1. "Moonlight Mile" (2002)
Jake plays Joe, a young man whose fiancée has recently been killed. He moves in with her parents to grieve together. The tension? The parents want him to testify against the murderer, but Joe has second thoughts. Throw in a romantic interest with a local bar owner, and you've got yourself a full plate of complicated emotions.
2. "Proof" (2005)
What happens when you mix math, mental illness, and romance? You get "Proof." Gyllenhaal plays Hal, a grad student who delves into the work of a recently deceased math genius.
Catherine, the genius's daughter, might have inherited her father's intellect as well as his mental instability. Hal believes her father's last great theorem exists, and he goes to great lengths to find it in his scribbles. Yet, the question lingers – is Catherine a genius or unstable like her father?
3. "Brothers" (2009)
If you're in for a heart-wrenching family drama, here it is. Jake stars as Tommy Cahill, whose older brother Sam is thought to have been killed in Afghanistan. Tommy steps up, helping his sister-in-law and her two daughters through the emotional aftermath.
Just when he starts to fill the gap his brother left, Sam returns, alive but traumatized. Let's just say family dinners become really awkward, really fast.
4. "Rendition" (2007)
Jake plays Douglas Freeman, a CIA analyst thrown into the deep end. An Egyptian-American is suspected of terrorism, and Douglas oversees his "extraordinary rendition"– aka, sending him abroad for interrogation and torture. As he learns more about the suspect and sees the brutal methods used, Douglas starts questioning the ethics of his own government, as one does.
5. "The Good Girl" (2002)
Jake's character, Holden, is a depressed young man who becomes romantically entangled with Jennifer Aniston's character, Justine, a married retail worker. Justine becomes increasingly discontented with her mundane life, and an affair with Holden seems like an escape route. But, as they say, the grass isn't always greener on the other side.
6. "Love & Other Drugs" (2010)
Jake plays Jamie Randall, a charming pharmaceutical rep. His path crosses with Maggie, played by Anne Hathaway, who's got early-onset Parkinson's. Instead of your standard 'boy-meets-girl,' we've got 'boy-meets-girl, they both struggle with real-world problems while dealing with the pitfalls of the healthcare system.'
7. "Bubble Boy" (2001)
In one of his earliest roles, Jake plays Jimmy, born without an immune system, living life in a plastic bubble. When the girl-next-door whom he loves is getting married, Jimmy builds a mobile bubble suit and goes out of his way to stop her wedding. The movie is a cross-country road trip with lots of quirky characters, including cult members and a biker gang.
8. "Demolition" (2015)
Gyllenhaal gives a stellar performance as Davis, an investment banker whose wife dies in a car accident. Instead of grieving conventionally, Davis becomes obsessed with taking things apart – first, a refrigerator and then, symbolically, his whole life. He befriends a customer service rep after writing a series of bizarre complaint letters about a vending machine.
9. "Source Code" (2011)
In this sci-fi thriller, Jake plays Colter Stevens, a soldier who wakes up in another man's body on a commuter train. A bomb goes off, the train explodes, and then he's back in a capsule being debriefed by military personnel. Yeah, talk about a bad day.
Turns out, he's part of a program that allows him to relive the last 8 minutes of a person's life. His mission? Find the bomber to prevent another attack.
10. "Accidental Love" (2015)
Jake takes on the role of Howard Birdwell, a small-town Congressman in this political satire. A waitress, played by Jessica Biel, gets a nail accidentally lodged in her head, leading to unpredictable behavior. She sets out to get the dysfunctional government to address her plight, and that's where Jake comes in.