Before ‘Southpaw’: Jake Gyllenhaal’s 5 Best Movie Roles

When Southpaw hits theaters on July 24, audiences around the country will see a very new side of Jake Gyllenhaal. The 34 year-old actor plays Billy Hope, a boxer who fights his way back from tragedy to gain custody of his daughter after his life spirals out of control following his wife’s murder. Though the movie doesn’t hit theaters for a few weeks, it’s already gained major buzz, partly because of the lead actor’s tremendous physical transformation for the role. He adopted an extreme workout regime and gained 15 pounds of muscle so he looked convincing as a boxer on screen. But this isn’t the first time Gyllenhaal has gone to extreme measures for a role – nor the first that he’s received critical acclaim. Growing up in a show business family, he played bit parts as a child before pursuing a full-time acting career over a decade ago. Since then, he’s made a name for himself, working steadily in some of the most well-received and memorable films of the last 20 years. He’s never shied away from controversial material or challenging roles, which has given him a reputation for being one of the most unpredictable and riveting actors of his generation. Though it’s hard to narrow it down, here are five of his most unforgettable performances.

Jake Gyllenhaal in 'October Sky.'
Source: Universal Studios

1. Homer Hickam – October Sky

It’s not easy for an 18-year-old to carry a film. But in October Sky, Jake Gyllenhaal did just that, emerging as a breakout Hollywood star and holding his own against Award-winners like Laura Dern and Chris Cooper. October Sky is based on the true story of Homer Hickam Jr., a NASA engineer who grew up in the heart of coal mining West Virginia. Gyllenhaal stars as Homer Hickam, whose insatiable interest in Sputnik and rocketry fuels him to take huge risks and achieve his dreams. Gyllenhaal is nothing short of fantastic in October Sky. He perfectly captures the inner turmoil Hickam felt at being drawn toward science while he’s expected to follow in his miner father’s footsteps. His tense scenes with Cooper, who plays his disapproving father, are devastatingly realistic, and a highlight of the entire film. With equal gusto, he plays Hickam’s idealism and quiet intelligence with a wisdom far beyond his young years.

Jake Gyllenhaal and Jena Malone in 'Donnie Darko.'
Source: Flower Films

2. Donnie – Donnie Darko

This eerie dark comedy has become a cult classic in the years since its release. But so much of what makes Donnie Darko work, about a young man who has visions of a sinister figure telling him about the end of the world, is Jake Gyllenhaal’s masterful performance as the titular character. He’s a little bit weird from the get go, but gets progressively weirder as the world around him starts to tilt on its head. Gyllenhaal manages to fit right into the surreal aesthetic, expressing Donnie’s psychological troubles without ever alienating you.

Heath Ledger and Jake Gyllenhaal in 'Brokeback Mountain.'
Source: River Road Entertainment

3. Jack Swift — Brokeback Mountain

It was one of the most applauded and controversial films of the early 2000s, but Brokeback Mountain wasn’t just lauded for its brave portrayal of two men falling in love. Critics agreed almost universally that the two lead actors, Heath Ledger and Jake Gyllenhaal, made the film worth watching. Gyllenhaal plays Jack Swift, a cowboy turned salesman who’s torn between the family life he thinks he should live and the man he loves. He had the challenge of playing Jack over the course of a few decades – and he did an incredible job of showing the toll of aging, taking his character from an exuberant young man to one defeated by life and his secrets. Jake Gyllenhaal earned his first Oscar nomination for his performance as Jack Swift.

Jake Gyllenhaal and Hugh Jackman in 'Prisoners.'
Source: Alcon Entertainment

4. Detective Loki — Prisoners

Jake Gyllenhaal continued the trend of tackling difficult material with this 2013 crime thriller. In Prisoners, he plays Detective Loki, who doggedly goes after the truth when two young girls go missing on Thanksgiving Day. The film’s subject matter is, without a doubt, disturbing – it originally received an NC-17 rating for its graphic depiction of violence. While some critics found the content too extreme, no one could deny Gyllenhaal’s performance as Loki, which The Atlantic‘s Christopher Orr called “too powerful to ignore.” His obsession with solving the crime before him is so relentless, you can’t help but become invested in learning the truth, too, even though you know it may be too much to bear.

Nightcrawler - Jake Gyllenhaal
Source: Open Road Films

5. Lou Bloom — Nightcrawler

Lou Bloom isn’t just Jake Gyllenhaal’s creepiest role to date – he’s one of the creepiest characters on film, period. Nightcrawler follows Lou as he tries to kick start a career as a crime scene videographer for Los Angeles late night news shows. But he’s got at least a couple of screws loose, and as he gets deeper into the world of LA’s seediest streets, he starts to become completely unhinged in his drive to get the breaking story. Gyllenhaal lost 30 pounds to give Bloom an emaciated look that adds to his creepy, almost other-worldly aura. But it’s his intensity, not his physical transformation, that really make his performance so noteworthy.

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