His upcoming role in Duncan Jones’ second film Source Code is just around the corner and sounds similar to a few too many movies we have seen before like the recent The Adjustment Bureau. With trust in Jones, who brilliantly crafted 2009’s Moon, the movie may be a big hit for Gyllenhaal following his series of duds like Brothers, Prince of Persia and Love and Other Drugs.

Gyllenhaal broke out after his role in October Sky, landing him a role as the iconic Donnie Darko. In his early years he played the mysterious, troubled boy in transition with subtle angst that defined his generation so well. Gyllenhaal has only had one real commercial hit with the doomsday dud The Day After Tomorrow, and instead has found himself success in mid-budget films that allow him to capitalize on his ability to be the desired lead or play on his boyish masculinity like Jarhead, Brokeback Mountain and Zodiac. With only really a decade of acting under his belt, Gyllenhaal has managed to star in a handful of great films.

Donnie Darko– It is easily Gyllenhaal’s most iconic and recognizable role of his career. The cult film was initially slated for direct-to-video before being picked up at the last minute. Even so, the film was a commercial flop until a few years later when it picked up on the DVD market; especially given Gyllenhaal began breaking out with bigger, more mainstream films. Darko is a great, small science fiction film with a twist ending mainstream audiences crave. Gyllenhaal begins all his career staples here, playing the troubled boy dealing with pressures of the world.

Lovely and Amazing– It may just be a chick flick done well, but the fact that it is well done speaks a lot for this small, going-nowhere, observation film. Gyllenhaal is merely Jordan the one-hour photo store boy who finds himself mixed up in a romance with a much older woman and failed artist attempting to take care of her family. Gyllenhaal doesn’t add a lot besides his boyishly charming smile and charismatic sex appeal, but the film and story are good enough to make this a great role and opportunity to capitalize on his typecast.

Brokeback Mountain– In the doomed, tragic love affair between Ennis Del Mar and Jack Twist, Gyllenhaal is the less repressed and more hopeless romantic Jack. Gyllenhaal and Ledger are unlikely lovers in the film as well as unlikely actors to play the roles. Both are quite young, clean and used to be seen chasing older or younger women in their other films. However, their chemistry is unmatched and their talent makes the film work in devastating ways. Gyllenhaal uses his often-typecast character in new and interesting ways, making it one of his best films and best performances to date.

Jarhead– The film received most positive reviews from critics but was unfairly panned by mainstream audiences amidst Operation Iraqi Freedom. One of the strongest parts of the Sam Mendes film is Gyllenhaal’s performance as Swofford, a scout sniper who hasn’t fired a shot and comes from a long line of Marines. His harsh body and protagonist stature are opposite of his big boyish blue eyes and personality that is often pushed over by his fellow comrades and cheating girlfriend. Jarhead is one of Gyllenhaal’s films that put him into big boy status, as a man finally, similar to something his character goes through in the film.

Zodiac– The David Fincher film co-starring Robert Downey Jr. was a perfect role for Gyllenhaal, who was on a hot streak of great films following Brokeback Mountain. The film was given rave reviews, but was smothered at the box office and was slighted out of awards season due to its March release. As a naive political cartoonist that is summoned to help decode messages from the Zodiac killer, Gyllenhaal is just right and holds his own in a great cast.

Catch up on all these great Jake Gyllenhaal films at LOVEFiLM. With of 70,000 titles and counting you’re sure to find something to watch!