Total Recall

Jake Gyllenhaal's 10 Best Movies

To celebrate the 10th anniversary of David Fincher's acclaimed mystery Zodiac, we decided to look back at the best-reviewed work of its star.

by and | February 28, 2017 | Comments

In 2007, director David Fincher teamed up with Robert Downey Jr., Mark Ruffalo, and Jake Gyllenhaal on Zodiac, a potent murder mystery about the manhunt for the real life serial killer who terrorized northern California during the 1960s and 1970s. Gyllenhaal earned well-deserved praise for his portrayal of Robert Graysmith, the San Francisco Chronicle political cartoonist who helped decipher the Zodiac’s cryptic letters, but despite the film’s overwhelmingly positive critical reception, it was completely overlooked by the Academy Awards. Now that the film is officially 10 years old to the day, we thought it was the perfect time to look back at star Gyllenhaal’s best-reviewed films… including Zodiac.

10. The Good Girl (2002) 82%

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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9. Prisoners (2013) 81%

After his 2011 film Incendies earned a heap of acclaim — including a Best Foreign Language Film Oscar nod — French Canadian director Denis Villeneuve made his Hollywood debut with a gripping psychological thriller about a desperate man (Hugh Jackman) driven to extreme measures when his young daughter is abducted with her best friend. While much of the film rested on Jackman’s shoulders, he was supported by a stellar cast that included Viola Davis, Paul Dano, Melissa Leo, and Jake Gyllenhaal as the skeptical detective whose investigation into the disappearance is beset by false leads and a father obsessed with vigilante justice. The end result was a twisty, twisted mystery that impressed more than a few critics, like USA Today’s Claudia Puig, who noted that “the plot raises complicated moral questions about how far an anguished person will go for the love of a child. At the same time, it sets up an intricate, horrifying mystery with breathtaking skill.”

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8. End of Watch (2012) 85%

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.”

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7. Donnie Darko (2001) 86%

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.

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6. Lovely & Amazing (2001) 86%

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.”

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5. Brokeback Mountain (2005) 87%

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.”

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4. Zodiac (2007) 89%

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.”

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3. October Sky (1999) 91%

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.”

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2. Source Code (2011) 92%

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.”

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1. Nightcrawler (2014) 95%

After cutting his teeth writing screenplays for films like The Fall and The Bourne Legacy, Dan Gilroy made his feature directorial debut with Nightcrawler, an uncomfortably tense thriller about a socially awkward man (Gyllenhaal) who finds his calling as an ambulance-chasing freelance videographer. Gilroy spent years reworking his script around the character of Lou Bloom and found a perfect partner in Gyllenhaal, who played an active part in the production of the film, lost nearly 30 pounds for the role, and turned in a powerhouse performance. With help from outstanding supporting players like Rene Russo, Bill Paxton, and Riz Ahmed, Nightcrawler went on to become one of the best-reviewd films of the year and earned Gilroy a Best Original Screenplay nod at the Academy Awards in the process. As Christopher Orr of The Atlantic pointed out, “Gyllenhaal is the same age that De Niro was in Taxi Driver and, like him, he is learning to channel an eerie, inner charisma, offering it up in glimpses and glimmers rather than all at once.”

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