Jake Gyllenhaal’s masculinity crisis |
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Finance Dying Parents Costing Millennials Dear Gen Z Investing In Le Creuset
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Jake Gyllenhaal’s masculinity crisis
With "In the Grey," Gyllenhaal performs machismo to the point of parody. What's muscling him out of better roles?
Published May 27, 2026 12:00PM (EDT)
When the COVID pandemic hit early in 2020, Jake Gyllenhaal was wrapping a year-long press tour promoting a unique new project. The actor — revered for his slate of complex, varied characters in films like “Brokeback Mountain” and “Donnie Darko,” and respected for his physical transformations for movies like “Nightcrawler” and “Southpaw” — wasn’t investing in a coffee brand or buying a sports team. Those things could be left to his contemporaries. What Gyllenhaal was promoting was intangible, something that money couldn’t buy and no agent could secure: his personal definition of masculinity.
“[In life], you try to be what your idea of a ‘tough guy’ is, but for me, it never really worked out well,” Gyllenhaal told W magazine in September 2019. At the time, he was making the rounds promoting his campaign for Calvin Klein’s Eternity fragrance, which had been reformulated to reflect modern tastes. Despite being marketed as an eau de parfum for men, the fragrance’s notes leaned more toward typically unisex scents. “All of our definitions about masculine and feminine are evolving … It doesn’t necessarily have to be only for a man. I really like that idea, particularly as the definitions of masculinity are in transition.”
Asked to explain his own interpretation, Gyllenhaal elaborated: “The more clichéd idea of what a man is is something I try to explore through the roles I play. I played a boxer, I played an officer, I played someone in the military, and there’s this sort of sense of a more classic idea of ‘male.’ [These roles] ask questions like, ‘What do we fight for?’ ‘What do we care about?’ I think those things are very important, and that they’re being lost. And they help lead me towards something else.”
Machismo is what pays the bills when the kind of mid-budget films that once boasted Gyllenhaal’s richest characters are being phased out by studio mergers and streaming platforms. He’s betting on red-blooded masculinity, and the odds are in his favor.
By the time April 2020 rolled around,........