Jake Gyllenhaal's Best Movies

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

by |

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 Peņa in moments so playful and true they make all other buddy cops look bogus by comparison."