Jake Gyllenhaal's 20 Best Movies of All Time, Ranked

Jake Gyllenhaal.

Though it's perfectly possible that right now L.A. native Jake Gyllenhaal is best known throughout the zeitgeist as the unconfirmed subject of Taylor Swift's recently revived magnum opus, it's also a statement of fact that the BAFTA-winning Oscar nominee has been one of the film industry's most reliable and consistently applauded leading men for at least two decades.

After making his film debut with a bit part in 1990's Oscar-winning City Slickers, the actor (whose parents are director Stephen Gyllenhaal and screenwriter Naomi Foner, his famous sister Maggie Gyllenhaal) appeared in some smaller movies before truly breaking through around the turn of the century. Premiering March 8 at SXSW, Gyllenhaal steps into sizable shoes as he reimagines Patrick Swayze's iconic turn as a bouncer with action prowess in Doug Liman's reboot of camp classic Road House. In preparation, we've rounded up and ranked the best Jake Gyllenhaal movies ever, the very best from an actor uncommonly talented and committed to every role.

Jake Gyllenhaal's Best Movies of All Time, Ranked

20. Ambulance (2022)

Michael Bay is basically a genre at this point: action, only more action. Though it opened to soft numbers worldwide, Ambulance garnered the director some of his most positive critical notices since The Rock. 

Gyllenhaal co-stars opposite Yahya Abdul-Mateen II, the pair playing adoptive brothers who hijack a "bus," as authorities say, in a desperate heist for the sake of a loved one's medical bills. It's important not to overhype Ambulance as something groundbreaking (it's actually a remake of a 2005 Danish thriller), but it avoids some of the excesses that Bay's critics regularly cite, it is indeed rather exciting at times, and the leads are world-class actors who deliver more than this kind of thing generally requires.

Related: 75 Best Action Movies of All Time

19. Spider-Man: Far From Home (2019)

As essential Spidey foe Mysterio, Gyllenhaal was the best part of the MCU's 23rd movie. A smaller-scale follow-up to the biggest superhero movie in history, Far From Home too often feels like mere connective tissue. The performances elevate it—most of all a deceptive (on-brand for Mysterio) mentor-student relationship between the villain and Peter Parker (Tom Holland).

Though its income would be later dwarfed by the historically successful Spider-Man: No Way Home in 2021, this hybrid of teen road movie and superhero actioner was Sony's highest-grossing title at the time, quickly becoming a member of the billion-dollar club.

18. Prisoners (2013)

Before Dune and before he'd established himself as one of Hollywood's most distinct talents, Denis Villeneuve directed an impressive ensemble including Gyllenhaal, Melissa Leo and Hugh Jackman (who carries the movie with some of his best work) in a heavy-handed box-office hit about a kidnapping and—even more—about the community surrounding it.

We're often a step ahead of the script, hardly ideal for a mystery; what's more aggravating is the self-seriousness of it all that's almost unintentionally funny at times. Still, the performances are top-notch and Villeneuve's aesthetics are never less than fully arresting.

Related: The 101 Best Thrillers of All Time, Ranked  

17. The Guilty (2021)

The peak pandemic era mostly just sucked—but it did provide audiences with some ingenious small-scale filmmaking. Netflix hit The Guilty was filmed over 11 days in lockdown; it's a remake of a 2018 French thriller about an emergency dispatcher who receives a distressing call. Riley Keough, Bill Burr, Ethan Hawke and Peter Sarsgaard round out the supporting cast in a successful exercise in minimalist suspense.

16. Lovely & Amazing (2001)

There's no denying Nicole Holofcener is a modern master of the intelligent, sharp and bittersweet female comedy, with Lovely & Amazing very much on-brand. It's about the lives, love lives, neuroses and insecurities of a New York matriarch and her three daughters. Gyllenhaal plays the teenage love interest of unhappily married, marginally talented artist Michelle Marks (Catherine Keener).

Lovely & Amazing is sharply observed throughout, an understated series of truth bombs (essentially the filmmaker's stamp) that's far removed from more conventional Hollywood dramadies.

15. Okja (2017)

Before breaking the longstanding foreign movie barrier for Best Picture, Bong Joon-Ho made this energetic fantasy about an oversized animal, and the contrasting motivations of the humans around her, for Netflix.

Gyllenhaal is an actor who famously isn't afraid to get really, really weird, perhaps a contrast with his chiseled movie-star looks. Okja is his most divisive performance. As a washed-up zoologist, the actor sounds a bit like Minnie Mouse and moves in a way most humans can't or won't. Audiences and critics remain divided on if it was too much or just enough.

14. Guy Ritchie's The Covenant (2023)

One of the more underrated movies of last year, and a high point in director Guy Ritchie's, let's face it, hit-or-miss oeuvre, The Covenant follows U.S. Master Sgt. John Kinley and interpreter Ahmed (Dar Salim), not based on a true story, but rather an assimilation inspired by real-life accounts.

The Covenant boasts some of Ritchie's crispest, most muscular direction, and the human drama really works thanks to an understated script.

13. Stronger (2017)

Watching Stronger now in context is somewhat shocking, given its director. It's hard to believe David Gordon Green, whose uninspired and laughable swings at the Halloween and Exorcist franchises still sting and haunt in all the wrong ways, helmed this quietly affecting biopic based on the memoir of Jeff Bauman, a Boston Marathon bombing survivor whose testimony was instrumental in authorities pinpointing and killing the terrorists responsible for the attack that left Bauman without legs above the knee.

Stronger is a movie about recovery, avoidant and hard-drinking Bauman's work going beyond the physical. Gyllenhaal excels, and Tatiana Maslany is just as valuable to the film as Jeff's girlfriend who would become his wife, Erin Hurley.

12. Enemy (2013)

Adapted from 2002 novel The Double, Enemy marks the first collaboration of Gyllenhaal and Villeneuve. The critically acclaimed French Canadian production follows two men who are physically indistinguishable, but otherwise quite different.

The low-key, deliberate Kafka-esque nightmare is non-resolved in one of the most frightening endings you'll ever see in a film—it comes out of nowhere and yet makes disturbing sense. Seriously, the final moments of Enemy will scare the hell out of you.

11. City Slickers (1991)

Gyllenhaal has a few minutes of screen time in City Slickers, so it's a stretch to call it a Jake Gyllenhaal movie, sure—but it's a reminder that the performer had presence from the beginning, and the movie is something of a low-key classic comedy in its right. It's also a reminder of a time when a family comedy could be genuinely heartwarming while being pretty irreverent, too.

Gyllenhaal plays the son of Billy Crystal's Mitch Robbins, a sales exec who embarks on a male bonding trip with his best buddies to the American West while in full midlife crisis mode. This is a finely acted comedy all-around, but of course it belongs to Jack Palance, who won the Academy Award for Best Supporting Actor as Curly.

10. Source Code (2011)

Duncan Jones' thrilling and romantic action sci-fi picture stars Gyllenhaal as a U.S. Army Captain determined to uncover the identity of a terrorist threat through a time loop minutes before a train bombing. Lean and convincingly performed, Source Code was a critical darling from the jump.

Related: The 100 Best Sci-Fi Movies of All Time, Ranked 

9. October Sky (1999)

The year 1999 is now rightfully regarded as one of the best in the history of film; one picture that often gets lost in the conversation is Joe Johnston's tender, earnest biopic based on Homer Hickam's autobiographical Rocket Boys.

This is Gyllenhaal's mainstream breakthrough, as the wide-eyed teen Hickam whose dreams of space are at odds with his coal miner father (Chris Cooper). An arresting supporting turn from Laura Dern as Homer's supportive teacher rounds out an altogether terrific family entertainment that pulls the heartstrings with finesse.

8. Wildlife (2018)

Paul Dano had already left a mark as one of the most versatile and unpredictable actors of his generation when he helmed his feature debut, about a young 1950s American family in turmoil.

Co-starring Ed Oxenbould and a sensational Carey Mulligan, Wildlife is a quietly impactful drama that was sadly drowned out in an awards season dominated by movies like A Star is Born, Bohemian Rhapsody and The Favourite. Though Gyllenhaal is terrific, this is Mulligan's show; as a housewife in existential crisis while her husband fights forest fires, she's what everyone talks about after they see Wildlife.

7.  End of Watch (2012)

In one of the best guy movies you're likely ever to see, a simple and well crafted thriller that should appeal to just about anyone, Gyllenhaal plays opposite Michael Pe?a in an action-heavy look at young cops operating in one of LA's most dangerous neighborhoods.

The movie has one critical flaw: villains that are cartoonish. Seriously, the street thugs are so exaggerated and wicked here that we're half expecting them to play a scene from a Transylvanian castle with with lightning and thunder overhead. But even that's not enough to draw much blood from one of the most moving, well-liked films about those who serve, and friendship between men, in modern memory.

6. The Good Girl (2002)

"We were obsessed with Mike White before it was cool," said a multitude of film critics, somewhere, presumably. In this black comedy The Good Girl, the White Lotus Emmy magnet wrote (and Miguel Arteta directed) hands-down the finest performance of Jennifer Aniston's career, the only one that truly grapples with the actress's enigmatic subtleties—not to mention her dark side.

Aniston stars as a bored Texas wife who reluctantly begins an affair with an angsty co-worker (Gyllenhaal). Though critics were very kind at the time, The Good Girl remains under-appreciated by audiences.

5. Donnie Darko (2001)

One could never form a list of the best, most influential American independent movies and not include Donnie Darko. In Richard E. Kelly's sci-fi teen thriller that served as Gyllenhaal's breakthrough, the actor plays a charismatic teen who sleepwalks, leading him to encounter a six-foot rabbit who bears an apocalyptic warning.

Coursing through the veins of frightening, absorbing Donnie Darko is a bizarre black humor that always works thanks in no small part to the film's lead. Best seen in the readily available director's cut, Donnie is lightning in a bottle, and you can't overstate its electricity.

4. Nocturnal Animals (2016)

There's undeniably a faction in the peanut gallery that wanted iconic fashion designer Tom Ford's movies to be glorified music videos, all style and no substance. What a disappointment for the skeptics it must have been when Ford became two for two, following the touching story of grief A Single Man with a mesmerizing gut punch that turns the revenge movie on its axis.

Co-starring a note-perfect, uncharacteristically chilly Amy Adams, Nocturnal Animals is a look at revenge via art. The two play toxic former lovers who exist and thrive in the worlds of book publishing and fashion respectively. Nocturnal Animals is spiritually ugly and visually orgasmic. A quiet, hateful stinger ending is, like pretty much everything on display here, perfect.

3. Zodiac (2007)

David Fincher‘s gorgeously photographed police procedural about the real-life Zodiac killer practically reset the bar for this kind of true crime thriller. Zodiac stars Gyllenhaal, Mark Ruffalo and Robert Downey Jr. (who appeared here mere months before Iron Man catapulted him back into superstardom). This is as scary a movie as any this century, arguably Fincher's finest hour.

2. Nightcrawler (2014)

If it isn't quite the very best movie he's appeared in, Nightcrawler remains Gyllenhaal's most stunning and unforgettable starring turn. The actor somehow altered his body composition in taking on the role of a lizard-like, soulless stinger who sees an opportunity to capitalize on audiences' demand for unethical, violent real-life content, in the streets of nighttime Los Angeles. Supporting turns from Rene Russo and an up-and-coming Riz Ahmed are similarly impressive.

Ultimately, Gyllenhaal wasn't nominated for a Best Actor Oscar. It's a shameful snub that audiences still talk about pretty regularly.

1. Brokeback Mountain (2005)

Speaking of the worst crimes in Oscars history, here's very likely the most tragic of them all, in nearly 100 years of broadcasts. In 2024 it's hard to find anyone who speaks favorably of Paul Haggis's clunky Crash, much less anyone who'd favor it above Ang Lee's stunning yarn of forbidden love in the American West. Despite the performance being in the shadow of Heath Ledger's colossal tour de force, Gyllenhaal won a BAFTA and was Oscar-nominated as Jack Twist.

Brokeback Mountain was a cultural leviathan back in its day, and its reputation has perhaps fluctuated, just a bit here and there, not least of all because it adheres to a longstanding tradition of ending gay movies in tragedy. Revisiting it nearly two decades later, it's clearly timeless.

Next, The 100 Best Movies of All Time, Ranked