Can you imagine living next door to Jake Gyllenhaal? Every time you stepped outside to check the mail and ran into him, you’d never know which Jake you were going to get.
Such is the range of an actor who has played everything from a lovesick bubble boy to an unhinged existential superhero (all in the same year).
Love him or hate him, we can all agree Gyllenhaal has covered a lot of ground since his first movie role as Billy Crystal’s cringe-filled son in City Slickers. And despite being a handsome guy-next-door type with striking Siamese cat eyes, Gyllenhaal has effortlessly sidestepped the rom-com rut many up-and-comers fell into during the early aughts by taking left-field roles in small-budget indie flicks.
His need for slightly dark, character-driven stories even shines through in franchise blockbusters (Mysterio, anyone?). He is a master of naturalistic humor and dread in equal measure.
Now at the tender age of 40, Gyllenhaal continues his 20-plus-year stride with a role in Antoine Fuqua’s upcoming thriller about a 9-1-1 dispatcher who gets sucked into a phone call that’s more than meets the eye:
Sure, it seems a little pointless to worry about a possible kidnapping when the world is on fire, but Gyllenhaal sells it like such a pro we can’t help but buy what he’s selling. His chiseled jaw and anxiety-riddled eyes nail it again and again. Now with over 50 movies under his belt, it’s time we ranked the top ten. Buckle up.
Cover Photo: L. Cohen (Getty Images)
10. ‘Source Code’ – 2011
Is Jake Gyllenhaal good at solving puzzles? Source Code says yes. Give the man an Oscar for looking convincingly confused, asking for wifi with a straight face, then smirking with the smugness that only a denim shirt and tie can bring.
9. ‘October Sky’ – 1999
Sure, it’s one of the highest-rated movies on the list. But the reason this NASA biopic ranks in Gyllenhaal’s canon is that it was his breakthrough role. And for good reason too. Gyllenhaal carried his first Hollywood gig like a champ, laying out the earnest, charming, and evocative acting style that would become his hallmark. After this, his career took off like a… what’s the word?
8. ‘Zodiac’ – 2007
Audiences expected a true-crime movie about a still-at-large serial killer to be full of guts and gore. But David Fincher’s slow-burning psychological thriller focused more on the downward spiral of the people obsessed with catching the Zodiac Killer than on the mysterious man we still know nothing about. Jake is our lost innocence circa 2021.
7. ‘Lovely and Amazing’ – 2001
For a hot minute, Gyllenhaal was typecast as cougar bait. (Imagine that.) Before bagging Jen Aniston in The Good Girl, Jake wooed a much older Catherine Keener in this little comedy about four women grappling with their insecurities. In a story bursting with three-dimensional women, Jake offers counterpoint with a bubbly performance that shows off his goofier gifts.
6. ‘End of Watch’ – 2012
Another low-budge indie film, End of Watch takes the groove-worn LA police drama and reinvents it thanks to some of the best buddy cop moments ever committed to film (move over Turner and Hooch). The gritty naturalism of the movie’s directing and standout performances make this understated cop movie a flooring experience.
5. ‘Prisoners’ – 2013
There’s a reason director Denis Villeneuve and Jake Gyllenhaal have worked together so many times. Both are character-obsessed, have no qualms taking their time letting things unfold, and always build a rich inner life that bubbles beneath the surface. Prisoners is their best tag team, a film about how tethered we are to the ones we love and what lengths we’ll go to save them. Are we a prisoner to Jake Gyllenhaal’s dulcet stare? Maybe.
4. ‘Brokeback Mountain’ – 2005
Took long enough to make a hit movie about a couple of gay cowboys. Right?! When it finally happened the world was aflutter, thanks in large part to the powerful performances by Gyllenhaal and Heath Ledger. We knew that whatever happened to Jake’s career after this moment, we’d always have Brokeback Mountain.
3. ‘Nocturnal Animals’ – 2016
Some movies are dark and soul-rattling. And then there’s Nocturnal Animals, a film about personal nightmares wrought in such horrifying detail it will make you want to die alone. (Not sure that’s a recommendation.) Gyllenhaal pulls double duty here, both as a divorced author and the protagonist inside his new manuscript. Whatever ghosts were haunting him to evoke this tortured performance, we hope they never come over to our side of the fence.
2. ‘Donnie Darko’ – 2001
Gyllenhaal became a legend for ball-trippin’ nerds everywhere after delivering this pitch-perfect performance of a troubled teen embarking on an existential quest of mindbending proportions. This time-warping cult classic is full of eerie goodness, but it’s Gyllenhaal who cements the movie as a lasting incitement of unreality by bringing an entirely new energy to the screen.
1. ‘Nightcrawler’ – 2014
In the era of reboot, rehash, and recut, Nightcrawler is a wildly original story about a fledgling journalist’s cutthroat journey to the top of news television. All of Gyllenhaal’s acting powers merge, as we watch him slither through this shockingly fresh and devastating film. Not even a nod by the Academy? Robbed. At least it scores a number one in our book.
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