Rise to Fame
Born into a Hollywood family (his mother is a Golden Globe-winning screenwriter, his father a director), he had the connections but didn't coast on them. Donnie Darko flopped at the box office in 2001 and turned into a cult hit on DVD, the kind of career move you can't engineer. Brokeback Mountain in 2005 got him a BAFTA win and an Oscar nomination for Best Supporting Actor. He was 24, playing against Heath Ledger, and still walked away with the hardware.
In the Spotlight
After Prince of Persia underperformed in 2010, he quietly stopped chasing blockbusters and spent a decade working with Denis Villeneuve, David Fincher, and Dan Gilroy. For Nightcrawler he lost over 30 pounds and co-produced the film. The Oscar snub that year was widely treated as an embarrassment for the Academy. Now he's pivoted again: Road House (2024) became Amazon MGM's most-watched produced film debut ever worldwide, and Presumed Innocent earned him a Golden Globe nomination. Playing Iago opposite Denzel Washington's Othello on Broadway in 2025, he helped the run reportedly gross $2.8 million in a single week. The stage turn wasn't a creative detour. It was a statement.
Side Notes
The cinematographer who shot Nightcrawler is his godfather, which says something about how deep his Hollywood roots run even when he's playing outsiders. During filming, he improvised smashing a mirror, cut his hand badly, needed 46 stitches across a four-hour surgery, and was back on set six hours after discharge. He was born with a lazy eye. His sister Maggie Gyllenhaal directed him in The Bride! (2026), making the family business feel very literal.