20. City Slickers (1991)
Like many comedy films of its era, “City Slickers” hasn’t aged particularly well, but it hasn’t lost any of its charm or some of its humor. The young Jake Gyllenhaal’s (who looks exactly the same but obviously way younger) first film was in a very brief role as the son of Billy Crystal’s lead character who goes on a two-week journey through the Wild West with his city slicker pals, all facing midlife crises’ of some kind.
19. Moonlight Mile (2002)
Inspired by writer/director Brad Silberling’s own personal experience after his girlfriend Rebecca Schaeffer, an actress on her way to big things, was murdered by an obsessed fan in 1989, “Moonlight Mile” follows Jake Gyllenhaal dealing with a similar experience after his fiancé is murdered in a restaurant. He’s taken in by his fiancé’s parents, played by Dustin Hoffman and Susan Sarandon, who are also struggling with the loss.
A meditation on death and mourning, “Moonlight Mile” gives a portrait of people in grief who find a way to carry on by leaning on each other. The performances are excellent across the board, as is Silberling’s script and direction. While never becoming a masterpiece, Silberling adds in some fresh touches that overcome cliché, especially when dealing with the guilt of moving on and falling for someone new.
18. Proof (2005)
Following similar films about brilliant mathematicians with mental problems, “Proof” stands out from the pack for its depth. Rather than overplay the math or character problems, the film is much more subdued, which makes for a unique viewing experience.
Based on the Pulitzer Prize-winning play of the same name about the daughter of a brilliant mathematician, who has mixed feelings about proving that her deceased father’s late career writings were actually written by herself. Acclaimed for its accurate portrayal of mathematics, mathematicians and their lives, the cast of Gwyneth Paltrow, Hope Davis, Anthony Hopkins and Gyllenhaal sell every scene to perfection.
17. Everest (2015)
Aside from its star-studded ensemble that includes Jason Clarke, Josh Brolin, Robin Wright, Keira Knightley, Emily Watson, John Hawkes, Michael Kelly and Sam Worthington, alongside some eye-popping and breathtaking visuals, “Everest” never really becomes anything special or memorable. It’s at its best when it shows the mountains and storms.
Based on Beck Weathers’ memoir about his experience and survival during the 1996 Mount Everest disaster, Gyllenhaal plays one expedition group leader who tries to lead his group to safety. The group of actors makes the most with what they’re given, even if it feels more like an extremely beautiful and polished documentary.
16. The Good Girl (2002)
Jennifer Aniston proved her diversity and acting chops with a more dramatic role in this indie dramedy. She plays a depressed “good girl” who’s stuck in a small town, a dead end job, and a loveless marriage with John C. Reilly (who spends all his free time smoking weed with his pal Tim Blake Nelson), until, that is, Jake Gyllenhaal comes into the picture.
They both share an instant chemistry and bring some happiness into their otherwise mundane and depressing lives. With a smart script, strong direction, and great performances, “The Good Girl” belongs to Aniston, who makes Rachel from “Friends” a thing of the past. An excellent film that never shies away from the darkness or takes the easy way out.
15. Lovely & Amazing (2001)
Nicole Holofcener’s dramedy is a quiet and subtle look at womanhood through four women: a matriarch, her two adult daughters, and her adopted pre-teen African-American daughter. More concerned with its characters than its plot, “Lovely & Amazing” is an honest look at the everyday lives of these real women that is way more entertaining than it sounds.
It’s a slice-of-life story that subtly shows how certain things are passed down the line. Like a cool breeze, it flows through its characters and strong performances that sees Gyllenhaal playing a teenager who’s romantically involved with Catherine Keener’s much older woman.
14. Jarhead (2005)
“Jarhead” is a film that conjures up mixed feelings. On one hand, it’s a unique war picture with some amazing visuals and performances to boot. On the other hand, it’s repetitious and leaves you empty and wanting more by the time the credits roll.
Based on Anthony Swofford’s memoir that details his vigorous training, initiation, and selection into sniper training, Swofford and his platoon eventually arrive in the desert during the Gulf War, only to find boredom. All the terror and violence they were taught to expect during training is nowhere to be found except for high temperatures, pointless drills, an ocean of sand, and a lot of waiting.
13. Brothers (2009)
Jim Sheridan’s remake of Susanne Bier’s Danish film “Brødre” is said to be safer and less powerful than the original, although a still good film by those who’ve seen both versions. But for those of us who still plan to see Ms. Bier’s version, “Brothers” holds its own as an underrated yet slightly flawed film.
It stars a never-better Tobey Maguire as a U.S. Marine who’s taken hostage by Taliban fighters in Afghanistan, and the void he leaves back home with his wife, played by Natalie Portman, when he’s presumed dead. Thus comes in Gyllenhaal as the screw-up brother who tries to take care of his brother’s family during their time of mourning, which evolves into much temptation and soul-searching.
12. Nocturnal Animals (2016)
Based on Austin Wright’s 1993 novel, “Nocturnal Animals” saw Gyllenhaal play dual roles in Tom Ford’s second directorial feature. First playing the ex-husband to Amy Adams’ character, who sends her his latest novel that appears to be inspired by their relationship, and then secondly as a character in the same novel she’s reading.
It’s a thought-provoking film that, although set in present times, has a ‘90s feel to it, much in line with the psychological thrillers of the time. With themes of masculinity and symbolism, Gyllenhaal does most of the lifting and has the most to do with a cast that also includes a memorable Michael Shannon and Aaron Taylor-Johnson.
11. October Sky (1999)
The first film that showed exactly what Jake Gyllenhaal was capable of and what a talent he is. “October Sky” is the actor’s breakout film. A biographical drama based on Homer H. Hickam Jr., a coal miner’s son who goes against his father’s wishes to become a NASA engineer after seeing the launch of Sputnik 1.
It’s the exact type of feel-good family drama about beating the odds and following your dreams. It falls into similar inspirational storytelling clichés we’ve seen countless times before which makes an all-too-safe biopic. What makes it memorable, however, is the fine acting by Gyllenhaal as Homer Hickam and Chris Cooper as the father he constantly clashes with to follow his dreams.