Total Recall

Jake Gyllenhaal's Best Movies

In this week's Total Recall, we count down the best-reviewed work of the Prisoners star.

by | September 19, 2013 | Comments

Jake Gyllenhaal

In what promises to be the most nail-bitingly intense kidnapping drama since Ron Howard directed Mel Gibson in 1996’s Ransom, Jake Gyllenhaal and Hugh Jackman team up in this weekend’s Prisoners to find a pair of missing girls who may or may not have been lured into a van by gross Paul Dano. In honor of Gyllenhaal’s latest dramatic tour de force, we’ve decided to devote this week’s list to a fond look back at some of the brightest critical highlights from a wonderfully eclectic filmography that looks like it’s only begun to tap into his prodigious potential. It’s time for Total Recall!


10. 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.”


9. 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, unbeknown 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.”


8. 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.”


7. 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.


6. End of Watch

Most critics — and more than a few filmgoers — would agree that the found-footage gimmick has been more than played out since rising to prominence with The Blair Witch Project in the late 1990s. Still, it’s a powerful tool when used in the right way, as demonstrated by writer/director David Ayer’s End of Watch, which follows a cop/film student (Gyllenhaal) and his partner (Michael Pena) on patrol in the mean streets of South Central Los Angeles. While Ayer’s use of the found footage technique certainly proved divisive among critics, End of Watch earned a healthy $51 million at the box office, picked up a pair of Independent Spirit Award nominations, and enjoyed the respect of scribes such as Amy Biancolli of the San Francisco Chronicle, who wrote, “The best scenes are filmed inside the cruiser, dashboard shots that face inward instead of out, catching Gyllenhaal and Peña in moments so playful and true they make all other buddy cops look bogus by comparison.”


5. 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.”


4. 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 a $178 million worldwide gross and reams of critical 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.”


3. 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.”


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 1960s and 1970s, 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. Source Code

It’s a common complaint that there isn’t any room for original ideas in Hollywood anymore, but every so often, we’re treated to a movie like Source Code that proves an exception to the rule. Helmed by Moon director Duncan Jones from a script by Ben Ripley, this twisty sci-fi thriller follows the adventures of a U.S. Army captain (Gyllenhaal) whose latest mission — to prevent a catastrophic bombing on board a moving train — masks a horrible personal tragedy that his support team is keeping from him. Bolstered by a strong support cast that included Vera Farmiga, Michelle Monaghan, and Jeffrey Wright, and topped off by a thought-provoking ending, Source Code earned the applause of critics like the New Yorker’s David Denby, who wrote, “The movie is a formally disciplined piece of work, a triumph of movie syntax, made with a sense of rhythm and pace, and Gyllenhaal, who is always good at conveying anxiety, gives [his] desperation a comic edge.”

In case you were wondering, here are Gyllenhaal’s top 10 movies according RT users’ scores:

1. End of Watch — 86%
2. October Sky — 85%
3. Source Code — 80%
4. Donnie Darko — 78%
5. Brokeback Mountain — 77%
6. Zodiac — 74%
7. Jarhead — 66%
8. Moonlight Mile — 63%
9. Prince of Persia: The Sands of Time — 62%
10. Rendition — 62%

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 Prisoners.

Finally, here’s Gyllenhaal clowning around on the tennis court in the video for Vampire Weekend’s “Giving Up The Gun”:

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