The movies Jake Gyllenhaal is most proud of

Few actors in modern Hollywood are quite as underrated as Jake Gyllenhaal, having been nominated for just one Academy Award over the course of his 32-year career despite being deserving of about three or four. Having worked with the likes of Ang Lee and Denis Villeneuve while also occupying a space in the Marvel Cinematic Universe, Gyllenhaal is a truly versatile acting talent.

Rising to popularity back in the early 1990s, appearing in a number of somewhat random movie roles, including Joe Johnston’s 1999 film October Sky, it wasn’t until the new millennium that Gyllenhaal would find proper success. Indeed, the star only needed the one film, starring in Richard Kelly’s Donnie Darko, where he earned critical and commercial plaudits.

After a few further commercial hits, such as the disaster flick The Day After Tomorrow, Gyllenhaal then went on to earn his first Oscar nomination, gaining rave reviews for his performance in Ang Lee’s Brokeback Mountain. In the years that followed, he collaborated with David Fincher for Zodiac, Dan Gilroy for Nightcrawler, then entered the MCU as the villain Mysterio in Spider-Man: Far from Home.

But, just like many actors, there is only a small bunch of films that Gyllenhaal says that he’s most proud of.

“Auditioning at a young age, I was like, ‘What are these movies about?’ Like my high school experience wasn’t like this at all,” he told Entertainment Weekly, “Then Donnie Darko came up, and I was like, ‘oh this feels like my high school’, so that gives you any insight into who I am and how I pick roles”. 

Playing the title character, a young, troubled teenager, Donnie Darko tells the story of Donnie, who is plagued by visions after a bizarre accident, including the hallucination that a large humanoid bunny rabbit is following him. Adored by a loyal fanbase, the movie starred the likes of Jena Malone, Mary McDonnell, Holmes Osborne, Maggie Gyllenhaal and Patrick Swayze.

Continuing, he goes on to reference October Sky, the movie he made shortly before Donnie Darko, “I was super young when I made October Sky…and then also Donnie Darko, so those are different sides of me…I believe in hope, I believe in love, I believe that the human mind is really complicated, so yeah, I think Donnie Darko, to me, is one of my favourite movies I’ve made and what I’m most proud of because it does sort of define, not the way I look at the world literally, but there are a lot of things in there that I believe about the world”.

Take a look at Gyllenhaal’s full conversation with Entertainment Weekly below.

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