The 15 Best Jake Gyllenhaal Movies Ranked

One of the rare child stars who became just as successful as an adult, Jake Gyllenhaal is one of the best actors working today. Gyllenhaal had a leg up getting his career started thanks to his Hollywood parents, director Stephen Gyllenhaal and screenwriter Naomi Foner, but established himself as a talented performer in his own right with a series of acclaimed performances throughout the '90s.

Gyllenhaal continues to deliver interesting turns in beloved films, earning his first Academy Award nomination for "Brokeback Mountain." After video game adaptation "Prince of Persia: The Sands of Time" became a box office bomb and earned Gyllenhaal criticism for whitewashing the character Prince Dastan, the actor apologized for taking the part. Gyllenhaal rebounded from that failure by taking on smaller projects from some of the industry's best directors. Although he likes the freedom of independent films, Gyllenhaal returned to tentpoles with a performance as the Marvel villain Mysterio in "Spider-Man: Far from Home." Next, he will star in Michael Bay's action-thriller "Ambulance" and the adaptation of Robert Kirkman's graphic novel "Oblivion Song."

Narrowing down Gyllenhaal's best work is a challenge, as he gives wildly different performances across many genres. Here are the 15 greatest Jake Gyllenhaal movies, ranked.

Gyllenhaal took on an interesting dual role in "Nocturnal Animals." The arthouse thriller follows reclusive novelist Edward (Gyllenhaal) as he briefly reunites with his estranged ex-wife Susan (Amy Adams), giving her a copy of his latest novel. Although "Nocturnal Animals" centers Susan's perspective, she's moved by his twisted book and discovers that many events in Edward's story mirror those from their actual marriage. Gyllenhaal, Adams, and the other people in the "real" world also play the characters in the book.

Edward's stand-in character is troubled father Tony, whose wife and daughter are kidnapped by a vile criminal (Aaron Taylor-Johnson). As Edward turns to a brutal local sheriff (Michael Shannon) for help, his soft personality becomes corrupted as they uncover a web of crime. Gyllenhaal subtly hints at Edward's pent-up anger towards Susan through the story, and expertly builds parallels between the movie's facts and its fiction.

"Brothers" features an unusually dark central performance from Tobey Maguire, who sheds his "boy next door" persona for a tortured performance as Afghanistan veteran Captain Sam Cahill. Gyllenhaal co-stars as his irresponsible brother Tommy, who is forced to take on added responsibility when Sam is presumed killed in action. Tommy feels like he needs to honor his brother's legacy by caring for his wife Grace (Natalie Portman) and her young children. Both Tommy and Grace are conflicted when romance blossoms, but they soon discover that, as friends, they're able to cope with Tommy's absence together.

The situation grows complex more when Tommy ends up alive; Gyllenhaal shows both Sam's relief and his shock at his brother's post-traumatic stress disorder. Gyllenhaal captures the anxiety of a changed man who isn't sure how to help, and he's tormented by Sam's fixation on Grace's infidelity. The complex process of healing is explored as Sam patiently allows Tommy to recount his experiences.

"End of Watch" is not your standard buddy cop movie. Shot by writer-director David Ayer as a documentary-style account by Gyllenhaal's character, officer Bryan Taylor, and his partner Miguel Zavala (Michael Pena), the film explores the everyday responsibilities that the two cops face on the job. The film is full of banter, and Gyllenhaal and Pena have terrific chemistry. They're believable as longtime partners who've grown accustomed to each other's quirks, and their playful arguments are the heart of the film.

Although he likes to lampoon Miguel for his eccentric family, Bryan begins to desire the life that his partner enjoys, and discusses his romantic encounters with Miguel. However, their responsibilities as police officers strain their relationships outside of the force. "End of Watch" never shies away from showing the danger of the job, and its gripping climax is emotional thanks largely to Gyllenhaal's nuanced performances.

"Wildlife" is an understated character drama that shows a crumbling marriage through the eyes of a child. Based on the classic novel by Robert Ford, "Wildlife" is the directorial debut of actor Paul Dano, who clearly understands how to get intimate performances out of his cast. Set in the Great Falls of Montana in the '60s, "Wildlife" follows a soft-hearted teenager named Joe (Ed Oxenbould) as he watches his parents Jerry (Gyllenhaal) and Jeanette (Carey Mulligan) grow apart over many years.

Jerry is a proud man who is embarrassed when he's fired from his job, and refuses to let his family down. Gyllenhaal captures Jerry's old-fashioned pride without making him haughty, and he's sensitive when interacting with his impressionable son. As Joe spends more and more time with his mother while his father is away looking for work, Gyllenhaal appears less frequently — but, like his character, he makes the most of his visits. It's heartbreaking to watch Gyllenhaal show affection for a son who has grown up in his absence.

"Stronger" depicts the aftermath of the Boston Marathon Bombing with graceful nuance, following a survivor as he struggles to cope with lasting trauma. Jeff Bauman (Gyllenhaal) had shown up at the race to support his ex-girlfriend Erin (Tatiana Maslany) and lost both of his legs in the explosion; not only must he learn to walk with prosthetic legs, but he talks to other survivors as he struggles with post-traumatic stress disorder.

"Stronger" excels by depicting Jeff as a well-intentioned but irresponsible character. While he's charming and entertaining, Jeff's relationship with Erin was in shambles before the tragic event took place. He's instantly sympathetic, but Jeff's debilitating injuries combined with his own initial refusal to improve put stress on both Erin and his family. Gyllenhaal shows Jeff's growth; he learns that he must put in the work to get better, and that he must take responsibility for the things he can control. His awareness grows as he meets other victims and learns that his story is just one of many.

"Stronger" shows the complexity of heroism. Jeff doesn't view himself as a hero, but he realizes how his recovery can be an inspiration to others who are struggling. In the film's most powerful scene, Gyllenhaal attends an emotional Boston Red Socks game and is overwhelmed when he sees how many lives his story has touched.

"Prisoners" is both a tightly wound investigative mystery and a thought-provoking morality tale. The film questions the lengths taken to rescue kidnapped children by both their families and law enforcement, and explores how the emotional stakes and responsibilities vary across different parties. Despite its 153-minute runtime, director Denis Villenueve keeps the tension high as the danger to the young lives grows more severe.

While celebrating Thanksgiving, an austere woodsman Keller Dover (Hugh Jackman) and his loving wife Grace (Maria Dover) are shocked when their daughter and her friend go missing. Detective Loki (Gyllenhaal) becomes involved in the case after finding a potential suspect, and eventually begins talking to both families. Loki is put in a challenging situation, and Gyllenhaal revels in the strain felt by the talented detective. Loki knows that the families are in indescribable pain, but he can't express empathy without violating his professionalism.

But Loki is a good detective, and Gyllenhaal captures Loki's expertise as well as his growing emotional investment in the case. He's both angry about and terrified of what Keller is capable of, and fears the consequences he will face if he takes the law into his own hands.

"Zodiac" is no standard serial killer film. The famously unsolved case of the Zodiac Killer haunted San Francisco Bay for decades, but rather than focusing on the depravity of the murders, director David Fincher chooses to track the obsessions of the men pursuing the criminal. Political cartoonist Robert Graysmith (Gyllenhaal) initially spars with veteran crime reporter Paul Avery (Robert Downey Jr.), but they ultimately begin working together to unravel the enigmatic messages that the killer sends to their newspaper. Graysmith's aptitude for solving puzzles sparks the interest of Inspector Dave Toschi (Mark Ruffalo), who suspects that an untraditional investigation may be the only way to track down the killer's identity.

As time passes, Graysmith's relationship with the case changes. He's not a crime reporter, but unsolved mysteries fascinate him. Gyllenhaal shows how Graysmith's good-natured curiosity transforms into obsession.

A heartfelt romance between Graysmith and Melanie (Chloe Sevigny) develops; Gyllenhaal and Sevigny have great chemistry as two earnest puzzle solvers, but the charming relationship is shattered as Graysmith refuses to set aside his fixations. It's heartbreaking to watch Graysmith slip into madness, but he's relatable enough that the climax, during which he's trapped with the presumed killer, is still a nail-biter.