Total Recall

Total Recall: Jake Gyllenhaal's Best Movies

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

by | May 28, 2010 | Comments

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!


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.”


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.”


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.”


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.”


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.”


5. Donnie Darko

Time travel, a falling jet engine, and a dude in a bunny suit: From these disparate ingredients, writer-director Richard Kelly wove the tale of Donnie Darko, a suburban teenager (played by Jake Gyllenhaal) charged with repairing a rift in the fabric of our dimension. Or something. To call Darko “open to interpretation” would be understating the case a bit — it’s been alternately confounding and delighting audiences since it was released in 2001 — but its dense, ambiguous plot found stronger purchase with critics, who cared less about what it all meant than about simply having the chance to see an American movie that took some substantial risks. Though a few reviewers were confused and/or unimpressed (Staci Lynne Wilson of Fantastica Daily called it “derivative,” and Joe Leydon dismissed it as “a discombobulating muddle” in his writeup for the San Francisco Examiner), overall critical opinion proved a harbinger of the cult status the film would eventually enjoy on the home video market; as Thomas Delapa wrote for the Boulder Weekly, “If the sum total of Donnie Darko is hard to figure, there’s no questioning that its separate scenes add up to breathtaking filmmaking.” Despite a paltry $4.1 million gross during its original limited run, Darko returned to theaters in 2004 with a director’s cut — one whose 91 percent Tomatometer actually improved upon the original’s.


4. Lovely & Amazing

Years before he challenged taboos with Brokeback Mountain, Jake Gyllenhaal proved his versatility with script choices like the ones he made in 2001, which found him starring in Donnie Darko, Bubble Boy, and Nicole Holofcener’s Lovely & Amazing. Though Bubble Boy saw the widest release of the three (and some of the harshest reviews of Gyllenhaal’s career), Lovely & Amazing proved he could hold his own with a stellar cast that included Catherine Keener, Emily Mortimer, and Dermot Mulroney — and it proved that he was capable of rising to the challenge of a writer-director known for getting the best out of her actors. Here, Gyllenhaal stars as Jordan, a teenaged one-hour photo developer who earns the adulterous affection of his frustrated (and significantly older) co-worker, played by Catherine Keener. Holofcener’s films are known for focusing on women — and rightly so — but smart dramas need smart performances, and with his empathetic supporting turn here, Gyllenhaal more than held his own. Though it wasn’t a major commercial success, grossing only just over $4.2 million in limited release, Lovely & Amazing enjoyed a number of awards and nominations from critics’ associations, as well as acclaim from scribes such as Terry Lawson of the Detroit Free Press, who wrote, “For all its dirty talk and up-frontness, this is a family film — it’s about one family and the extended family of females. Any woman who sees it will recognize that, and any man who sees it will be better for it.”


3. Brokeback Mountain

Take a heart-wrenching short story by Annie Proulx, give it to award-winning director Ang Lee, and surround him with a rock-solid cast including Heath Ledger, Michelle Williams, Anne Hathaway, and — of course — Jake Gyllenhaal, and you’ve got Brokeback Mountain, one of the most talked-about (and award-winning) movies of 2005. Gyllenhaal and Ledger starred as Jack Twist and Ennis del Mar, a pair of Wyoming ranch hands whose tortured, almost completely unspoken affair has a profound impact on their lives — and the lives of their wives and children — over a period of several decades. Not your everyday Hollywood love story, to put it mildly — and to no one’s surprise, Gyllenhaal and Ledger earned more attention for their characters’ sexuality than for their performances in the roles, with a wide variety of pundits accusing the filmmakers of using Brokeback to further a political agenda; famously, one Utah theater owner canceled his engagement just hours before the first scheduled screening. Underneath all the hubbub, however, shone a beautifully acted love story with uncommon depth and intensity, and both Gyllenhaal and Ledger were richly rewarded for their work with an impressive number of awards and nominations, not to mention an impressive $178 million worldwide gross and reams of praise from critics, including Colin Covert of the Minneapolis Star Tribune, who wrote, “It has become shorthand to call Brokeback Mountain the ‘gay cowboy movie,’ but it is much more than that glib description implies. This is a human story, a haunting film in the tradition of the great Hollywood romantic melodramas.”


2. Zodiac

In the hands of an ordinary filmmaker, any attempt to tell the story of the Zodiac Killer might have been equal parts conjecture and garden-variety gore — after all, the serial murderer who terrorized the San Francisco Bay Area for years in the ’60s and ’70s, taunting the police with a series of cryptic letters, eventually disappeared, never to be identified. For director David Fincher, though, the truly interesting story didn’t lie so much with the Zodiac as it did with the men and women who devoted themselves to apprehending him — particularly Robert Graysmith, the San Francisco Chronicle cartoonist who broke the Zodiac’s code and eventually became an asset to the investigation. As the increasingly driven Graysmith, Gyllenhaal led the viewer on a darkening spiral of dead ends, wild goose chases, and grim obsession — and he anchored a showy cast that included Robert Downey, Jr., Mark Ruffalo, Chloe Sevigny, and Anthony Edwards. Unfortunately, the words “David Fincher” and “serial killer drama” sparked hopes that Fincher was returning to his Se7en roots, and the studio’s marketing campaign did nothing to set filmgoers straight; ultimately, despite a strongly positive reaction from critics, Zodiac was a non-starter at the box office, and by the time awards season arrived, this March release was all but forgotten. It deserved better, according to writers like the Toronto Star’s Geoff Pevere, who argued, “It makes you want to study it even more closely, in search of things you might have missed, trailing after leads that flash by in the relentless momentum of going nowhere fast. If you’re not careful, it might make you obsessed.”


1. October Sky

It isn’t often that NASA engineers get their own biopics — but then, most of them don’t have life stories as inspiring as Homer Hickam, the West Virginia native whose Sputnik-fueled fascination with rockets turned him into a teen science fair sensation (and, more importantly, helped him avoid working in the local coalmine). Based on Hickam’s autobiographical novel Rocket Boys, Joe Johnston’s 1999 drama October Sky gave audiences a rare slice of critically acclaimed drama during the cold winter months — and it provided a breakout role for Gyllenhaal, whose biggest credits to that point came through parts in a pair of his father Stephen’s movies and minor appearances in City Slickers and Josh and S.A.M. Though he was surrounded with talented co-stars, it fell to Gyllenhaal to carry the movie as the young Hickam and make audiences believe in not only his wide-eyed wonder at the stars, but his struggles with his distant, unsupportive father (played by Chris Cooper); his success was noted by critics such as Jeff Vice of the Deseret News, who correctly predicted that “Even if October Sky was a complete dud, the drama would still get points for being the movie that launched the career of a new star, Jake Gyllenhaal.”

In case you were wondering, here are Gyllenhaal’s top ten movies according RT users’ scores:

1. Zodiac — 92%
2. Donnie Darko — 91%
3. October Sky — 90%
4. Brokeback Mountain — 84%
5. Brothers — 80%
6. Jarhead — 77%
6. Lovely & Amazing — 77%
8. The Good Girl — 76%
9. Proof — 73%
10. Moonlight Mile — 72%

Take a look through Gyllenhaal’s complete filmography, as well as the rest of our Total Recall archives. And don’t forget to check out the reviews for Prince of Persia: The Sands of Time.

Finally, here’s a compilation of clips from City Slickers, featuring Gyllenhaal’s big screen debut as Billy Crystal’s son: