The Gyllenhaals have become a Hollywood institution over the last decade; both Maggie and her brother, Jake, have proven themselves time and time again to be reliable forces in the films they inhabit. In honor of Jake Gyllenhaal’s recent release, “Southpaw,” let’s take a look back at some of the actor’s best performances to date.


Jake Gyllenhaal in "Prisoners"


5. Detective Loki – “Prisoners”

In the criminally underrated “Prisoners,” Gyllenhaal plays detective Loki, a dedicated detective charged with finding a missing girl. The actor imbues the character with a sense of untouchability and hypermasculinity that not only deviates from his somewhat sensitive public image, but makes his few emotional outbursts that much more terrifying.



Jake Gyllenhaal and Heath Ledger in "Brokeback Mountain"


4. Jack Twist – “Brokeback Mountain”

As one of a pair of star-crossed cowboy lovers, Gyllenhaal earned himself an Oscar nomination, which he ultimately lost to George Clooney. Regardless of the loss, in this role, Gyllenhaal proved himself to be much more than just a young heartthrob in a controversial film about forbidden love. On top of all of that, he also coined the classic line, “I wish I knew how to quit you.”



Jake Gyllenhaal in "Southpaw"


3. Billy Hope – “Southpaw”

The most recent entry on this list, Gyllenhaal completely transformed himself — inside and out — for the role of Billy Hope: a down on his luck light-weight boxing champion. Interestingly enough, the role of Billy Hope was originally intended for Eminem, but Gyllenhaal brought a raw physicality to the role that completely convinces the audience of his harsh upbringing.



Jake Gyllenhaal in "Donnie Darko"


2. Donnie Darko – “Donnie Darko”

A cult classic, “Donnie Darko” is the film that really introduced Gyllenhaal to the world as a viable onscreen talent. As a teenager in the throes of puberty, Donnie survives a bizarre accident involving an airplane, only to discover he has the ability to alter time itself. The film takes a fairly familiar, even idyllic, American setting and warps it into a creepy nightmare; Gyllenhaal’s portrayal of the titular teenager barely holding onto reality serves as the grounding performance of the film.



Jake Gyllenhaal in "Nightcrawler"


1. Lou Bloom – “Nightcrawler”

It couldn’t have been anything else; the fact that Jake Gyllenhaal did not receive an Oscar nomination for his turn as “photojournalist” Louis Bloom in 2014’s “Nightcrawler” is an absolute travesty. Scrawny, slimy, and generally disagreeable, Gyllenhaal brings a fake charisma to the character that often times even charms the audience, even though we know right off the bat that we dislike him. He’s a character who feels nothing, understands that modern Americans wish to be shocked, and will do anything to get his shot at glory. If Travis Bickle from “Taxi Driver” read every self-help book ever written — and then committed them all to memory — you would have Lou Bloom.


Are there any performances we missed? What is your favorite Jake Gyllenhaal film? Comment below or tweet @connerws to tell us what you think!