10.Brothers(2009)
Brothersis a psychological drama film about a soldier who was presumed dead, but returns home from being a prisoner-of-war and deals with PTSD as he tries to reintegrate back into society.
Jake Gyllenhaal plays the brother to that soldier (played by Tobey Maguire), and the two have such great on-screen chemistry that they successfully deliver an emotionally heavy performance that’s deserving of the content matter at hand.
9.Southpaw(2015)
Southpawis a sports drama movie written by Kurt Sutter (the mind behindSons of Anarchy) about a lost boxer who’s trying to find his way back in life after his wife dies and his daughter is taken from him.
While the movie itself is a love-it-or-hate-it affair depending on your tolerance for sports movie tropes, Jake Gyllenhaal’s performance—along with the performance of his young co-star Oona Laurence—is outstanding in a role that’s outside his usual ones.
Related:The best boxing movies ever
8.Source Code(2011)
Source Codeis a sci-fi mystery thriller movie where Jake Gyllenhaal plays Captain Stevens, who repeatedly enters a computer simulation to find the bomber of a commuter train before it explodes in 8 minutes.
There are lots of twists and turns in this action movie, especially when it comes to the time-loop elements, but it’s Gyllenhaal’s expressive performance that keeps you hooked all the way through.Source Codeis an underrated sci-fi thriller that deserves more love!
Related:The best movies with time travel
7.End of Watch(2012)
End of Watchfollows two LAPD officers, played by Jake Gyllenhaal and Michael Pena, as they live their lives—tending to their daily police work, maintaining order in their South LA district, all while supporting each other and dealing with their personal relationships.
Unlike most police-oriented movies,End of Watcheschews the usual “corrupt cop” tropes in favor of a more realistic and down-to-earth portrayal of honest cop work. Gyllenhaal puts in an incredible performance all the way to the end.
Related:The best buddy cop movies on Netflix
6.Brokeback Mountain(2005)
Brokeback Mountainis a groundbreaking film in many ways, and the accolades deserve to be shared all around—from Ang Lee’s direction to the short story it was based on—but it’s all grounded on the vulnerable performances by both Jake Gyllenhaal and Heath Ledger.
They play two American cowboys who meet when they’re hired to herd sheep for a summer. During their time alone, they develop a complex relationship with each other that grows even more complicated when they part ways at summer’s end.
Related:The Best Indie Movies of the 2000s, Ranked
5.Zodiac(2007)
Zodiacis a mystery thriller film—directed by the king of thrillers, David Fincher—based on the true story of the Zodiac Killer, a serial killer from the 1960s and 1970s who remains unknown to this day.
While the film focuses more on those who are trying to solve the mystery than the one commiting the crimes, it’s as intense and suspenseful as any action-packed thriller. Just don’t go into it expecting a gruesomeness on the level ofSe7en.
Related:The best David Fincher movies
4.October Sky(1999)
October Skyis a coming-of-age drama that tells the story of a coal miner’s son who wants to become a NASA engineer after watching the launch of the Sputnik 1 satellite. His father doesn’t want that for him, which puts a lot of stress on their relationship.
It’s interesting that Gyllenhaal was only 19 years old at the time of this film, proving that he’s had the ability to deliver strong performances since his youth.October Skyis earnest, inspirational, and effective—and a lot of that comes from what Gyllenhaal puts into it.
Related:The best teen movies about coming of age
3.Nightcrawler(2014)
Nightcrawleris a neo-noir thriller movie about a man who chases violent events at night to record with his camcorder, so he can sell his footage to TV news stations. He’ll go to whatever lengths necessary to snag the shots he needs.
If you want to see Jake Gyllenhaal in his most unsettling performance ever, this is the movie to watch. It’s dark, it’s thought-provoking, and it’s memorable—mainly because of Gyllenhaal’s frighteningly realistic portrayal of a sociopath with no conscience.
2.Donnie Darko(2001)
In one of his most iconic roles, Jake Gyllenhaal plays a troubled teenager who’s manipulated into committing crimes by an imaginary man in a rabbit costume. That rabbit-man also tells him that the world is going to end in 28 days.
Donnie Darkoisn’t an easy movie to watch, but it’s a fascinating one for all the strange, unsettling, and unique ideas it explores. Even if you don’t love it, you have to respect it—along with Gyllenhaal’s convincing performance as the unhinged Donnie Darko.
Related:The best movies with personality disorders
1.Prisoners(2013)
Prisonersis a suspense thriller film about two fathers, played by Jake Gyllenhaal and Hugh Jackman, who vow to find and rescue their abducted young daughters. When it seems like the police won’t do their jobs, they take matters into their own hands.
This movie has a deep sense of grounding in reality, which makes it that much darker, more dreadful, and more disturbing than it might otherwise be. Gyllenhaal and Jackman are both amazing, working to elevate each other’s performances to world-class levels.
