of shoddy pictures doesn’t make him a bad actor. Most people would agree that Gyllenhaal is good at his job, provided he’s got the right material to work with, but a high-profile director once called him the complete opposite.
In the period between October Sky and Donnie Darko, Gyllenhaal auditioned for what would have been his biggest and most daunting yet: Frodo Baggins in Peter Jackson’s The Lord of the Rings trilogy. When he was put through his paces in front of the New Zealander, though, he seriously fucked up.
“I did a scene with lines, and I didn’t have an accent,” he recalled. “Literally, he turned to me, he’s like, ‘You are the worst actor that I have ever seen.’” Needless to say, he wasn’t called back for a second audition, and it’s enough to make you wonder if even attempting an accent would have increased his chances, seeing as his fellow American, Elijah Wood, was ultimately cast.
Jackson doesn’t have a reputation for being a dick, so Gyllenhaal’s audition must have been truly woeful for the largely affable auteur to tell him, to his face, that he was the worst he’d ever come across during his years in the industry.
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