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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)

Jake Gyllenhaal (left) and Henry Cavill in "In the Grey." (42West)

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.…