What are the best Jake Gyllenhaal performances? From his baby-faced first outing on the silver screen in Ron Underwood’s City Slickers (1991), through to his latest movie, the Michael Bay action-thriller Ambulance, Jake Gyllenhaal has given us some terrific and truly unforgettable performances through the years. But which of his many movie roles are the best?

Nightcrawler (2014)

Jake Gyllenhaal gives an impeccable all-round performance in Dan Gilroy’s directorial debut, in what is one of the most criminal Oscars snubs of all time. He plays Louis Bloom, a freelance journalist constantly in search of the latest big story, be it a car crash or a multiple homicide, with the intention of recording camera footage and selling it to the highest-bidding news outlet. Lou Bloom is not your average Joe however.

Mercilessly, he works his way up the ladder, leaving his peers in his wake, often with tragic consequences. Bloom is such a divisive character, leaving the audience questioning whether to empathise with him or despise him for his ruthless, brutal methods. He is a clever and amusing man, but is capable of the most dark and menacing behaviour you would expect from a villain.

Jake Gyllenhaal as Donnie Darko

Donnie Darko (2001)

A young Jake Gyllenhaal stars as the titular character, a messed up teen with schizophrenia and an imaginary friend in the form of a giant bunny rabbit who can travel through time. Sounds ridiculous, but this is one of the most engaging, thought-provoking and enigmatic films you will ever see, and it even has a fantastic soundtrack to boot; a must-watch for fans of the psychological-thriller genre

Jake Gyllenhaal as Detective Loki in Prisoners

Prisoners (2013)

While Jake Gyllenhaal doesn’t quite hit the heights of a Lou Bloom or a Donnie Darko here, his Detective Loki is certainly very cool, likeable, and he provides a great hero figure. It’s a brooding, charismatic display, from a character who for the most part looks to show very little emotion, yet upon closer inspection, we see that his job affects him deeply. It’s all in the details, like the excessive blinking and an underlying need for control.

Prisoners is one of the first films to put its director, Denis Villeneuve on the map, and is easily one of the best films of the last decade.

Enemy (2013)

Here is Jake Gyllenhaal at his versatile, intense best. As Adam, he is brilliantly authentic in his portrayal of a troubled, confused character but is far too hesitant and suspicious rather prematurely. There is no denying however, that his latter scenes with Helen are some of the most powerful and emotive of the whole film.

It is as the aggressive, domineering, rather detestable Anthony though, where Gyllenhaal really flourishes. The amalgamation of the two characters in Enemy resonates with his role as the titular character in Donnie Darko, an uncanny projection of a future Donnie, a 30-something schizophrenic with plenty more issues.

Nocturnal Animals (2016)

Jake Gyllenhaal shows incredible range in his dual role in Tom Ford’s Nocturnal Animals. Gyllenhall plays Edward Sheffield, the estranged ex-husband of Amy Adams’ character, and in the novel he portrays Tony Hastings, a man on vacation with his family before they’re forced off the road by a gang. Two very different roles in the film but, of course, Jake Gyllenhaal absolutely nails both and ultimately breaking our hearts in the process as Edward’s novel becomes much darker than originally anticipated.

Brokeback Mountain (2005)

A far cry from the more unhinged and unpredictable performances we have seen so far in this list, with a tender and heartfelt role in this beautiful romance movie. Starring opposite the late, great, Heath Ledger, Gyllenhaal offers an incredibly nuanced and emotional performance as Jack Twist. Jake Gyllenhaal was Oscar-nominated for his role here, and deservedly so.

Wildlife (2018)

Continuing the trend of a slightly more mellow Gyllenhaal, is his turn in Wildlife, the directorial debut of The Batman star Paul Dano. This is arguably one of Gyllenhaal’s most mature and convincing performances, with such subtle yet effective character work making this one of his more underrated performances to date.

Zodiac (2007)

Back in his more natural habitat of a dark, psychological thriller, Jake Gyllenhaal lines up in an all-star cast for David Fincher‘s brooding depiction of the infamous Zodiac Killer. Alongside Robert Downey Jr, Mark Ruffalo, and Chloe Sevigny, Gyllenhaal holds his own as the protagonist in this twisted and terrifying movie.

Jake Gyllenhaal as Mysterio in Spider-Man: Far From Home (Credit: Disney)

Spider-Man: Far From Home (2019)

It was somewhat surprising to see Jake Gyllenhaal jump into the world of comic book movies, when he joined the MCU as Spider-Man villain Mysterio. However, credit where credit’s due, Gyllenhaal dives in head first here and looks like he’s having a hell of a lot of fun in the role. It remains to be seen whether we will ever see him return to the MCU, but we certainly hope Kevin Feige finds a way!

Okja (2017)

Of all the roles on this list, you wouldn’t imagine that Jake Gyllenhaal is at his most bizarre and deranged in this cute family movie, but that’s the beauty of this incredible performer. Directed by Bong Joon-ho, this fantasy movie carries an important message and some truly heartbreaking moments, but Gyllenhaal’s eccentric performance as Johnny Wilcox is definitely one of the most memorable aspects of Okja.

There we go, those are the 10 best Jake Gyllenhaal performances in his fine filmography so far. If you’re looking to explore more actors and their best roles, check out our list of the best Oscar Isaac performances.