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Ten Best Jake Gyllenhaal Movies

Updated on April 10, 2017
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Jake Gyllenhaal is one of the hottest young actors working today. The films that really launched his film career were October Sky and the dark indie darling, Donnie Darko. Since those early roles, Gyllenhaal has displayed a wide acting range in serious films dealing with gay relationships, mental illness, and serial murder. However, he is equally comfortable in action thrillers and romantic comedies. In what is probably his most notable performance, Gyllenhaal received an Oscar nomination for Best Supporting Actor for his role as a gay cowboy in the critically acclaimed Brokeback Mountain.

He is the son of director Stephen Gyllenhaal (Waterland) and screenwriter Naomi Foner (Running on Empty.) His sister is Maggie Gyllenhaal (Crazy Heart, The Dark Knight) who played his sister in Donnie Darko. His brother-in-law, Peter Sarsgaard, costarred with him in both Jarhead and Rendition to really keep things all in the family.

This ranking of Jake Gyllenhaal movies is based on the rankings of members at Rankography, a group of movie bloggers and other knowledgeable movie fans. After reviewing this list, I found myself thinking about how interesting most of Gyllenhall's movies have been. This is not only a testament to his acting chops but to his wise selection of film roles with only a few misses, such as Prince of Persia. It will be exciting to continue tracking Gyllenhaal's career.

Top 10 Jake Gyllenhall Films

1.
Zodiac
2.
Donnie Darko
3.
Brokeback Mountain
4.
October Sky
5.
Jarhead
6.
Source Code
7.
The Good Girl
8.
Brothers
9.
Love & Other Drugs
10.
Rendition

10. Rendition (2007)

Jake Gyllenhaal finally plays a serious grown up here. In Rendition, he stars as CIA analyst Douglas Freeman. This political wartime thriller aimed at showing the length at which a government will go under the guise of protecting freedom.

This film is a serious action drama which also features a star-studded cast that includes Meryl Streep, Alan Arkin, Reese Witherspoon, and Peter Sarsgaard. This was the first time that Gyllenhaal was casted with his current girlfriend, Reese Witherspoon, so it is also interesting to watch their chemistry develop.

Jake's ability to combine both dramatic and sympathetic tones lends credence to his role as a CIA agent who begins to suspect that the alleged terrorist he has been interrogating may have offered a false confession and is in fact innocent and wrongly accused. Because of his sensitivity in this performance, we can feel that his moral compass is being tortured as he struggles to decide whether to do what he knows is right or to remain on the side of his own country and government.

9. Love & Other Drugs (2010)

Love & Other Drugs opened to mixed reviews but the praise always seemed to focus on two points—it was lauded as a rare mature romance and was also acknowledged for the nuanced and charming performances of the two leads, Jake Gyllenhaal and Anne Hathaway.

This film is based on a non-fiction book that would seem to be rather boring and unlikely fodder for a big screen adaptation, particularly a romantic comedy. Jamie Reidy (Jake Gyllenhaal) is a young playboy who stumbles into the the fast-paced world of pharmaceutical sales after being fired from his last sales gig for sleeping with the boss's wife. At his new employer, drug behemoth Pfizer, he is tasked with pushing their anti-depressant, Zoloft, over their rival, Prozac. While meeting with Dr. Stan Knight (Hank Azaria), Jamie meets patient, Maggie Murdock (Anne Hathaway.) They quickly find themselves between the sheets in a no-strings-attached relationship—at least it starts out that way.

We soon learn that Maggie is in the early stages of Parkinson's and things start to get complicated. This film is both a romantic comedy and a serious drama dealing with this debilitating disease. With less appealing actors than Jake and Anne, the uneven mood and wobbly plot of this film may have gone completely off the rails. They manage to keep this one lively and entertaining.

Love & Other Drugs was directed by Ed Zwick (Crumb and Ghost World) and makes for an interesting date night flick that can be enjoyed equally by both sexes. It's also a good opportunity to see Gyllenhaal in a more mainstream and playful role than some of his darker and more complicated roles.

8. Brothers (2008)

Brothers is another favorite of mine and the last one that my husband will admit to shedding a tear for. This remake of a Danish tearjerker—both of which were inspired by Homer's epic poem, The Odyssey—also stars Tobey McGuire and Natalie Portman. In an interesting role reversal, Jake ditches his Jarhead uniform and plays Tommy Cahill, an ex-con burnout brother to decorated Marine hero, Capt Sam Cahill (McGuire.)

After McGuire's character goes MIA and is presumed dead in Afghanistan, Tommy comforts his wife, Grace Cahill (Portman), and begins helping around the house and providing solace to his sister-in-law and two nieces. Their relationship grows and becomes tragic when Sam returns home, alive but scarred from what he was forced to do while in captivity. McGuire, in a critically acclaimed performance, must come to grips with both his past actions and his current relationship with his family.

It was interesting seeing Jake play the immature misfit in this film (with requisite neck tattoo.) Despite having mostly played more straight-laced roles, he shows his range by diving into this more edgy character. And even though it was McGuire that earned most of the accolades for portraying a marine with PTSD, it was Gyllenhaal's calm and care-free bravado that helped balance the psychosis of his co-star.

7. The Good Girl (2002)

Many might remember The Good Girl as Jennifer Aniston's first foray into film after the end of Friends, but this charming film also starred Gyllenhaal as her tortured young love interest. Here he plays a slightly more contrived and banal Donnie Darko-type character. However, this movie is good satire and Jake nails this caricature of a post-adolescent misanthrope.

This was a daring, breakout role for Gyllenhaal, especially on the heels of Donnie Darko and October Sky. He shows his range as an actor who can be adept at understated comedy as well as more serious drama.

And while his role and performance is critical to the storyline, he is also careful not to overshadow Aniston's lead, as this film is definitely about her story and the character for which the title is named.

6. Source Code (2010)

Source Code was a notable action movie for a number of reasons. First, Gyllenhaal was given the chance to prove himself as a credible male lead in a sci-fi action film. Second, the film is also the sophomore directorial film feature of Duncan Jones (the son of legendary rocker David Bowie) whose first sci-fi thriller Moon (starring Sam Rockwell) won over critics and fanboys alike and is considered one of the best sci-fi films of the decade.

Source Code is set in Chicago in the near future and Colter Stevens (Gyllenhaal) is a government agent that is sent into the past to discover the perpetrator of a terrorist attack on a commuter train and thereby prevent the terrorists' future attacks. Throughout his journey, Stevens wrestles with questions of his own identity and mortality.

On the doomed train, he meets and falls in love with Christina Warren (Michelle Monaghan), one of the passengers destined to die in the attack. Stevens decides to tempt fate and change the course of the future to save Christina, much to the disapproval of his superior, Capt Colleen Goodwin (Vera Farmiga.)

This an exciting, action-packed film and Jake shows that he can successfully play the role of an action star (albeit a slightly less traditional one.) His confident performance also helps the audience suspend their disbelief at all of the potential plot holes that sometimes plague this time-travel flick.

5. Jarhead (2005)

Jarhead is a biographical war film based on former marine Anthony Swofford's 2003 book about his experiences in Saudi Arabia prior to Desert Storm and his time fighting in Kuwait. After Swofford's sobering stint in a ruthless boot camp, he is shipped off to the Middle East for active duty in Desert Shield. What unfolds is days of boredom in the hot desert sun, followed by the quick Desert Storm conflict.

Jarhead fell a bit flat for me and for most critics. I remember being quite excited to see this movie— mainly because I was excited to see what Sam Mendes (American Beauty, Revolutionary Road) would do with the material. Unfortunately, I think the boredom aspect of Swofford's experiences dominated the film so those expecting a typical war movie ended up disappointed. However, this is probably a realistic portrait of the war in the Middle East and definitely worth a viewing for the solid performances from Gyllenhaal, Jamie Foxx, and Pete Sarsgaard.

4. October Sky (1999)

October Sky is a true story about the struggle between generations in the mining town of Coalwood. Homer Hickam (Gyllenhaal) is a kid with a strong curiosity and a dream of going to college. He is inspired by the launch of the Sputnik rocket in the 1950s and starts playing around trying to build a toy rocket. His father, John Hickam (Chris Cooper), is a respected supervisor and safety minded leader of the men that go down in the local coal mines.

John dismisses Homer's obsession with rockets initially as child's play, knowing full well that Homer will one day end up in the mines with him and Homer's brother. However, Homer is inspired by his science teacher, Miss Riley (Laura Dern), to enter his rockets into a regional science fair that carries the potential of a college scholarship. Homer and his friends become obsessed with winning the fair but along the way he draws the ire of his father who ultimately forbids Homer from participating.

This film does an excellent job of highlighting the generational struggles between the old guard that fears change and also attempts to hold down someone trying to escape their lot in life, and the young, ambitious generation looking for a way out. Chris Cooper is one of my favorite character actors and he is excellent as Homer's crusty, but respected father. Gyllenhaal is fantastic as a wild-eyed teenager whose sky has no limit and achieves the impossible and leaves Coalwood to become a rocket scientist.

While many may think this is a family or children's movie, it is not. This is an excellent drama about a true story of achievement against all odds.

3. Brokeback Mountain (2005)

Ang Lee's Brokeback Mountain was one of the most decorated films of 2005 and quite a follow-up to his Hulk movie. By now, most people know the premise of this film; two male cowboys, Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal), are hired to herd sheep in Wyoming during a summer in their late teens. Over the course of some intense wilderness experiences, the two develop a deep bond that develops into something more after a night of heavy drinking.

During the rest of that summer, the two recognize that they have developed something far deeper than friendship but move on with their lives separately given that homosexuality is not even an option in their cowboy culture. Instead, they must deal with that love in the backdrop of marriages and 1950s conservative culture.

This unorthodox western film is clearly more of a drama than a cowboy movie. There are quite a bit of spoilers to be revealed when writing about this movie, so I will avoid doing so. I will say that the last scene is one of the most heart-wrenching, well-acted performances of the last decade. The film won was nominated for 8 Academy Awards, including nominations for both Gyllenhaal and Ledger, and won 3 for Best Director, Best Adapted Screenplay, and Best Original Score.

2. Donnie Darko (2001)

Donnie Darko is an American indie darling from the early 2000s. This film has a huge following among techies and GenXers, which is not surprising given the popularity of such TV serials like Lost and Heroes. The film covers the potential of an alternative universe and time travel.

Donnie Darko (Gyllenhaal) is a high school teen who narrowly escapes (or possibly doesn't) a fluke accident in which his room is destroyed by a fallen aircraft engine. The film covers the psychological challenges of his narrow escape. He begins having visions of a man-sized rabbit named Frank. Donnie Darko is a unique blend of drama, mystery, and science fiction.

While this film made very little at the box office (around $7 million), its large cult following has made it a long-term success. In fact, a 2-disc director's cut of the film was released in 2005 and a sequel in 2009, S. Darko. This film is also a unique opportunity to see Jake and his sister, Maggie Gyllenhaal, playing siblings in a movie.

1. Zodiac (2007)

Zodiac is one of my absolute favorite movies of the last 10 years. Directed by film genius, David Fincher (Se7en, The Social Network, and The Girl with the Dragon Tattoo), this movie chronicles the hunt for the notorious Zodiac serial killer who stalked the San Francisco Bay Area in the late 60s and early 70s. In typical Fincher fashion, the production design of this film is flawless, immersing the viewer back into the time period. Fincher manages to adapt the rather clinical non-fiction book into a taut thriller of a film.

Robert Graysmith (Gyllenhaal), a one-time cartoonist for the San Francisco Chronicle, becomes consumed with the hunt for the Zodiac killer. Graysmith actually went on to author the aforementioned book about this hunt. While Jake seems like an unlikely candidate to play the relatively awkward and nerdy Graysmith, he absolutely nails it and we empathize with his intense desire to solve this mystery. Gyllenhaal plays alongside a star-studded cast that includes Robert Downey Jr., Mark Rufallo, Chloe Sevigny, and Brian Cox.

Zodiac opened to fantastic reviews but made very little at the box office. So, for some of you, this might be a hidden gem of a film that is an absolute must see. It has since developed a bit of a cult following in the mystery thriller genre, primarily because of the outstanding performances by Gyllenhaal and Downey Jr.

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    • brimancandy profile image

      Brian 16 months ago from Northern Michigan

      I agree that Brokeback Mountain and Zodiac are great movies. I would also add Jarhead, Source Code, Brothers, and Proof To his best.

      There are only 3 that I didnt care for. End Of Watch, Enemy, and Accidental Love. His acting was great in End Of Watch, but the movie was beyond violent, and not my thing. Enemy, had good acting, but the story was bizarre, and didnt really make sense. Accidental love was horrible, most boring movie I have ever seen.

    • profile image

      Niktravelfit 3 years ago

      Great lens, really enjoyed it!

    • aaxiaa lm profile image

      aaxiaa lm 3 years ago

      I don't exactly like him as a personality or as an actor, but he picks his movies well, especially Brokeback mountain which makes me cry just thinking about it, also Heath... Great lens though!

    • WriterJanis2 profile image

      WriterJanis2 4 years ago

      Had to check this out again.

    • WriterJanis2 profile image

      WriterJanis2 4 years ago

      He really is so successful.

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      anonymous 4 years ago

      Jake Gyllenhaal has given us some great performances and there is only more to come...which you will review with your usual excellence!

    • raelcalu profile image

      raelcalu 5 years ago

      Donnie Darko should be on the top of the list...then Brokeback Mountain...then Zodiac...oh well.