Total Recall: Jake Gyllenhaal's Best Movies

We count down the best-reviewed work of the Prince of Persia star.

Jake Gyllenhaal

Jake Gyllenhaal has been a Hollywood leading man for only a little over a decade, but in that short period of time, he's taken on an impressive variety of roles -- from time-traveling teen to broken-hearted cowboy to war vet, with a bubble boy thrown in for good measure -- and racked up quite a bit of critical acclaim along the way. One thing he's never done, however, is take the lead in a swashbuckling mystical adventure epic -- at least not until this weekend, when he marks his debut as Prince Dastan in Prince of Persia: The Sands of Time. Watching Jake take out bad guys in sixth-century Persia got us to thinking about all the fine work he's done up 'til now, and you know what that means...it's time to look at Jake Gyllenhaal's best movies, Total Recall style!


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10. Brothers

If you're going to see a movie about a haunted Marine vet and his ex-con brother, and you know Tobey Maguire and Jake Gyllenhaal star in the lead roles, you might go in expecting to see Gyllenhaal as the soldier and Maguire as his no-good sibling -- but Jim Sheridan had other ideas for Brothers, his 2009 remake of Susanne Bier's Brødre. Here, it's Gyllenhaal, as Tommy Cahill, who finishes serving time for a robbery shortly before a crewcut-bedecked Sam Cahill (Maguire) goes off to war -- and it's Gyllenhaal who has eyes for the lissome wife his brother leaves behind (played by Natalie Portman). It isn't long before the family hears that Sam's helicopter has been shot down, killing everyone on board, but just when you think Brothers is going to turn into the story of a guilt-stained affair between a war widow and her brother-in-law, it takes a sharp turn into decidedly more dramatic territory, with a script (written by David Benioff) that wrings powerfully charged performances from all three of its young leads. American viewers have proven steadfastly unreceptive to movies about the current Middle East conflict, and this was no exception, but as far as most critics were concerned, the audience made a mistake; as Michael Phillips wrote for the Chicago Tribune, "It's easy to overlook a drama like Brothers, with its plain-spoken title and stern subject matter. Don't. The film is gripping---an honorable and beautifully acted addition to the tradition of homefront war stories."


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9. Jarhead

With a tagline like "welcome to the suck," you might expect Jarheads to be a Delta Farce-style comedy, but you'd be wrong -- while there's certainly humor to be found in this adaptation of Anthony Swofford's memoir of his time in the first Gulf War, it's of an altogether darker variety. Unlike most war films, which focus on either the horror or the glory of battle, Jarhead reveals the stultifying sameness experienced by many soldiers as they wait to ship out -- and the psychic toll exacted by a situation that turns young men into killing machines, then leaves them idle for weeks and months at a time. As Swofford, Jake Gyllenhaal is the movie's nominal star, but he gamely shares screen time with a solid ensemble cast that includes Jamie Foxx, Peter Sarsgaard, and Chris Cooper, leaving the focus where it belongs -- on the war, and its effect on one group of men as they grapple with boredom, fear, cheating spouses, and, finally, the hard work of readjusting to civilian life. It's decidedly light on epic battles, but as Peter Howell of the Toronto Star noted, "Jarhead makes its points less obviously than most war films, and with more brains than blood."


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8. Moonlight Mile

Inspired by writer-director Brad Silberling's real-life struggles with the death of a loved one (his girlfriend, actress Rebecca Schaeffer, was murdered by an obsessed fan in 1989), Moonlight Mile took a marquee cast, filmed them against a soundtrack stuffed with classic rock B-sides, and produced one of the handsomer dramas of 2002. Gyllenhaal stars here as the aimless, grief-stricken Joe Nast; set adrift after his fiancee is killed in a robbery, he goes to stay with her parents, even though, unbeknownst to them, he'd broken off the engagement shortly before her death. In spite of his mixed emotions about the whole situation -- and not a little guilt -- he ends up getting involved in their lives, entering into a planned business partnership with her father (Dustin Hoffman) and giving her mother (Susan Sarandon) a shoulder to cry on. Along the way, he also gets involved with a local bar owner (Ellen Pompeo), creating a situation in which something has to give. Unfortunately, that "something" turned out to be the patience of a surprising number of critics; despite its stellar pedigree and some fine work from its talented stars, quite a few writers felt Moonlight Mile never established enough depth to support its beautifully filmed melodrama. Still, for the slight majority, it was a Mile worth traveling -- including Glen Lovell of the San Jose Mercury News, who called it "One of the most generous and reassuring tragicomedies of this or any year."


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7. Proof

He's built a pretty eclectic filmography for himself, but no matter the project, Gyllenhaal has always had a knack for surrounding himself with talent, and 2005's Proof is a case in point: helmed by Shakespeare in Love director John Madden, this adaptation of David Auburn's Pulitzer-winning play united the formidable onscreen gifts of Anthony Hopkins, Gwyneth Paltrow, Hope Davis, and (of course) Gyllenhaal. The story of a supposedly insane mathematician (Hopkins) whose death throws the life of his daughter (Paltrow) into disarray (and possibly exposes cracks in her own sanity), Proof was one of many low-budget actors' clinics for Miramax, and it earned a Golden Globe nomination for Paltrow. As a student who combs through Hopkins' papers in search of undiscovered theorems, Gyllenhaal's main function may have been to provide a sounding board for Paltrow's character, but he used his screen time to help round out a quiet, layered drama that earned the praise of critics including the BBC's Stella Papamichael, who wrote, "For patient viewers, it does offer a carefully considered and ultimately inspiring examination of how the need for order and logic is less important than a willingness to embrace chaos."


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6. The Good Girl

Gyllenhaal ventured into romance -- of a sort -- with 2002's The Good Girl, a small-town drama from Chuck & Buck screenwriter Mike White that starred Jennifer Aniston as a morose department store clerk struggling to choose between her unsatisfying marriage and her affair with the unstable, Catcher in the Rye-obsessed co-worker played by Gyllenhaal. Infidelity, dead-end jobs, and small towns are nothing new for the movies -- indie films in particular -- but however familiar its premise, The Good Girl earned praise from critics thanks to the finely wrought honesty of White's script and strong performances from Aniston, Gyllenhaal, and their supporting cast (including John C. Reilly, Tim Blake Nelson, and Zooey Deschanel). Taking the cliche of a frustrated young man buried in Holden Caulfield and imbuing it with genuine depth, Gyllenhaal was a major part of why the Hollywood Reporter's Duane Byrge called it "An absorbing, slice-of-depression life that touches nerves and rings true."

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