Jake Gyllenhaal has always been a versatile actor, and throughout his career, he has chosen some very interesting roles. While most people got to know him in Donnie Darko, he went on to work in various dramas, action movies, fantasy releases, sci-fi efforts, and even a Marvel superhero movie.
What makes Gyllenhaal so fascinating is that he can take a character that people mostly hate, and give him some traits that make him likable, almost begrudgingly. He can then move into a role where he is the good guy, but give him a bit more that makes people wonder if they should be cheering him on, making all his characters more well-rounded than they are even written.
Mysterio In Spider-Man: Far From Home (2019)
In 2019, Jake Gyllenhaal took a role in a Marvel Cinematic Universe movie where he played Quentin Beck, the villain known as Mysterio. While it might seem strange, Mysterio was a likable character in Spider-Man: Far From Home until his evil turn late in the movie.
Before he revealed his true motives, Mysterio was one of the nicest people in the movie. He even sat down and helped Peter Parker work out his issues with MJ and really didn't want to hurt Peter at all. However, in the end, he ruined Spider-Man's life, ending any goodwill he had built up.
Sam Hall In The Day After Tomorrow (2004)
Roland Emmerich has based his career on making almost nothing by never-ending disaster movies. In 2004, he used global warming to destroy the planet in The Day After Tomorrow. In the movie, Dennis Quaid plays a paleoclimatologist named Jack during the coming of the next Ice Age.
The drama here isn't the disaster as much as it is about Jack finding and rescuing his son Sam and his friends, who are trapped in New York City. Gyllenhaal plays Sam, and it is his ability to remain likable and vulnerable that allows the movie to maintain its heart.
Anthony Swofford In Jarhead (2005)
In 2005, Jake Gyllenhaal starred in the Gulf War movie Jarhead. The fact it is a war movie makes it a little hard to hit all the notes needed to make a character innately likable. It also doesn't help that the movie is one of the most accurate war movies, and what happens is horrifying.
Gyllenhaal plays Anthony Swofford, on whose book the movie is based. He plays the Marine not as the rough and rigged soldier that many movies display them as, but as a human and one who is idealistic and loyal to his fellow soldiers.
Donnie Darko In Donnie Darko (2001)
Donnie Darko was the movie that helped introduce Jake Gyllenhaal to the world, even though he had roles as a young actor as well. In this movie, a piece of a space station crashed into Donnie's house and he would have died if he had been at home.
However, what happens next is a twisty sci-fi tale where Donnie realizes that he has little control over his actual fate. While the hero here, Donnie is almost sleepwalking through life, not knowing what is real and what is in his mind. He is relatable but not as likable as other Gyllenhaal lead roles.
Colter Stevens In Source Code (2011)
After making his name on the brilliant low-budget science fiction movie Source Code. In this movie, Jake Gyllenhaal played another soldier, this one trying to stop a train bombing.
The twist here is that when he failed, the train exploded and he found himself alive again on the train, looking for more clues. As someone who died constantly throughout the movie, it was important to like the character and Gyllenhaal made it easy to get behind him and want him to finally make it out alive.
Daniel Robbins In City Slickers (1991)
It is impossible to look at Jake Gyllenhaal's most likable roles without looking at the movie that started his career. In 1991, at the age of 11, Gyllenhaal played Billy Crystal's son in City Slickers.
The movie saw three middle-aged men go on a cattle drive, thinking it would be an adventure. The role is small, but Gyllenhaal was a cute kid and proved he had a career ahead of him, one that he excelled at.
Jack Twist In Brokeback Mountain (2005)
Jake Gyllenhaal took on one of the lead roles in Oscar-winning director Ang Lee's Brokeback Mountain. In this movie, Jake and Heath Ledger played two cowboys after a trip through the mountains where their love for each other tore them apart.
Gyllenhaal and Ledger turn in award-caliber performances that show their love, despite everything in the world working against them. While it has become somewhat of a punchline for some people, it is a movie about true love and Gyllenhaal makes the viewer care about him to the end.
Jeff Bauman In Stronger (2017)
Released in 2017, Jake Gyllenhaal took on the lead role in a true-life biopic called Stronger. The movie tells the story of Jeff Bauman, a Boston native who lost his legs in the Boston Marathon bombings and has to deal with his new life.
Gyllenhaal is able to take the character and put him through all the phases of recovery. There are moments where he is very unlikeable, but based on his situation, that is normal, and by the time he finally comes to with his new life, it is a triumphant moment.
Daston In Prince Of Persia: The Sands Of Time (2010)
Jake Gyllenhaal's video game movie. Based on the popular game franchise, Jake played Prince Daston, a former street urchin taken in by the kindly king. However, when someone kills the king and frames Daston, he has to clear his name and avenge his adoptive father's death.
Gyllenhaal is immensely likable in this movie. When he meets his love interest and she berates him, it is easy to feel for the character. He has the viewers on his side every step of the way, even as Daston learns his villain is using magic to attempt to destroy the world.
Homer Hickam In October Sky (1999)
Jake Gyllenhaal was 19 when he starred in October Sky, a movie by director Joe Johnston. The movie was a true story based on a memoir by Homer Hickam, and Gyllenhaal played Hickman in the movie.
Hickman was the son of a coal miner who saw the launch of Sputnik 1 and decided to take up rocketry before becoming a NASA engineer. As a young man living in West Virginia, with little chance of getting out, Gyllenhaal made this young man likable and viewers cheered when he finally achieved his dreams.
