Jake Gyllenhaal’s 10 Best Movies, According to Ranker

Over the years, Jake Gyllenhaal has involved himself in a wide range of different projects – starting off his mainstream career with biopic drama Donnie Darko, the actor soon moved towards studio dramas and action blockbusters, most recently in Michael Bay’s Ambulance.

Gyllenhaal has quickly come one of Hollywood’s most reliable and in-demand actors, bringing a certain level of commitment and charisma to every role that he adopts. He’s the kind of actor that completely disappears into his characters, often challenging himself with complex and unpredictable roles.

10 October Sky (1999)

October Sky is based on the true story of Homer Hickam, a coal miner’s son who finds himself fascinated by astronomy following the launch of Sputnik 1. His passion eventually leads him to become a NASA engineer, though his father does not approve of his career ambitions.

The film was one of Gyllenhaal’s first roles, and his portrayal of Hickam was heavily praised by critics upon release. Starring alongside Laura Dern, the actor quickly established himself as one of the strongest and most empathetic child actors out there.

9 Enemy (2013)

Denis Villeneuve’s mind-bending sci-fi adventure Enemy may have received a somewhat mixed response from both critics and audiences upon release, but it has since developed somewhat of a cult-classic status thanks to its inventive and original storyline and confoundingly complex narrative.

Gyllenhaal actually provides two performances in Enemy – one as a mild-mannered college professor, and one as his look-alike actor that falls victim to the professor’s obsession and dependence. It’s this complex performance that makes Enemy one of Gyllenhaal’s best films to date.

8 Donnie Darko (2001)

Perhaps the film that really kicked off Jake Gyllenhaal’s career, Donnie Darko has since become one of the most beloved and admired sci-fi classics of the modern era. The film follows Donnie as he navigates the fallout of a freak accident, discovering hidden truths about time, existence, and (maybe) parallel universes?

The fact that nobody quite knows the truth of Donnie Darko is one of the things that makes it so special and unusual. The entire film has an intriguing but unsettling atmosphere throughout, as though challenging the viewer to understand its complex themes.

7 Wildlife (2018)

Directed by long-time actor Paul Dano, Wildlife follows a young boy forced to keep his parents’ marriage together after his mother falls in love with another man. It’s an extremely emotional and thoughtful drama, which is tightly bound by both Jake Gyllenhaal’s and Carey Mulligan’s expert performances.

Wildlife is one of the most impressive and underrated debuts from an actor-turned-director, mostly thanks to Dano’s impressive craft behind the camera. Both with the direction and the screenplay, Dano clearly understands what makes his characters tick and really promotes this through his actors.

6 End of Watch (2012)

End of Watch stars both Jake Gyllenhaal and Michael Pena as two LAPD officers who work in Southern Los Angeles. The film follows their daily lives as they deal with small-time criminals, personal relationships, and inner conflicts. Despite being a crime thriller, End of Watch focuses primarily on the partnership between Gyllenhaal and Pena’s characters.

Gyllenhaal seems to thrive in these kinds of intense roles, where he gets to showcase his wide range of emotions and expressions. He plays off of his co-stars really well and adds a whole new level of compassion and empathy to writer/director David Ayer’s already-compelling script.

5 Zodiac (2007)

Directed by crime thriller auteur David Fincher, Zodiac follows the San Francisco Police Department’s attempts to track down and capture the Zodiac Killer. Gyllenhaal plays a young cartoonist who becomes obsessed with the case, throwing himself directly into the crossfire by doing so.

Since the film’s release, Zodiac has become considered by many to be one of Fincher’s best films – particularly thanks to its precise and intricate screenplay, which effectively navigates the dangers of obsession and fixation on crime. It does everything that Fincher has become so admired for, boasting three fantastic performances as a bonus.

4 Southpaw (2015)

In Southpaw, Jake Gyllenhaal plays Billy “The Great” Hope, the middleweight boxing champion who soon finds himself hitting rock bottom when tragedy strikes and he loses his family and his home. The film follows Hope’s attempts to reclaim the life he once had with the help of his coach Tick Willis.

Many often cite Southpaw as one of Gyllenhaal’s best performances, since he’s given plenty of destructive and emotional material to work with. Billy Hope can’t have been an easy character to play, but Gyllenhaal manages to make it seem effortless.

3 Nightcrawler (2014)

Louis Bloom is undoubtedly one of the most interesting and unique characters that Jake Gyllenhaal has ever played, not least because of his ability to switch personalities disarmingly quickly. He’s a freelance cameraman on the search for crimes to record in Los Angeles, but his hobby soon turns into a dark obsession.

Nightcrawler doesn’t just feature one of Gyllenhaal’s best and most iconic performances, but it’s also a fantastically crafted movie in itself. It boasts a thrilling story, a unique script, and inspired visuals from director Dan Gilroy, which all come together for one of the most compelling thrillers of the 2010s.

2 Prisoners (2013)

The second movie on this list from visionary director Denis Villeneuve, Prisoners is an exciting crime thriller with a dark twist. The film follows Hugh Jackman’s character, who is forced to take the search for his missing daughter into his own hands when Gyllenhaal’s Detective Loki is unable to make any progress.

What makes Prisoners so endlessly watchable is just how thrilling and gripping the story is. It’s never predictable, but rather takes sharp twists and turns throughout to keep the audience on their toes and allow for some rich and thoughtful exploration of its characters.

1 Nocturnal Animals (2016)

Nocturnal Animals is based on the 1993 novel Tony and Susan by Austin Wright and centers around a divorced art gallery owner who begins to spot suspicious similarities to her own life in a new novel written by her ex-husband. It’s a fantastic neo-noir adventure that grips the audience from the very first frame and encapsulates you in this dark and stylish world.

Both Amy Adams and Jake Gyllenhaal both provide exceptional lead performances, but the real star of Tom Ford’s drama is the craft behind the screen. The film’s ultra-precise screenplay and inspired direction create a unique and interesting atmosphere that gives every character space to breathe and develop throughout the course of the narrative, which allows the whole film to come together into something extremely gripping and exciting.

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