Jake Gyllenhaal is probably best known for his film Tom Holland in the Marvel franchise and for his terrifying portrayal in Nightcrawler. Gyllenhaal has a good balance of mainstream roles and Indie projects that makes him an interesting and well-rounded actor.
Gyllenhaal has portrayed several characters throughout the years with different personalities with great success in almost every genre of film from comedy to action-adventure and drama, but there are some roles that fans might have forgotten about.
Bubble Boy (2001) - 5.6
Jake Gyllenhaal stars in this quirky coming-of-age movie as a young adult who has been told that he was born without a functioning immune system, so he has lived his whole life in a bubble to avoid becoming sick from any outside germs. He falls in love with his neighbor and decides to create a portable bubble so he can travel across the country to stop her wedding and profess his life to her. The film came out the same year as Donnie Darko and understandably isn't the role he's known for in his career.
Prince of Persia: The Sands of Time (2010) - 6.6
Although Jake Gyllenhaal has recently starred in Spider-Man: Far From Home in the MCU he isn't well-known for his action-adventure or superhero movies, which is why Prince of Persia is one of his roles that doesn't immediately come to mind.
The film didn't perform well overall and there were issues of controversial whitewashing within the cast of characters that most don't this Jake Gyllenhaal role.
Wildlife (2018) - 6.8
This relatively unknown Indie film follows a couple and their teenage son trying to survive and keep their relationship amongst multiple hardships. Jake Gyllenhaal's father character is fired from his job as a golf pro and decides to do something more meaningful with his life in his next job. Gyllenhaal becomes a firefighter and is constantly away from home fighting wildfires. His son and wife (Carey Mulligan) have troubles at home as they try to adjust to life without him.
Enemy (2013) - 6.9
This confusing and intriguing film from Denis Villeneuve follows a history professor (Gyllenhaal) who lives a quiet life until a friend tells him about an actor (also Gyllenhaal) with which he shares a striking resemblance. The professor starts to stalk the actor, becoming obsessed with how identical they seem, and the two finally meet face to face and their lives become intertwined after the meeting.
The Sisters Brothers (2018) - 7.0
This Western film is set in the 1850s and follows two brothers (John C. Reilly and Joaquin Phoneix) who are well-known gunfighters and hired as hitmen to kill a man. Jake Gyllenhaal stars alongside the two as a private detective who has been hired to hunt down the same man as the brothers. The film has great reviews, even though it's not one of his most memorable roles, and is definitely worth a watch for any Jake Gyllenhaal fan.
Demolition (2015) - 7.0
Jake Gyllenhaal stars in this comedic drama as a man who is trying to cope with the recent death of his wife in a fatal car crash. Gyllenhaal's character is concerned that he isn't as sad or emotional as he should be after his wife's death and finds a confidant in a customer service representative. Gyllenhaal's performance ranges from unemotional to erratic as a grieving husband and the Indie film has pretty good reviews.
Brothers (2009) - 7.1
Jake Gyllenhaal and Tobey Maguire star in this psychological drama with a strong war presence at the center of the film. Maguire portrays a Marine who is deployed for combat and captured as a prisoner of war leaving behind his wife (Natalie Portman) and children. Gyllenhaal's character portrays his troubled brother who tries to get back in the family's good graces by helping Portman around the house and with the kids, but the two become too close and Maguire is a changed man when he returns home.
Everest (2015) - 7.1
Most Jake Gyllenhaal fans The Day After Tomorrow when his character has to fight for his life against a sudden storm caused by global warming, but many probably forget his role in Everest based on real-life events. Gyllenhaal stars alongside Josh Brolin in the film that follows their final ascent to the top of Mount Everest. An unexpected storm hits and the group has to decide whether to push on or begin their descent to safety.
Okja (2017) - 7.3
Okja is a unique film from director Bong Joon-ho about corporate greed as a food corporation decides to breed super pigs by having farmers raise them and have them ultimately killed for food. Mija takes care of one of the super pigs, Okja, and the two are best friends who are pulled apart when the company comes to take its property back.
Jake Gyllenhaal has a side role in this film as an over-the-top tv show host who interacts with animals. He completely changes his voice, grows a mustache, and wears an interesting ensemble for the role that makes him almost unrecognizable.
October Sky (1999) - 7.8
Jake Gyllenhaal stars as the idealistic Homer who becomes interested in rocket science and begins to build rockets with his friends and the help of his teacher (Laura Dern) even though his coal miner father doesn't the scientific path. Although this is a memorable role, it's an earlier role that happened around the same time as Donnie Darko, which overshadowed this role.
