Jake Gyllenhaal’s 9 Best Movies, From ‘Brokeback’ to ‘Zodiac’

October Sky (1999)

Gyllenhaal was only 17 when he filmed Joe Johnston’s uplifting biopic about future NASA engineer Homer Hickam. The wholesome if occasionally downbeat story pits rocket-loving Homer against his traditional coal-mining father (Chris Cooper), who doesn’t believe his son’s dreams can come true.

Donnie Darko (2001)

Donnie seems to be sleepwalking through his life and he’s not quite sure what’s real and what isn’t, including Frank, the freaky guy in a grotesque bunny suit who tells him to do destructive things. Gyllenhaal is mesmerizing as the tormented teen in Richard Kelly’s now-classic cult movie.

“Donnie Darko” is currently streaming on Peacock, Pluto, Tubi and AMC+.

Brokeback Mountain (2005)

In Ang Lee’s sweeping adaptation of Annie Proulx’s short story, Gyllenhaal and Heath Ledger were both Oscar-nominated for their portrayals of two cowboys who fall in love in the 1960s, when being together publicly was not only not possible, but illegal. Gyllenhaal’s character Jack is the more emotionally vulnerable one in the relationship and damned if he doesn’t make us cry more than once in this movie that should have won Best Picture.

“Brokeback Mountain” is currently streaming on Peacock.

Zodiac (2007)

David Fincher’s dark drama about the real-life Zodiac killer remains an all-time nail-biter, especially the scene where Gyllenhaal’s character — Robert Graysmith, a cartoonist who’s become obsessed with the case — thinks he might be trapped in a basement with the killer himself. We feel the hairs on the back of our own necks rise as we urge him to get the hell out of there.

“Zodiac” is currently streaming on Apple TV+, Paramount+ and Pluto TV.

Prisoners (2013)

Gyllenhaal played a police detective who goes entirely too far in helping a father (Hugh Jackman) try to find his abducted daughter in “Dune” director Denis Villeneuve’s intense thriller.

Enemy (2013)

It’s twice the Gyllenhaal in Denis Villeneuve’s surreal arthouse movie in which the two characters meet and briefly swap lives … and symbolic spiders abound.

“Enemy” is currently streaming on Kanopy.

Nightcrawler (2014)

Hard to believe Gyllenhaal didn’t get an Oscar nom for this performance: His amoral Los Angeles newshound Lou Bloom is the worst kind of bottom feeder and his unwavering drive to succeed at any cost is truly terrifying. The actor got unnervingly thin to play this scary, intense character in what is, arguably, his definitive film.

“Nightcrawler” is currently streaming on Starz.

Spider-Man: Far From Home (2019)

The charming Mysterio (aka Quentin Beck) seems like a cool uncle to Peter (Tom Holland), one who can maybe fill the massive void left by Tony Stark. But, turns out his charm is as much of a smokescreen as his computer-generated illusions. Gyllenhaal plays that transition from nice guy to all-out villain perfectly.

“Spider-Man: Far From Home” is streaming on Disney+ and Fubo TV.

Velvet Buzzsaw (2019)

Gyllenhaal reteams with “Nightcrawler” director Dan Gilroy for this delightfully demented horror movie that co-stars René Russo and Toni Collette. He plays influential bisexual critic Morf Vandewalt, whose opinion can make or break an artist. He begins unraveling in spectacular fashion after a number of bizarre deaths tied to the art world. And we’ll never forget his delivery of the line, “The admiration I had for your work has completely evaporated.”

“Velvet Buzzsaw” is streaming on Netflix.