by ASH

He made his film debut (as Billy Crystal’s kid!) in City Slickers (1991), although we first noticed him in Donnie Darko (2001). As the titular character in Bubble Boy and the lovelorn admirer of Jennifer Aniston’s character in The Good Girl (2002), Jake Gyllenhaal was high on our radar in the early 2000s. Although all these characters are starkly different, Gyllenhaal, coming from a creative family with a director (dad), screenwriter (mum) and actress (Maggie Gyllenhaal), manages to always embody his onscreen characters effortlessly. He’s given us a handful of superb characters that should have gotten him the highest acting honour- the Oscar, but the golden statue has always escaped his grasp.

Here are four movies that Gyllenhaal should have totally gotten the Best Actor Oscar for.

Brokeback Mountain (2005)

This is a no brainer. As Jack Twist, caught in an accidental and illicit love affair with a fellow cowboy, Gyllenhaal gives the performance of his life. He’s grown from being the Bubble Boy to a full-blooded cowboy who finds unexpected love when confined in close quarters with fellow sheep herder on the aptly named Brokeback Mountain. Jack’s conflict and struggles are convincing, as is the love in his eyes whenever Ennis (Heath Ledger) shows up. Alas, he was nominated for an Oscar for Best Supporting Actor but lost to George Clooney for Syriana. The Academy definitely made a bad call here.

Brokeback Mountain

Nightcrawler (2014)

It started off quite normally, Louis Bloom is just a man struggling for work in Los Angeles. He accidentally stumbles upon a freelance source of work- crime journalism, and being the driven character he is, dives into the dangerous realm of nightcrawling with fervour.  But as he goes deeper, he blurs the line of ethics and in the process, gets more and more unhinged. Gyllenhaal’s transformation from a driven young man into a- for a lack of a better word- CREEP, is chilling. Towards the end of the movie, it’s not only the night that crawls, but Louis Bloom makes your skin crawl as well.


Southpaw (2015)

From the sinister Nightcrawler, Gyllenhaal does a 360 the next year, taking on Billy “The Great” Hope, a Middleweight Boxing Champion who seemingly has it all. Until he hits rock bottom. The character arch changes so much in the movie, but it’s nothing Gyllenhaal couldn’t handle. From the cocky, confident boxer to a down-and desperate washout, Gyllenhaal had us clenching our fists the whole time, rooting for Billy Hope to pick himself up. It’s appalling his performance was not even nominated for an Oscar.


Stronger (2017)

This time, Gyllenhaal portrays a real-life person- Boston Bombing survivor Jeff Bauman. To give a convincing performance, Gyllenhaal spent a great amount of time with the real Jeff Bauman, and the pair remains friends today. To prepare for his role, Gyllenhaal confined himself to a wheelchair initially, and observed how Bauman moves around with his stumps. He nailed the physical movements, but it’s the emotional ones that Gyllenhaal does much justice to Bauman. The post-traumatic stress, the guilt, the struggles all shown in Gyllenhaal’s huge expressive eyes. Gyllenhaal’s nuanced performance gives us a glimpse into Bauman’s life, and makes us almost forget that it was Gyllenhaal we’re watching, not Bauman himself. The sublime performance was once again, overlooked by The Academy.

Although Jake Gyllenhaal has yet to win an Academy Award, he’s won our hearts many times over.