Few actors have had stranger careers than Prisoners star Jake Gyllenhaal. After emerging on the scene with Donnie Darko (a movie that didn’t make this list, but you should definitely check out if you haven’t already), Gyllenhaal has experimented with a wide array of different personas before ultimately realizing that he may be best as a sort of character actor who can also play lead roles.
His career has included plenty of genuinely great movies, but these five really rise to the top, and are the ones that you should almost certainly check out first if you haven’t seen them already.
Zodiac (2007)
David Fincher tends to wear his actors down, and Gyllenhaal was no exception. Playing a cartoonist for the San Francisco Chronicle in the early 1970s as the Zodiac killer is murdering people in the Bay Area, Gyllenhaal stars as an obsessed man who is utterly fascinated by the killings.
As the movie unfolds, we come to understand that this movie is not about solving a case, but about living with the knowledge that the case may never be solved. Gyllenhaal is at his manic, quirky best here, giving a performance that perfectly underscores the perils of obsession, even if that obsession is a noble one.
Wildlife (2018)
The Batman‘s Paul Dano is still known best as an actor, but Wildlife is his directorial debut, and it’s proof that he could be excellent at that as well. The movie is told from the perspective of a young boy as his father, played by Gyllenhaal, leaves his family to fight a massive wildfire in Montana.
Gyllenhaal’s part here is firmly a supporting role, but his character’s struggles with providing for his family the way the film suggests he is supposed to provide some of the movie’s strongest moments. Elsewhere, Carey Mulligan puts on a show-stopping performance and proves definitively that she can be amazing in virtually any role.
Stronger (2017)
Perhaps one of the less well-known Gyllenhaal performances, Stronger stars the actor as Jeff Bauman, a real man who lost both of his legs during the Boston Marathon bombing. Jeff ultimately helps police identify one of the bombers, but the movie is really about his struggle to build a life for himself in the wake of the physical and emotional damage he’s experienced.
It’s one of Gyllenhaal’s best performances, and he’s matched perfectly by She-Hulk‘s Tatiana Maslany, one of the great unsung actors of her generation. Stronger may seem like a standard inspiring true story, but to the credit of everyone involved, it turns out to be much richer than that.
Brokeback Mountain (2005)
Brokeback Mountain was enormously successful, and enormously controversial when it was released in 2005. At the time, Heath Ledger’s performance was the one that most people spent time praising, but in the years since, many have come to appreciate that Ledger was only able to give his quieter, more reserved performance because of Gyllenhaal’s tremendous work as his primary scene partner.
Brokeback Mountain is delicate and heartbreaking, and the movie simply wouldn’t work if Gyllenhaal wasn’t so staggeringly great in a central role. Like many great Gyllenhaal performances, it’s still underrated by almost everyone and deserves reconsideration.
Nightcrawler (2014)
The most vaunted performance of his career to date, Gyllenhaal lost a bunch of weight to play Louis Bloom, an enterprising thief who stumbles into a career as a cameraman who arrives at grisly scenes as they unfold and captures real-time footage with as much detail as possible.
The movie’s twists and turns are both fun to watch and entirely predictable, and Gyllenhaal’s total commitment to the performance helps to sell the entire enterprise. Nightcrawler is an unsettling movie, and to his credit, Gyllenhaal’s performance is the most unsettling thing about it.
