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Jake Gyllenhaal's 5 Best Movies

September 22nd, 2012 8:00am EDT

Jake Gyllenhaal's 5 Best Movies You can say this about Jake Gyllenhaal: there’s little chance he’ll ever be typecast. Thanks to his deliberate choice to vary his roles as much as possible, Gyllenhaal continues to be one of the most unpredictable actors working today. He’s done big budget blockbusters (Prince of Persia: The Sands of Time) and smaller, contemplative indie films (Proof, Moonlight Mile). With each film, Gyllenhaal seems to pick roles in which he can challenge himself as an actor, rarely playing the same type of character more than once.

This weekend Gyllenhaal will continue to surprise audiences with a gritty, manic performance in End of Watch. Directed by David Ayer (Street Kings, Harsh Times), Gyllenhaal plays a Los Angeles police officer who crosses paths with a powerful drug cartel that won’t hesitate to take down a “do gooder” cop. The film co-stars Michael Pena as Gyllenhaal’s partner and marks Gyllenhaal’s first foray into the “found footage” brand of filmmaking.

To get ready for the release of End of Watch, here’s a look at Gyllenhaal’s five best movies from a career that has some serious hits (Brokeback Mountain) and serious misses (The Day After Tomorrow).

5. Source Code (2011, dir. Duncan Jones)

Director Duncan Jones’ feature film debut, Moon (2009), announced the arrival of a new filmmaking talent who had no problem creating mind-bending stories that may not leave audiences satisfied. His second feature, Source Code, starred Gyllenhaal as a soldier whose mind is inserted into the memory of a man who died during a terrorist attack on a Chicago commuter train. That’s right! Gyllenhaal’s character must re-live the last eight minutes of the man’s life over and over again until he can find out who was responsible for the bombing.

While the basic plot seems like typical sci-fi fare, Jones takes the story in an entirely different direction than one might expect and Gyllenhaal expertly adapts to every twist and turn that is thrown at his character. Throughout the film, Gyllenhaal is either trapped in a non-descript room talking to other characters through a two-way monitor or scouring a train for the bomb or bomber. Somehow, though, Gyllenhaal manages to make every scene feel more suspenseful and critical than the last.

4. Zodiac (2007, dir. David Fincher)

Director David Fincher has a knack for getting amazing performances out of his actors. Gyllenhaal’s work in Zodiac is no exception. He plays a real-life journalist named Robert Graysmith who becomes obsessed with the Zodiac killer who terrorized California in the 1970s. Gyllenhaal is surrounded by some of the most talented actors working today (Robert Downey, Jr., Mark Ruffalo), but never once seems out of his depth.

A common theme in Fincher’s work is anxiety and paranoia, both of which appear copiously in Zodiac. Gyllenhaal’s character becomes obsessed with the Zodiac and the puzzles and clues he uses to taunt San Francisco police detectives. Eventually, he falls deeper and deeper into his obsession and Gyllenhaal plays him brilliantly, like a performance straight out of a Hitchcock movie.

3. The Good Girl (2002, dir. Miguel Arteta)

While most people remember The Good Girl as the first (and only) genuinely emotional performance by Jennifer Aniston, the film truly works because of Gyllenhaal’s convincing work as a mopey stock boy who adopts the name Holden (as in Holden Caulfield) to reflect his alienation. With a wonderful script by Mike White, The Good Girl is a quiet and tender story about exploration and temptation that follows Justine (Aniston) and Holden as a flirtation turns into an affair with disastrous results.

Gyllenhaal is perfectly cast as Holden, thanks to his big, puppy dog eyes and naturally soft voice. He plays Holden as a dreamer who’s blinded by his desire for a life with Justine. While early on Holden seems to be mature and wise beyond his years, Gyllenhaal unleashes his true childish selfishness as the film progresses. The Good Girl was one of the first movies to gain Gyllenhaal mainstream attention thanks to Aniston’s fame. He would use this opportunity to launch an ever-evolving and impressive career.

2. Brokeback Mountain (2005, dir. Ang Lee)

In one of the most beautiful and heartbreaking love stories of all time, Gyllenhaal plays Jack Twist, a nomadic cowboy whose love for another man is forbidden by his time and place. Gyllenhaal received an Oscar nomination for his performance, as did his co-star Heath Ledger, who plays Ennis Del Mar, Jack’s friend and lover.

The story follows the two men as they try to maintain the secrecy of their relationship while appearing to lead “normal” lives. Where Ledger is quieter and reserved, barely speaking unless absolutely necessary, Gyllenhaal is talkative, boisterous and emotional. The two characters balance each other perfectly in the film even though their time together is limited.

With Brokeback Mountain, Gyllenhaal showed a much wider range of acting ability than he had previously. For the first time, it felt like he complete let himself go and allowed the character to make his own choices. Hopefully we will get to see Gyllenhaal give this powerful of a performance again sometime in the near future.

1. Donnie Darko (2001, dir. Richard Kelly)

One of the most famous cult movies of all time, Donnie Darko launched the career of Gyllenhaal as well as writer/director Richard Kelly. If you’ve seen Donnie Darko once, you’ve seen it three or four times since a single viewing will never give you the answers to all the questions you’ll have.

In the film, Gyllenhaal plays the title character, Donnie Darko, a melancholic and disturbed teen whose life becomes very strange after narrowly avoiding death. Donnie begins to have visions of a large bunny telling him to do terrible things. While Donnie isn’t sure if he’s dreaming or not, strange things start happening in his quiet suburban neighborhood and, though he doesn’t remember doing anything, Donnie has a feeling he has played a part in what is happening.

Donnie Darko continues to be a staple among midnight screenings around the country. Though still a young actor, Gyllenhaal’s work is what made the movie so successful. He completely throws himself into the bizarre world Richard Kelly created, never once appearing to question his director’s choices. The result is a wonderfully complex and unique film that showcased Gyllenhaal’s willingness to swim against the current and take on roles other actors would refuse.

Related: Brokeback Mountain, Donnie Darko, Jake Gyllenhaal, Source Code, The Good Girl, Zodiac, Starpulse Exclusives, Celebrity, Movies

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Photo Credits: Sole Productions, LLC; Twentieth Century Fox

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