Jake Gyllenhaal is currently one of Hollywood’s most popular actors, perhaps one of the most impressive actors of his generation. He is one of the few movie stars who can effortlessly switch between smaller indie films and big-budget popcorn movies, while always delivering interesting performances.
While Gyllenhaal is certainly a high-profile actor, his penchant for taking on challenging parts means that some of his roles can get overlooked. From early on in his career to more recent films, some of the work on his resume remains undiscovered by even his biggest fans.
City Slickers
Some fans might be surprised to know that Gyllenhaal has been in the movie business since he was just a small child. Though he found his success in his early adult years, he did make a solid career for himself even when he was little more than a toddler. His appearance in this comedy classic, for instance.
City Slickers follows a group of big city yuppies who deal with their midlife crisis by participating in a cattle drive. Gyllenhaal has a small role as the son of Billy Crystal’s character. It’s hard to imagine that small kid would grow to be a massive movie star.
The Sisters Brothers
The Sisters Brothers only came out last year. Despite an impressive cast, it was sadly one of the most overlooked films of 2018. This modern Western might not have been the action-packed adventure audiences were hoping for, but it was a beautiful, funny and emotional tale.
The film follows the titular brothers (played by John C. Reilly and Joaquin Phoenix), who are guns for hire on the trail of a mysterious businessman. Gyllenhaal plays an associate of the brothers who forms an unlikely friendship with their target.
Rendition
In the years following the tragedy of 9/11, there were a slew of high profile “war on terror”-themed movies that tackled both the modern threat and the complications of fighting against it. Gyllenhaal starred in one of these films, Rendition, which involved the highly controversial abductions and intense interrogation tactics of the CIA.
Gyllenhaal plays a CIA analyst assigned to oversee one such case, the interrogation of a man he believes to be innocent. Despite co-starring Oscar winners like Reese Witherspoon, Alan Arkin, and Meryl Streep, the film was a critical and commercial disappointment.
The Day After Tomorrow
Roland Emmerich is the man responsible for such end-of-the-world disaster blockbusters as Independence Day, 2012 and this 2002 hit. The movie takes the dangers of climate change and dials it up to eleven. As tornadoes and tsunamis begin to destroy the world, those who remain fight for survival in a new ice age.
The film stars Dennis Quaid as a climatologist while Gyllenhaal plays his son, who leads a group of survivors in New York City. Not exactly a role in which he needed to stretch his acting muscles, but it marked Gyllenhaal’s first foray into blockbuster film-making.
Everest
Though Gyllenhaal is often the leading man of his films, he is not above playing a supporting role every now and then. In Everest, Gyllenhaal was just one part of an all-star cast which included Jason Clarke, Josh Brolin and Keira Knightley.
The film tells the true story of a 1996 Everest expedition, which saw a group of climbers trapped by a blizzard on the top of the mountain. Gyllenhaal plays real-life climber Scott Fischer, who was part of the doomed climb. It’s interesting seeing a star of Gyllenhaal’s calibre in a smaller role, part of a larger ensemble in this intense survival story.
Accidental Love
Gyllenhaal has largely avoided the traditional romantic comedies. When he does dabble in those kinds of films, it’s usually a unique take on the genre. In Accidental Love, Jessica Biel plays a woman who is shot in the head with a nail gun, an incident that has unusual results. Her condition is then exploited by an unscrupulous Congressman, played by Gyllenhaal.
Despite being directed by acclaimed filmmaker David O. Russell, the movie went through massive production issues, being re-edited to the point that Russell declined his credit. The result was a mess of a film which was unceremoniously dumped on VOD.
Brothers
Legend has it that Gyllenhaal was once considered as a replacement for Tobey Maguire (who had suffered a back injury) as the star of Spider-Man 2. Though that didn’t come to pass, the two would eventually share the screen in this intense drama.
In this remake of a Danish film, Maguire plays a Marine who goes missing in action. Gyllenhaal plays his wayward brother who steps in to take care of Maguire’s family. Things get tense when Maguire returns home, severely damaged by his experience. Along with Natalie Portman and Maguire, Gyllenhaal helps make this a compelling acting showcase.
Enemy
Denis Villeneuve has become one of the most respected directors currently in the business. Having made films like Arrival, Sicario and Blade Runner 2049, Villeneuve has shown to be a master of atmospheric thrillers. However, this lesser-known mystery is mostly overlooked in his filmography.
Villeneuve reunited with Gyllenhaal, his star in Prisoners, in this strange story of a man who discovers he has a doppelgänger. Filled with some creepy visuals and a much-discussed ending, it is the kind of movie that doesn’t give its audiences any easy answers.
Zodiac
Zodiac had visionary director David Fincher at the helm. It had a cast including Gyllenhaal and a pre-Avengers Robert Downey Jr. and Mark Ruffalo. It even had a subject as compelling as the infamous Zodiac killings. How is it not more widely known?
While not the bloody thriller you might imagine from the director of Se7en, the film is a methodical examination of the decades-long investigation of the murders. In this brilliant crime saga, Gyllenhaal gives a surprisingly funny and obsessive performance as one of the people searching for the true Zodiac.
Bubble Boy
Despite his penchant for intense dramas, Gyllenhaal has shown he has a real talent for comedy too (in those rare times he does embrace his funny side). However, in this very early role of his, Gyllenhaal decided to go full-blown silly in a way we have not seen from him since.
In Bubble Boy, Gyllenhaal stars as a boy without an immune system, forced to live in a protective bubble. When he learns the love of his life is getting married, he sets out on a cross-country quest to stop the wedding. Though it failed to make much of an impact when it was released, the film has gained a small cult following – although it might be a film Gyllenhaal wishes would remain forgotten.