10 best Jake Gyllenhaal movies

Jake Gyllenhaal in Southpaw
Jake Gyllenhaal in Southpaw, undoubtedly one of his best movie performances

Jake Gyllenhaal is a magnetic onscreen force; everything else melts into the background during his close-ups. His ‘look’ has a beautiful sadness that lends its self to disaffected, slightly unhinged characters.

He tends to pick subversive films where the disaffected and the unhinged are the heroes because the supposedly upstanding members of society running the system are the ones who are really sick like Patrick Swayze’s paedophilic self-help guru in Donnie Darko.

Gyllenhaal’s decisions as an actor are always interesting and never what we would expect so you have to pay attention during his movies.

Here are 10 of his best movies.

10The Good Girl – Tom ‘Holden’ Worther

The Good Girl
The Good Girl with Jake Gyllenhaal and Jennifer Anniston

Gyllenhaal plays Holden, a depressed, alcoholic teenage loner who falls for equally dissatisfied beauty counter clerk Jennifer Anniston.

Anniston is married to a stoner who shoots blanks.

She latches onto Holden, hoping to inject some excitement into her dull suburban life, and then freaks out when he becomes emotionally attached to her.
The Good Girl (Arteta, 2002, US) is a fairly unsatisfying film but Gyllenhaal is terrific as a kid who names himself after the disaffected hero of his favourite book. He seems aware that his life is doomed to misery before it has begun. Femme fatale Anniston is quick to take advantage of his temperament.

9 End of Watch – Brian Taylor

End of Watch
End of Watch sees Jake Gyllenhaal’s character and his partner become targets for the cartels

End of Watch (Ayer, 2012, US) is an incredibly realistic look at the work of Los Angeles Police department, shot in a pseudo-documentary style. Brian Taylor (Gyllenhaal) and Miguel Zavala (Michael Pena) are partners dealing with gang violence in the Latino community. The pair rubs some very bad people up the wrong way becoming targets.

Gyllenhaal and Pena have a very natural on screen chemistry which comes across during the long dialogue scenes in their patrol car giving the acting an improvisational feel. We also get the opportunity to see Gyllenhaal’s comedic side as the friends banter back and forth.

8 Jarhead – Anthony Swofford

Gyllenhaal as Anthony Swofford in Jarhead

Jarhead (Mendes, 2005, DE/US) tells the story of men whose gratification is constantly thwarted. Anthony Swofford and his unit train for action as snipers and get deployed as part of Operation Desert Shield but find that their services are in little demand. They are swallowed up and spat out by the Marine Corps, the traumatic effects of War swept under the carpet.

Based on the memoirs of the real-life vet Anthony Swofford, Gyllenhaal took on the challenge of representing his experiences. Gyllenhaal deftly conveys the futility of a modern War, where fire reigns from the sky, in a performance that is even more relevant today.

7 Moonlight Mile – Joe Nast

Moonlight MIle
Moonlight Mile stars Gyllenhaal as a young man balancing grief and expectation with new found love

Joe moves in with his dead fiancé’s parents as they collectively try to come to terms with her murder. Instead of attending his own wedding Joe finds himself at a funeral with a trial pending. He soon realizes that his ‘in-laws’ expect him to continue living the life they had planned with his girlfriend before her death.

In Moonlight Mile (Siberling, 2002, US) Gyllenhaal gives us a sensitive portrayal of a grieving young man trying to balance the welfare of his ‘in-laws’ with his need to rediscover his own direction. The events of the film are loosely based on writer/director Brad Siberling’s own life experiences.

6 Southpaw – Billy Hope

Gyllenhaal made an amazing physical transformation for Southpaw
Gyllenhaal made an amazing physical transformation for Southpaw

Successful professional boxer Billy Hope suffers from Marty McFly syndrome; he can’t back down from a challenge. His wife is killed during a post-match scrap, causing his life to spiral out of control and his daughter to be taken into care. He faces the biggest fight of his life; trying to win his daughter back.

As a film, Southpaw (Fuqua, 2015, US/HK) is a fairly predictable sports movie, but Gyllenhaal is sensational, giving a tour de force performance that makes it a worthwhile watch. Eminem was originally attached to play Hope, but Gyllenhaal’s ‘no half measures’ approach makes it hard to picture anyone else for the part.

5 Brokeback Mountain – Jack Twist

Brokeback Mountain
Brokeback Mountain saw Gyllenhaal team with Ledger in a touching and groundbreaking movie

Ennis (Heath Ledger) and Jack (Gyllenhaal) herd sheep in Wyoming. Alone in the wilderness, they develop a deep, loving relationship, but it’s the 60’s and their relationship challenges the social norm. Both men marry and have kids, yet are unable to forget their love.
Brokeback Mountain (Ang Lee, 2005, US) followed the conventions of a classic love story and in doing so it did more for LBGT equality than most movies.

Brokeback showed the world that; the love between two men was no different from love between a man and a woman. Ledger and Gyllenhaal’s touching performances helped to make homosexual relationships more accepted in mainstream culture.

4 Donnie Darko – Donnie Darko

Donnie Darko is a dark and strange movie
Donnie Darko captured the doubts of a generation and is one of Gyllenhaals best movie performances

Set in the 80’s but timelessly applicable, Darko is the story of Donnie, a teenage boy angry at a society that renders him powerless and afraid. His therapist is treating him for schizophrenia and he has visions of a giant rabbit named Frank who warns of the end of the world.

Donnie Darko (R. Kelly, 2001, US) was the film that defined a generation and Jake Gyllenhaal became the face of that generation. The future is coming for these kids and they don’t know if they have the power to change or influence it. Gyllenhaal makes Donnie smart and relatable, stopping his teen character from slipping into cliché.

3 Night Crawler – Louis Bloom

At the start of Night Crawler, (Gilroy, 2014, US) Louis Bloom lists his better qualities pitching for a job. He is refused, but later meets cameraman Joe Loder who is filming the victims of a car crash. Louis starts his own business filming accidents, his methods become increasingly unscrupulous in the pursuit of shock footage to sell to news channels.
Night Crawler is a parable for our times: hard work and honesty leave people at the bottom but a disregard for ethics is rewarded when it gets results.

The worst of society rises to the top. Gyllenhaal delivers a fascinating character study, using his physicality to reflect the psychology of the character.

2 Zodiac – Robert Graysmith

Zodiac sees Gyllenhaal's character become obsessed with solving the mystery of the killer
Zodiac sees Gyllenhaal’s character become obsessed with solving the mystery of the killer

Zodiac (Fincher, 2007, US) is a chilling police procedural thriller about the unsolved Zodiac case. Gyllenhaal is Robert Graysmith, a cartoonist for the San Francisco Chronicle who became obsessed with discovering the identity of the Zodiac killer, eventually writing the book that the film is based on.

Gyllenhaal clearly immersed himself in Graysmith’s life for the movie and he is perfect as a man who cannot deviate from the path he has started down, even at the cost of his family. Zodiac is heavy on information and could have become overloaded but Gyllenhaal’s enthusiasm pulls us down the rabbit hole with him.

1 Prisoners – Dt. Loki

Gyllenhaal play a detective trying to find some missing girls in Prisoners
Gyllenhaal play a detective trying to find some missing girls in Prisoners

Two young girls are kidnapped and Dt. Loki (Gyllenhaal) investigates their disappearance. Loki is meticulously observant and dedicated to finding the girls, but he doesn’t have a reassuring manner leading the girl’s parents to lose faith in him. Mr. Dover (Hugh Jackman) starts down a path of vigilante justice, interfering with Loki’s efforts.

In Prisoners (Villeneuve, 2013, US) Gyllenhaal once again plays a man with compulsive tendencies, obsessed with finding the truth. Gyllenhaal can really translate a character, he gives Loki a toothpick and a twitch; people don’t expect much of him and yet he is heroic. This is one the best Jake Gyllenhaal movies yet.

Do you agree with our list? What is your favorite Jake Gyllenhaal movie?

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