Jake Gyllenhaal's 15 Best Films, From 'Brokeback Mountain' to 'Nocturnal Animals'

In addition to being the spokesperson for Prada and Ginori 1735, the new cover star of L'OFFICIEL Hommes Italia Jake Gyllenhaal is one of Hollywood's most beloved actors, often praised for his versatility and attention-capturing performances. Over the years he has demonstrated, through a wide range of roles, that he knows how to tackle even the most difficult parts, and Gyllenhaal's ability to deliver compelling performances across different genres has turned him into one of Hollywood's most respected and acclaimed actors. His stellar performances have resulted in critical recognition, including numerous prestigious Best Actor awards from many film critics associations.

In celebration of Gyllenhaal's newest film, Road House, available March 21 on Prime Video, L'OFFICIEL has rounded up the actor's expansive acting career with 15 of his best films. 

In 1999, Jake Gyllenhaal took the lead role of Homer Hickam in the film October Sky, a compelling story inspired by the real-life experiences of four young men, narrated in the memoir upon which the film is based. At the time of filming, Gyllenhaal was just 17 years old and still attending school. In a 2014 interview, Gyllenhaal revealed that he received tutoring on set to balance his education with his acting career.

The actor starred in the 2004 movie The Day After Tomorrow which follows the effects of the disruption of the North Atlantic Ocean current circulation. The film portrays the catastrophic consequences of extreme weather events leading to a new ice age, with Gyllenhaal's character, Sam, among those fighting for survival.

Directed by Ang Lee, the film Brokeback Mountain, released in 2005, starred Jake Gyllenhaal as Jack Twist, a cowboy who engages in a secret romantic relationship with another cowboy, portrayed by Heath Ledger. In addition to being a masterpiece in the LGBTQ+ category, his memorable performance was critically acclaimed and solidified his reputation as a serious actor. 

Jake Gyllenhaal starred in the 2014 psychological thriller Nightcrawler as Lou Bloom, an unemployed young man who becomes a freelance journalist who films violent crime scenes to sell to local television stations. His performance was praised by critics for his ability to completely transform his persona in order to to effectively play the character.

For Prisoners, released in 2013, Jake Gyllenhaal plays the role of detective Loki. In this gripping thriller directed by Denis Villeneuve, a frantic search for two missing children ensues, paving the way for Gyllenhaal to deliver a sensational performance as a determined and tormented investigator.

This is a cult favorite among independent cinema enthusiasts and mainstream film aficionados alike. In the 2001 film Donnie Darko, the American actor plays the lead role, portraying a teenager suffering from schizophrenia who begins to receive visions of a man with a rabbit's head that guides him towards a dark destiny. His complex performance captured the attention of viewers and brought him to the attention of the public and powerful Hollywood executives.

As journalist Robert Graysmith in the 2007 film Zodiac, Gyllenhaal spins the true story of the hunt for the Zodiac serial killer of the '60s and '70s. Gyllenhaal's performance in this film has been remembered for his convincing performance as a man solely obsessed with finding the truth and seeking justice.

End of Watch, released in 2012, follows the lives of two young police officers in Los Angeles. The film presented Gyllenhaal with a fresh acting challenge and required five months of intensive training to prepare for his role. Directed by David Ayer, the movie was well-received by critics and won multiple awards, including the Best Actor in an Action Movie award, which went to Gyllenhaal.

Enemy, released in 2013, is a psychological thriller, in which the L'OFFICIEL Hommes Italia cover star plays two seemingly distant but interconnected roles: a university professor and an actor. The film explores themes of identity, dual vision, and control, which are presented through Gyllenhaal's hypnotic, structured, and complex performance.

In the 2017 science fiction thriller Source Code, directed by Duncan Jones, Gyllenhaal plays a soldier who awakens in the body of another man and must continually relive the last eight minutes of a person's life to try to prevent a terrorist attack.

Also released in 2017, Jake Gyllenhaal stars in Stronger as Jeff Bauman—a surviving victim of the 2013 Boston Marathon who lost both legs. This touching film, inspired by an authentic story, explores Bauman's struggle to overcome the aftermath of the attack and accept his new life.

Directed by American fashion designer and director Tom Ford, Nocturnal Animals is a 2016 psychological thriller based on the novel Tony and Susan by Austin Wright. The film follows Susan Morrow, a gallery owner played by Amy Adams, who receives a manuscript from her ex-husband, Edward Sheffield, played by Jake Gyllenhaal. The film intertwines the story of the novel with Susan's real life, revealing the complex dynamics of their past and present relationships. Gyllenhaal's performance has been praised for his intensity and vulnerability as Edward, while Adams delivers a stunning performance as Susan, reflecting her internal conflict and search for meaning in life.

The film, originally adapted from a novel, features Jake Gyllenhaal as John Morris and follows an infamous pair of assassins tasked with seeking vengeance against those who stole from their boss. Both the storyline and Gyllenhaal's performance captivated audiences and earned a standing ovation at the 75th Venice International Film Festival.

In his newest film, Jake Gyllenhaal plays Elwood Dalton, a former MMA fighter who earns his living by fighting underground. Road House, directed by Doug Liman, is a remake of Rowdy Herrington's 1989 film starring Patrick Swayze. Blind beatings, complicated life stories, and a gripping mystery create a balanced, complex story in the 2024 interpretation.