This list has been updated by Charlene Badasie.
Jake Gyllenhaal has built one of the most storied careers in Hollywood, effortlessly moving between massive blockbusters, intimate character studies, and daring independent films. From his early breakout performances as a sensitive dreamer to his later roles as morally ambiguous and psychologically complex figures, Gyllenhaal has demonstrated a rare willingness to take risks.
Many of Gyllenhaal's films are currently available to watch on major streaming platforms like HBO Max, Prime Video, Netflix. With that in mind, we're ranking some of his top movies from worst to best, celebrating not only his finest performances but also the movies that best capture his remarkable versatility and lasting impact on modern cinema.
October Sky (1999)
Based on a true story, October Sky follows Homer Hickam (Gyllenhaal), a small-town boy inspired by the launch of Sputnik to pursue his dream of building rockets. Against his father's wishes, Homer and his friends work tirelessly to prove their scientific abilities. This is one of Gyllenhaal's most sincere and uplifting performances, anchored by earnestness rather than intensity.
While it lacks a lot of the complexity of his later projects, it brilliantly showcases the emotional clarity and screen presence Gyllenhaal can bring to any role. The movie also earns its place on the list for being the foundation of his career. October Sky is a must for viewers who enjoy watching inspirational, family-friendly dramas. It lands in last place because it is gentler and less psychologically challenging than the films that follow.
Donnie Darko (2001)
Donnie Darko centers on a troubled teenager named Donnie (Gyllenhaal), who begins having visions of a mysterious figure in a rabbit costume predicting the end of the world. His parents eventually send him to therapy, as the lines between Donnie's reality and fantasy begin to blur. The story plays out as a haunting exploration of fate, time, and mental illness.
Gyllenhaal's performance in this film established him as a serious actor capable of playing unsettling characters. His portrayal of Donnie is vulnerable and eerie, which anchors the film's ambiguous tone. It ranks higher than October Sky for its artistic boldness and is ideal for fans of surreal, mind-bending storytelling.
End of Watch (2012)
End of Watch follows Brian Taylor (Gyllenhaal) and Mike Zavala (Michael Peña), two police officers who patrol South Central Los Angeles. The story focuses on their close brotherly bond and the dangerous nature of their job. Things take a deadly turn when the pair cross paths with a notorious Mexican drug cartel. Gyllenhaal brings warmth and realism to a role grounded in moral responsibility.
End of Watch's found-footage approach (derived from cameras worn by the actors' characters) adds urgency to the story, but it can feel stylistically limiting in some places. It ranks above Donnie Darko for its emotional accessibility and realism. The movie is perfect for viewers who enjoy intense, character-driven crime dramas.
Nightcrawler (2014)
Nightcrawler follows Louis Bloom (Gyllenhaal), a freelance cameraman who films violent crime scenes to sell to a local Los Angeles news network run by producer Nina (Rene Russo). As his ambition grows, so does his moral detachment, manipulating scenes to get better footage to feed the "if it bleeds, it leads" media culture.
Nightcrawler is one of Gyllenhaal's most disturbing and fully realized performances. His physical transformation and cold detachment make Lou Bloom unforgettable. It ranks higher than End of Watch for its psychological edge and social commentary. The movie, which is ideal for fans of dark psychological thrillers, also received an Academy Award nomination for Best Original Screenplay.
Prisoners (2013)
Prisoners follows Keller Dover (Hugh Jackman), who is devastated when his six-year-old daughter and her friend go missing. When Detective Loki (Gyllenhaal), who is assigned to the case, has to let the only suspect, Alex Jones (Paul Dano), go due to lack of evidence, Keller decides to take matters into his own hands by kidnapping and torturing him.
The film is essentially a chilling exploration of the limits of justice, grief, and morality. And Gyllenhaal's restrained, focused performance contrasts nicely with Jackman's emotional volatility. It only ranks above Nightcrawler for its thematic complexity. The movie is ideal for anyone who appreciates intense dramas with a heavy moral message, like The Guilty (2021), which also stars Gyllenhaal.
Southpaw (2015)
Southpaw follows champion boxer Billy "The Great" Hope (Gyllenhaal), whose life falls apart after personal tragedy. He eventually finds help in former fighter Tick Willis (Forest Whitaker), who trains the city's toughest amateur boxers. Together, they work to rebuild Billy's career and relationship with his wife, Maureen (Rachel McAdams), and daughter, Leila (Oona Laurence).
Gyllenhaal is brilliant in Southpaw, with his physical transformation and emotional vulnerability elevating what would ordinarily have been a familiar sports story. It lands in the middle of the list for its emotional accessibility. It's a must for anyone who enjoys inspirational sports dramas like Ali (2001), starring Will Smith.
Stronger (2017)
Based on a true story, Stronger tells the story of Jeff Bauman (played by Gyllenhaal), who lost both legs in the 2013 Boston Marathon bombing. The story chronicles his physical recovery, psychological struggles, unwanted attention from the media, and his sometimes strained relationship with his girlfriend, Erin (Tatiana Maslany).
Although Stronger failed to impress at the box office, the movie sees Gyllenhaal deliver one of his most emotionally honest performances. The film avoids sentimentality while embracing vulnerability and ranks higher than Southpaw for its realism. It is an ideal choice for viewers who enjoy biopics, even if the subject matter is more uncomfortable than glamorous.
Jarhead (2005)
Jarhead examines the real-life experience of U.S. Marine Anthony Swofford (played by Gyllenhaal) before and during the Gulf War. The story chronicles his boot camp training, which includes a sniper course led by Sergeant Sykes (Jamie Foxx). When the United States becomes directly involved in the war, Swofford is shipped out with his spotter, Alan Troy (Peter Sarsgaard).
While it is a war movie, Jarhead is more about psychological endurance than combat and explosions, which reflects the monotony and disillusionment of military life. It is also one of Gyllenhaal's most understated performances as his internalized portrayal captures confusion and frustration. It lands in third place for its thematic originality and is ideal for viewers who appreciate anti-war narratives.
Zodiac (2007)
Zodiac chronicles the real-life hunt for the Zodiac Killer, who terrorized the San Francisco Bay Area during the late 1960s and early 1970s. The film follows journalists and investigators Robert Graysmith (played by Gyllenhaal), Dave Toschi (Mark Ruffalo), Paul Avery (Robert Downey Jr.), and Bill Armstrong (Anthony Edwards), whose obsession with the killer slowly erodes their personal lives.
Meanwhile, the Zodiac Killer continues to claim more victims and taunts the authorities with cryptic messages and phone calls. The film is an intellectually gripping and methodical reconstruction of arguably the most famous unsolved case in the United States. The movie is ideal for fans of procedural thrillers and earns second place for its narrative precision and lasting intrigue.
Brokeback Mountain (2005)
Set in the early 1960s, Brokeback Mountain tells the story of ranch hand Ennis Del Mar (Heath Ledger) and rodeo cowboy Jack Twist (Gyllenhaal), who form a secret romantic relationship that spans decades. Due to societal pressure and personal repression, which forces them into heterosexual marriages, the movie plays out as a sweeping, tragic love story.
The Academy Award-winning Brokeback Mountain is based on Annie Proulx's 1997 short story of the same name. The movie earns the number one spot for offering up Gyllenhaal's most emotionally resonant and culturally significant performance. His portrayal of Jack's longing and fear is the best example of his dramatic power. The movie is a must for fans of emotionally rich romantic dramas.
