Jake Gyllenhaal’s Best Performances, Ranked

Jake Gyllenhaal is a movie star with an impressive range of talent. His performances have spanned several genres, and he is unquestionably one of the greatest actors currently working. Gyllenhaal has the charisma, physicality, and emotional range to steal every scene he is in. It helps that Gyllenhaal comes from a family of professional talent, being the son of director Stephen Gyllenhaal and screenwriter Naomi Foner. His sister, Maggie Gyllenhaal, is an equally accomplished star. He is certainly Hollywood royalty, but he has endured because he is a talented actor.

Updated Jan. 27, 2024: This article has been updated with more information about Jake Gyllenhaal’s best performances, as well as useful features.

Gyllenhaal has seemingly done it all, having come a long way from his first major movie in the 1991 hit City Slickers. Gyllenhaal had a very busy 2022 as he starred in Michael Bay’s Ambulance and lent his voice to the Disney animated film Strange World. In 2023, he starred in Guy Ritchie’s The Covenant, and is currently set to star in a remake of Road House. He will also star in the Apple TV+ miniseries, Presumed Innocent, by Big Little Lies creator David E. Kelley. With that in mind, here are Jake Gyllenhaal’s best performances.

11 Nocturnal Animals (2016)

In Tom Ford’s Nocturnal Animals, Gyllenhaal stars alongside Amy Adams as Edward Sheffield and Susan Morrow, respectively. The two were a married couple at one point, eventually splitting apart and remaining distant for decades. When Morrow is given a manuscript written by Sheffield in order to get her opinion of its quality, she finds a strange sense of déjà vu within the story’s contents.

Gyllenhaal Plays Both Sides in Nocturnal Animals

Gyllenhaal gives a heartbreaking performance filled with rage and fury. The fact that he could play dual roles here, both playing a character in the novel and the real-life Edward Sheffeld with such ease, only adds to his sheer talent. Although the audience roots for Gyllenhaal’s character, there is also frustration stemming from his inability to save his family. The audience is then given the chance to see him work endlessly to avenge his wife and daughter. Casting Gyllenhaal in both roles also makes for an interesting commentary on how main characters can be utilized by authors to explore facets of themselves.

Buy or Rent Nocturnal Animals on Prime Video

10 Love & Other Drugs (2010)

In Love & Other Drugs, Gyllenhaal plays Jamie Randall, a womanizer whose immature antics get him fired from his job. Luckily for him, his charm gets him a new job as a pharmacuetical sales person. But things get complicated when he has to choose between that career and Maggie (Anne Hathaway), a woman with Parkinson’s disease he fell in love with while on the job.

Love & Other Drugs Is Carried by Gyllenhaal and Hathaway

The setup of this romantic comedy isn’t all too impressive or unique, but Gyllenhaal and Hathaway both play their characters so well that it brings the film to life. The two talented actors play off of each other to create magnetic chemistry and don’t miss a beat, which can often be the undoing of romantic movies if handled incorrectly. It may not be Gyllenhaal’s most popular movie, but it’s certainly one that demonstrates his broader range in a more lighthearted setting.

Buy or Rent Love & Other Drugs on Apple TV

9 Demolition (2016)

In acclaimed filmmaker Jean-Marc Vallee’s Demolition, Gyllenhaal plays Davis, an investment banker, who begins to deconstruct his life after the death of his wife. Shortly after the incident, when Davis is pushed over the edge after a vending machine malfunctions, the resulting complaint to customer service puts him on the line with Karen Moreno (Naomi Watts). The two of them are unaware that such an innocuous conversation may lead to something greater.

Gyllenhaal Grieves in Demolition

Gyllenhaal’s character is charismatic, and it is fascinating to see his methods of dealing with grief. He gives a fantastic performance with a good blend of comedy and drama, convincingly displaying moments of heartbreak and regret. At the same time, Davis acts as a father figure for a young boy (Judah Lewis), rounding out his character into something more fully developed.

Buy or Rent Demolition on Prime Video

8 Stronger (2017)

Gyllenhaal gives a compelling dramatic performance in Stronger, telling the true story of Jeff Bauman, who tragically lost his legs in the Boston Marathon Bombing. Released in 2017, David Gordon Green directed this feature after previously rising to fame with films like Pineapple Express and The Sitter, later going on to direct the modern Halloween trilogy only a year later. Gyllenhaal stars alongside Tatiana Maslany, Miranda Richardson, Carlos Sanz, and Clancy Brown

Gyllenhaal Physically Transforms Himself in Stronger

Gyllenhaal effectively transforms into Bauman and conveys the pain and sorrow that he felt during this time. Gyllenhaal balances this dark feeling with internal optimism, showing us how to overcome even the most tragic situations. The film, overall, is a great story of strength and perseverance. Gyllenhaal also proves his ability to transform into a character physically by nailing a consistent Boston accent, while simultaneously playing a character who was years younger than him at the time.

Stream Stronger on Netflix

7 Spider-Man: Far From Home (2019)

Gyllenhaal played the main villain, Mysterio, in Spider-Man: Far From Home, the final chapter in the MCU’s Infinity Saga. Mysterio’s real name is Quentin Beck, a former employee of Stark Industries, who wants to become the new face of superheroes after Tony Stark made a joke out of his life’s work. Gyllenhaal famously almost took over the role of Spider-Man from Tobey Maguire for Spider-Man 2, and while that did not work out, he eventually found himself in the wall crawler’s universe.

Gyllenhaal Hams It up in Far From Home

What makes Mysterio such a great performance from Gyllenhaal is it allows him to play two very different roles. Early in the movie, he is made out to be a normal hero, and Gyllenhaal gets to put on the charm he displayed in films like Love and Other Drugs and Brokeback Mountain. Once the twist is revealed, and he shows himself as the true villain, he is unhinged and chewing the scenery, similar to his iconic performances Nightcrawler or Velvet Buzzsaw. Spider-Man: Far From Home showed two sides of Gyllenhaal at his best, and he has left a lasting impression on both the character and the franchise.

Stream Spider-Man: Far From Home on Disney+

6 Zodiac (2007)

Zodiac

Release Date

March 2, 2007

David Fincher’s Zodiac tells the story of the investigation of the infamous Zodiac murders. Gyllenhaal plays Robert Graysmith, a cartoonist who becomes obsessed with the investigation, eventually contributing heavily to the case’s investigation. Mark Ruffalo, Robert Downey Jr., Brian Cox, and Dermot Mulroney star alongside Gyllenhaal in this intense thriller, making his stand-out performance even more impressive.

Zodiac Put Gyllenhaal on the Map

His performance is subtle and carried out quite well as a mild-mannered and innocent character, proving that he can play a wide variety of roles. At the same time, Gyllenhaal has great chemistry with his fellow co-stars, including Robert Downey Jr. and Chloë Sevigny. Zodiac is often considered one of the greatest movies of the 2000s, and a highlight for director David Fincher. While Gyllenhaal had been making a name for himself as a dramatic actor, Zodiac truly made him a name to watch out for, and his career only took off from there.

Buy or Rent Zodiac on Prime Video

5 Donnie Darko (2001)

Donnie Darko

Release Date

October 26, 2001

Director

Richard Kelly

Donnie Darko was one of Gyllenhaal’s earlier films, and it has since become a cult classic. Gyllenhaal plays the titular character who is having terrifying visions, including those featuring a monstrous rabbit named Frank. As a result, he is convinced to start carrying out several crimes. An indie darling, director and writer Richard Kelly would be elevated to stardom after the film’s release, with Gyllenhaal starring alongside Jena Malone, Maggie Gyllenhaal, Drew Barrymore, and Mary McDonnell.

Donnie Darko Was an Important Stepping Stone

Gyllenhaal gave a disturbing and convincing performance as a troubled teenager and proved that he had a broad acting range early in his career. At the same time, Gyllenhaal brings us into the mind of a teenager battling mental illness while also showing him as just a child, portraying a fully three-dimensional character in one of his earliest roles. You could argue that this would be an important stepping stone for Gyllenhaal’s future career in film.

Stream Donnie Darko on Shudder

4 Jarhead (2005)

Jarhead

Release Date

November 4, 2005

In Sam Mendes’ Jarhead, Gyllenhaal completely embodies the torment and pain that can come along with being enlisted in the military. Based on the memoirs originally written by Anthony Swofford, Jarhead sees Gyllenhaal playing Swofford in the middle of the Persian Gulf War. As part of the Marine Corps, Swofford and his friends find themselves battling both a foreign enemy and their own boiling tensions in the desert sun. Though the film saw mixed critical reception at the time of its release, some now consider it to be an underrated war movie.

Gyllenhaal’s Jarhead Is a Dramatic Powerhouse

Gyllenhaal gives a powerful performance with several great dramatic moments. He conveys the brutal pain and frustration that soldiers feel while at war. It’s appropriate, given that the film is a deep dive into the mind of a soldier. Gyllenhaall delivers an extremely convincing performance, showing you the emotional toll on an individual living in such a disturbing environment, reminding us of a painful conflict that will haunt us for generations.

Buy or Rent Jarhead on Apple TV

3 Prisoners (2013)

In Denis Villeneuve’s Prisoners, Gyllenhaal plays a tough and intelligent detective, Loki, who is determined to find two missing girls in the middle of Pennsylvania. Hugh Jackman stars alongside Gyllenhaal as Keller Dover, with Villeneuve combining the two actors in a spine-tingling thriller. The film as a whole would later go on to be nominated for Best Cinematography at the Academy Awards.

Gyllenhaal Plays a Tense Detective

Through his gritty emotion, Gyllenhaal creates a character who obviously has a dark past and has seen many disturbing things throughout his career. During all the action, Gyllenhaal incorporates a nervous tick throughout his performance, proving his excellence at adding layers of authenticity to his on-screen characters. Gyllenhaal would later win Best Supporting Actor at the Hollywood Film Festival for his performance.

Buy or Rent Prisoners on Prime Video

Related

12 Underrated Jake Gyllenhaal Movies, Ranked

From high-quality thrillers to well-made war dramas, these feature films with Jake Gyllenhaal never quite got the love they deserved. Now’s the time.

2 Brokeback Mountain (2005)

Gyllenhaal gives one of his greatest performances to date in Brokeback Mountain. Gyllenhaal stars as Jack Twist, a cowboy who falls in love with Ennis Del Mar, brilliantly played by Heath Ledger. Released in 2005, Brokeback Mountain would become an iconic piece of cinema for a time, not only due to its groundbreaking story, but for the incredible chemistry shared between Gyllenhaal and Ledger throughout the film’s numerous twists and turns.

Gyllenhaal Is Iconic in Brokeback Mountain

Gyllenhaal’s performance in Brokeback Mountain shows us the anguish and frustration he has loving Ennis in a world that will never accept them. Jack longs for a life with Ennis, and Gyllenhaal completely showcases a man living a life of quiet desperation. His performance only intensifies as the film continues, giving the story a level of emotional depth that struck the hearts and minds of audiences during its initial premiere. Gyllenhaal earned an Academy Award nomination for Best Supporting Actor for his performance here.

Buy or Rent Brokeback Mountain on Prime Video

1 Nightcrawler (2014)

Gyllenhaal gives possibly his best performance of all time in Nightcrawler as Lou Bloom, a man driven to become a successful video journalist. Unfortunately, after failing to find success via traditional means, Bloom takes the life of being a “stringer” — a freelance photographer with a particular specialty. Bloom spends his nights filming tragic news stories for cash, willing to do anything to get a good story.

Nightcrawler Has Gyllenhaal’s Best Performance

Gyllenhaal plays a character who is extremely charismatic but lacking in empathy. His dark portrayal of Bloom shows us an evil character who is satisfied with killing in exchange for success, something that not many people can fathom doing, much less convincingly portray. Many were rightfully frustrated when Gyllenhaal wasn’t nominated for Best Actor at the Academy Awards for his role in Nightcrawler, as the sheer level of intensity and passion put into every movement and expression has to be seen to be believed. Nightcrawler is a smart look into the ruthlessness of capitalism, giving us what truly has to be Gyllenhaal’s best performance to date.

Buy or Rent Nightcrawler on Apple TV

Now that you’ve seen some of Jake Gyllenhaal’s best performances, be sure to check out his latest role in Prime Video’s Road House, a streaming exclusive slated to premiere on Mar. 21, 2024. Check out the trailer below: