For over 20 years Jake Gyllenhaal has built an impressive filmography while quietly storming the box office. In this weekend's Nightcrawler, Gyllenhaal is at his best playing an elusive freelance journalist in a seedy, dark Los Angeles. Critics are raving the film's raw energy and Gyllenhaal's stark performance. Since his early days as a child actor to his recent tenure as a critical and commercial favorite, Gyllenhaal has collected a nice assortment of awards and nominations, including an Academy Award nod for his work in Brokeback Mountain. Gyllenhaal comes from a Hollywood family rich in projects on both the big and small screen. In celebration of his newest endeavor and the Oscar buzz he's generating, here's a look at his best work:

10. OCTOBER SKY (1999)

Directed by Joe Johnston

Starring Jake Gyllenhaal, Chris Cooper, Laura Dern

Set in West Virginia, October Sky is a feel-good coming-of-age tale following Homer, a teenager (Gyllenhaal) growing up in a coal mining town in the late 1950s. While most boys grow up to follow in their fathers' footsteps and enter the cola mining workforce, Homer is inspired by the Sputnik to build his own, homemade rockets. The story is as sappy as an inspiring drama can be, but the Hollywood classiness in the way the story is delivered sets it apart from its made-for-TV counterparts.

9. PROOF (2005)

Directed by John Madden

Starring Gwyneth Paltrow, Anthony Hopkins, Jake Gyllenhaal

Based on the play of the same name by David Auburn, Proof is a heartbreaking drama. Paltrow's Catherine is the daughter of a mathematician (Hopkins) who has recently passed away. With the help of one of his former students (Gyllenhaal), she begins to unravel who her father really was before his death. Riddled with painfully honest performances by the entire cast, Proof is the rare small scale drama that translates amazingly from stage to screen. Each word of the script is masterfully portrayed. The film is one of those underdogs worth catching.

8. END OF WATCH (2012)

Directed by David Ayer

Starring Jake Gyllenhaal, Michael Pena, Anna Kendrick

Gyllenhaal and Pena star as young LA cops who uncover a secret so perplexing they end up on the run from one of the world's most powerful drug cartels. The film is gritty and intense, taking the audience on a front seat ride through some of the greatest action sequences in recent cinema. Director David Ayer works wonders with the relatively honest portrayal of LA's drug society and that of the cops. Kendrick shows up in a brief, but great, supporting role. It's Gyllenhaal and Pena's chemistry, though, that brings the entire film home.

7. THE GOOD GIRL (2002)

Directed by Miguel Arteta

Starring Jennifer Aniston, Jake Gyllenhaal, John C. Reilly

A darling of the festival circuit, The Good Girl tapped into a different side of "Friends" star Aniston and gave Gyllenhaal a more mainstream notoriety, despite the film being a small, indie project. Aniston starred as a woman reinventing herself by having a fling with a young coworker (Gyllenhaal). The movie was a hit at Sundance and gave rise to the fad of big-budget celebrities tackling smaller scale films with great results. There's also a great cameo by a then-not-so-known Zooey Deschanel.

6. BROTHERS (2009)

Directed by Jim Sheridan

Starring Tobey Maguire, Jake Gyllenhaal, Natalie Portman

This, like Proof, is another great film that seemed to slip through the cracks a bit. 2009 was a great year for movies, so perhaps that's why this particular film was mostly skipped over come award season. Maguire stars as Sam Cahill, a Marine heading off to a tour in Afghanistan. Before he leaves, he picks up his brother Tommy (Gyllenhaal) from prison and lets him stay with his wife Grace (Portman) and their two daughters. After Sam's aircraft is shot down, and Sam is presumed dead, Tommy vows to help Grace in taking Sam's place. The two become emotionally close before Sam reappears. The ensuing drama is dark, intense, and offers some of the best performances by all three cast members. It's a tour de force film not to be missed.

5. ZODIAC (2007)

Directed by David Fincher

Starring Jake Gyllenhaal, Mark Ruffalo, Robert Downey Jr.

Before Fincher became the Academy Award favorite that he is now, thanks to The Social Network, his dark, static thrillers were understated and violent in the best way. His style is still apparent, but it's his no-hold-barred approach to stories like Zodiac that really seemed to set him apart. Gyllenhaal plays one of four men bent on finding the Zodiac Killer, an infamous mass murderer wreaking havoc around San Francisco. The true story, based on the book by Robert Graysmith (who Gyllenhaal plays), is all things edge-of-your-seat and classic Fincherian fun. If you like Fincher's earlier works Se7en and Fight Club, Zodiac is a must see.

4. JARHEAD (2005)

Directed by Sam Mendes

Starring Jake Gyllenhaal, Jamie Foxx, Peter Sarsgaard

The mid-aughts were a great time for Gyllenhaal's career as best seen in this military movie by acclaimed director Mendes. Gyllenhaal plays the somewhat naïve rookie Marine as he navigates from boot camp into active duty in the midst of war. The film had its own set of hardships as it was released in the midst of the real war in Iraq, but any misconceived notions put in place were actually just food for thought. Gyllenhaal knocked his portrayal of the emotionally disturbed and heavily influenced Swoff out of the park. Equally, Jamie Foxx capitalized on an already impressive few years by bringing a certain humanity to role of the masterfully tough drill sergeant. The film also features some incredible cinematography by the master Roger Deakins. When ranking war films, this one will find its place among the best.


Directed by Ang Lee

Starring Heath Ledger, Jake Gyllenhaal, Michelle Williams

The subject matter of Brokeback Mountain has been the topic of plenty of controversy, but despite that, the film itself is actually a pretty incredible tale of the loss and loneliness that life puts in our paths. Ledger and Gyllenhaal each received Oscar nominations for their work as a ranch-hand and rodeo cowboy who fall in love after meeting while driving cattle through Wyoming. Director Lee tackled the story by providing the perfect mixture of sweeping visuals and beautiful scoring that translates into a great tale of the American spirit. The film often gets pushed to the side, but is deserving of a watch, if not for the performances of Ledger and Gyllenhaal, then for the masterful filmmaking on display.

2. DONNIE DARKO (2001)

Directed by Richard Kelly

Starring Jake Gyllenhaal, Jena Malone, Patrick Swayze

Perhaps Gyllenhaal's truest breakthrough performance was as the deeply disturbed Donnie Darko in this twisting and turning cult favorite. The story of the film's journey to the big screen is almost as interesting as the film itself. Darko is a teenager who goes back and forth between moments of sincerity and disillusion. Gyllenhaal is the perfect mix of charm and rebellion. Each layer of the story is so carefully placed that it practically begs for repeat viewings. There are some great supporting turns that pop up by the likes of Drew Barrymore, Noah Wyle, Beth Grant, Maggie Gyllenhaal (Jake's sister), and an unknown Seth Rogen. In the years since Donnie Darko's release the film has grown into a highly-praised and widely-loved must-see cult classic. The sequel that followed was not so much.

1. PRISONERS (2013)

Directed by Denis Villeneuve

Starring Jake Gyllenhaal, Hugh Jackman, Paul Dano

Featuring the incredibly precise cinematography of Roger Deakins, Prisoners is a edge-of-your-seat thrill ride like none other. Gyllenhaal stars as a detective bent on uncovering the truth behind two missing girls. Jackman plays the father of one of these girls who will stop at nothing to find his daughter, even if that means getting arrested himself. Dano enters the mix as a strange man who is both creepy and innocently peculiar. The twists and turns on display here are top notch. Director Villeneuve masterfully weaves a tale of suspense so rich in quality that it's impossible to watch this and not be moved in some way. It's one of Gyllenhaal's strongest performances. He doesn't let down in any sense of the word. There are clear character choices being made that take this above and beyond your average action thriller.

© 2018 by Scottie Knollin.