Jake Gyllenhaal has become one of the biggest stars in Hollywood and one of the most reliable leading men in films. He started acting at a young age before finding success with lead performances in small but standout films. Since then, he has built an incredible career filled with big blockbusters, intimate dramas, and unforgettable roles.
Gyllenhaal's filmography is filled with films that will go down as amazing achievements. Of course, there are also those more forgettable films or the ones fans wish they could forget.
Best: Zodiac (2007) - 7.7
David Fincher took on one of the most infamous serial killer cases in history with the crime masterpiece Zodiac. The film chronicles the various figures involved with the decades-long investigation of the Zodiac Killer, with Gyllenhaal playing Robert Graysmith, one of the case's most dedicated investigators.
With years of evidence and speculation, the film tells a vast and fascinating story of a still-unsolved case. There is horror, suspense, and some well-placed humor courtesy of Robert Downey Jr. in a fine supporting role.
Worst: A Dangerous Woman (1993) - 5.8
Though fairly underseen, A Dangerous Woman was a significant film for the entire Gyllenhaal family. It was written by Jake's mother, directed by his father, and served as early roles for himself and his sister Maggie Gyllenhaal.
The film stars Debra Winger as a naïve woman who struggles to be taken seriously by those around her. The family affair, unfortunately, resulted in a fairly forgettable film that was criticized for its melodramatic approach.
Best: October Sky (1999) - 7.8
Gyllenhaal secured one of his first leading man performances in the charming real-life story, October Sky. Gyllenhaal plays a young man living in a small coal-mining town who is inspired by the Sputnik satellite launch to build a rocket of his own.
At a young age, Gyllenhaal carries the film exceedingly well. He makes for a sympathetic and inspiring hero, while also holding his own in his scenes opposite Chris Cooper as his stern but caring father. It's a moving and entertaining adventure.
Worst: Josh And S.A.M. (1993) 5.7
The road trip comedy Josh and S.A.M. was another early role for Gyllenhaal when he was still working as a child actor. The film follows two brothers who go on a wild cross-country adventure after stealing a car and running from the law.
The storyline of young kids running wild didn't seem to interest many viewers. The movie has become another forgotten film of the 90s, with any real interest in it coming from Gyllenhaal's small supporting role.
Best: Nightcrawler (2014) - 7.9
Though he is often seen in heroic roles, Gyllenhaal made for a chilling deranged protagonist in the thriller Nightcrawler. He plays an ambitious and dangerous man who attempts to find success in the world of freelance news cameramen. He soon proves he's willing to push the limits to be the best in the business.
It is a dark and compelling journey into a seedy world. Gyllenhaal gives one of his best performances to date, as someone who almost seems charming at times, but is really a terrifying individual who pursues success at any cost.
Worst: Velvet Buzzsaw (2019) - 5.7
Gyllenhaal teamed up with Nightcrawler director Tony Gilroy with much less successful results. Velvet Buzzsaw is a strange horror-comedy set in the world of modern art. The film follows a group of people in the art world who become the target of a strange and possibly supernatural killer.
Despite the winning cast, which also includes Rene Russo and Toni Collette, Velvet Buzzsaw received a mixed response from audiences. Some found it to be a clever satire of the art world, while others found it failed at both horror and comedy.
Best: Donnie Darko (2001) - 8.0
Gyllenhaal found his true breakout performance in the indie sci-fi mystery Donnie Darko. He plays the titular character, a young man who, after narrowly avoiding death in a freak accident, starts having visions of a creature who tells him to carry out destructive acts.
Though the movie might be a bit to take in with a single viewing, the film became a cult hit. Its surreal storytelling keeps the audience guessing as to where it is all leading. Gyllenhaal makes for an excellent lead in the difficult role that is pivotal to the film's success.
Worst: Bubble Boy (2001) - 5.6
While Gyllenhaal has shown he has a talent for comedy, his early starring role in Bubble Boy is perhaps not the best example. He plays a young man who suffers from a weak immune system and must live in a plastic bubble. However, he doesn’t let that stop him from heading out to stop the wedding of the girl he loves.
The movie's zany sense of humor didn't work for most viewers, who found it to be an unfunny road trip comedy. Gyllenhaal gives it his best, but he might not have been the right man for the role.
Best: Prisoners (2013) - 8.1
Acclaimed filmmaker Denis Villeneuve made his Hollywood debut in this intense thriller. Prisoners stars Hugh Jackman as a father who takes the law into his own hands when his young daughter goes missing. Gyllenhaal co-stars as the dedicated detective on the case.
Villeneuve creates a dark and haunting crime story. Jackman gives one of his best performances as the tortured family pushed to extremes, while Gyllenhaal is excellent as the cop who is pushed to the limits, as well.
Worst: Accidental Love (2015) 4.1
The idea of Gyllenhaal teaming up with David O. Russell for a satire sounds like a recipe for a great film. Accidental Love shows just how wrong even the most promising movie can go. Jessica Biel stars as a woman who is shot in the head with a nail gun and seeks the help of a young senator to help her condition.
With all the various behind the scenes drama that the film experienced, it's impossible to say what the original idea was for this story. However, many felt that the movie they got was an unfocused and unfunny mess.