Role Recall: 'Nightcrawler' Star Jake Gyllenhaal on 'Darko,' 'Brokeback,' and More

Nightcrawler’s Louis Bloom, the oily, robotic, not-quite-all-there Angeleno who will stop at nothing to succeed in the sleazy world of crime scene videography, is a far cry from Jake Gyllenhaal’s mostly warm-hearted characters. But if we’re looking for parallels between the actor his latest character, we can start with work ethic: Gyllenhaal hasn’t slowed down since he started acting in movies in 1991, and Nightcrawler marks the 33-year-old’s 25th movie release.

He began as a pre-teen in City Slickers (1991), came of age in dramas like October Sky (1999) and Donnie Darko (2001), and grew into a leading man in movies like Brokeback Mountain (2005), Jarhead (2005) and Zodiac (2007).

Along the way, Gyllenhaal became a major movie star in the process, landing lead roles in studio tent-poles like The Day After Tomorrow (2004) and The Prince of Persia. (2010) The latter didn’t pan out to be Pirates-esque franchise Disney hoped for, and it may be the best thing that could’ve happened to his career — and to movie lovers. In the years following Persia, Gyllenhaal has gravitated toward interesting, bold, and in largely experimental films like Source Code (2011), End of Watch (2012), Prisoners (2013), Enemy (2014) – and they’ve paid big dividends. His latest, Nightcrawler, might just be his best turn yet.

We took a drive down memory lane with Gyllenhaal in looking back at six of his most notable roles (which you can watch in the video above), including his breakout role in the cult favorite Donnie Darko and the “uncomfortable” but ultimately rewarding work he did alongside Heath Ledger in Brokeback Mountain.

City Slickers (1991)
Gyllenhaal grew up in a showbiz family: His father is director Stephen Gyllenhaal, and his mother is screenwriter Naomi Foner. Perhaps not surprisingly, his acting careerbegan early, and he made his movie debut at age 11 in this comedy hit, in which he played Billy Crystal’s son. Gyllenhaal says his early experience with Crystal helped shape him as an actor, and the comedy vet knew how to make him feel special: ”He signed a poster after [filming] that said, ‘Thanks for letting me be in your movie.’ I still have that poster.”

Donnie Darko (2001)
Ten years later, Gyllenhaal would star as the title character in Richard Kelly’s adored and enigmatic coming-of-age mind-bender, in which he shared the screen with his older sister, Maggie. Gyllenhaal says he’s all for engaging in debates about the meaning of Kelly’s cryptic cult hit, but for him, it’s relatively simple: “I just think it’s a movie about adolescence — the transition from adolescence to adulthood, and how inexplicably confusing it is.”

The Day After Tomorrow (2004)
Gyllenhaal graduated to the world of blockbuster moviemaking with Roland Emmerich’s disaster hit, which was shot during a dreary Montreal winter. “We had this huge water tank… and there were a lot of extras pissing in the water,” he says. “I never did.” The actor also does a stellar impression of his German director, when recalling a shot in which Gyllenhaal was told at the last minute to pretend as if five wolves were chasing him (they’d be added in later via CGI).

Brokeback Mountain (2005)
Gyllenhaal would receive an Academy Award nomination for his heartbreaking role as sheep-herder Jack Twist, playing opposite the late Heath Ledger in this critically acclaimed drama. “It was uncomfortable at times for us,” he says of sharing love scenes with Ledger. “But we also knew the bigger picture, and we knew what the story was about, and how much it meant to us, and how important it was… It became so much bigger than what we thought it would be. It was no longer ours at a certain point. It was everyone’s.”

Zodiac (2007)
In David Fincher’s crime drama, Gyllenhaal starred as a cartoonist-turned-detective tracking down San Francisco’s Zodiac killer. The notoriously demanding director (Se7en, Gone Girl) forced Gyllenhaal to redo take after take after take — even on a day in which the fact that the actor was running a high fever. Gyllenhaal doesn’t harbor any ill will toward the filmmaker, though: “David is extraordinary,” he tells us. “I learned so much from him. And I brought that with me to my career to this moment. He taught me so much. I’m very, very thankful.”

Nightcrawler (2014)
Gyllenhaal shed 20 pounds to play Louis Bloom, a socially awkward small-time criminal who finds a more fruitful career in the filthy world of freelance crime journalism. The actor, who also doubles as produceron the L.A. set, worked the late shift during filming: “My memory is really that 5-to-7 a.m. part of the night, where everyone becomes zombies after a 10-hour night of working… Some of the best work on that movie was done from 5 to 7, because that’s where that movie exists. [Nightcrawler] exists in that mindset.”

Nightcrawler opens everywhere Friday.