Jake Gyllenhaal’s 10 Most Iconic Roles, Ranked

Jake Gyllenhaal is a rare creature in Hollywood. A leading man, able to support the massive weight of tentpole franchises, but also a proven character actor, able to transform and disappear completely into his roles. His career is markedly varied, veering into the mainstream just long enough to surprise with a sharp left turn into more artistic pursuits. Although an indie darling, Gyllenhaal seems to fit as comfortably into the world of action blockbusters as he does intimate family dramas. Not to mention the occasional sojourn into a Broadway musical. Ever since his first big-screen appearance, almost twenty years ago now, Gyllenhaal has subverted expectations. It’s no wonder then that his credits reflect his versatility and his ability to chose projects out of left field.

What sets Gyllenhaal apart even further is his undeniable charisma and relatability. Whether he’s playing a nefarious reporter, a troubled teen or comic book villain, it is always a pleasure to watch Gyllenhaal work. Perhaps it’s his wide-ranging choice of roles and projects or his watchability factor that has resulted in so many iconic performances. Either way, ‘iconic’ is an apt way to describe most of Gyllenhaal’s roles. So here are 10 roles we thought were the most iconic.

10 HOMER HICKMAN – OCTOBER SKY

October Sky was released in 1999 and introduced the world to Jake Gyllenhaal. Despite a few TV credits to his name, this was Gyllenhaal’s breakthrough role. And what a breakthrough it was. Not many actors get to star alongside talents such as Laura Dern and Chris Cooper on their first outing. Gyllenhaal’s portrayal of Homer, a boy determined to take up rocketry despite his father’s misgivings, showed signs of the depth and charm Gyllenhaal would come to be known for.

9 MORF VANDEWALT – VELVET BUZZSAW

Throughout his career, Gyllenhaal has navigated the thin line between ‘boy next door,’ and ‘full-on creeper’ and this role is a great example of that dichotomy. While not universally beloved, this Netflix film was a campy and violent portrayal of the art world, in which Gyllenhaal gave a pitch-perfect portrayal of a self-possessed, pretentious art critic.

One of his whackier, more overt performances, this role proves Gyllenhaal’s versatility and ability to give credence to less grounded, broadly comic characters.

8 JOHNNY WILCOX – OKJA

Staying logged into Netflix for this next one. Okja is as sweet as it is bizarre and seemingly a perfect fit for Gyllenhaal. Here we can see him at his most over the top; hamming it up to the maximum degree.   Although, one of his lesser-known roles, this one made the list due to its complete lack of subtly. A great example of Gyllenhaal going to town on the scenery, filling every frame and probably having a great time while he does it. This role proves he’ll go the extra mile in any role, even one so unlikable as Johnny Wilcox.

7 ANTHONY SWOFFORD – JARHEAD

Speaking of sharp left turns. Gyllenhaal’s role as marine sniper Anthony Swofford was the first time we saw him playing a role this naturalistically. Much of the dialogue in this film was improvised allowing for extra realism.

Despite already having made a name for himself, Jarhead was an integral role for Gyllenhaal’s career, showcasing his ability to play subtle and allowing him to move into more adult characters.

6 COLTER STEVENS – SOURCE CODE

The role of Colter Stevens in Source Code is iconic as it’s exemplary of a blending of genre, theme and style pertinent to Gyllenhaal’s career. The film itself is part of an early 200s trend in film making which tackled experimental sci-fi themes, mixing in some action, realistic performances and addressing the current climate surrounding warfare and terrorism. Gyllenhaal has often taken roles which have explored science fiction in real world settings, grounding the genre and his performance.

5 JEFF BAUMAN – STRONGER

Jake Gyllenhaal has expressed in interviews how important this role was to him. In this film he plays a victim of the Boston Marathon bombings, Jeff Bauman, who after loosing both his legs due to injuries caused by the attack, was able to give a description of the bomber to the FBI and aid in his capture. It’s a true to life story and one which Gyllenhaal obviously felt a strong responsibility to bring to people’s attention, exemplifying Gyllenhaal’s passion for choosing roles with greater depth and meaning.

4 QUENTIN BECK – SPIDER-MAN: FAR FROM HOME

Perhaps the most interesting thing about Jake Gyllenhaal appearing in a Spider-man film is the full-cycle-ness of it all. Infamously, Gyllenhaal almost donned Spidey’s cowl for Sam Ramie’s Spider-man 2 after Tobey Maguire injured his back. However, Maguire recovered and Gyllenhaal would have to wait until 2019 to enter the Spider-verse, albeit this time as a villain. This role is iconic for a number of reasons. Yes, Gyllenhaal is finally in a Spider-man film but more-so it represents a return to big-budget blockbuster film making, something Gyllenhaal has been somewhat absent from since the poorly received Prince of Persia in 2010.

This is Gyllenhaal’s entry into the MCU and it’s also the first time film audiences have seen Mysterio on screen. Gyllenhaal has received positive feedback for his performance and even more positive feedback for his antics with Tom Holland on the press tour. This role has launched Jake Gyllenhaal back into the mainstream conversation. He’s also responsible for a pretty spoiler-y twist, which will really shake things up for the Spider-Man franchise moving forward.

3 LOUIS BLOOM – NIGHTCRAWLER

Perhaps Gyllenhaal’s greatest transformation, his role as Louis Bloom in Nightcrawler saw the actor lose a tremendous amount of weight, which coupled with a completely immersive performance proved just how committed and talented Gyllenhaal is. His rendering of the character was so complete that audiences were able to lose sight of the familiar actor, instead focusing on the entirely creepy Bloom, an ambulance chaser looking to make money by selling footage of crimes and road accidents. This role also marks the start of Gyllenhaal’s move towards playing less likeable, villainous characters.

2 JACK TWIST – BROKEBACK MOUNTAIN

This is the role that truly put Jake Gyllenhaal on the map. Brokeback Mountain is historic for its portrayal of a gay romance between cowboys in a major motion picture and for casting two leading Hollywood actors in those roles. Gyllenhaal’s performance is heartfelt and earnest and earned him an Oscar Nomination.  The performances in this film, the artful direction and the subject material launched this film in the world’s eye and Gyllenhaal along with it. It will surely be remembered as one of his most outstanding achievements as an actor.

1 DONNIE DARKO – DONNIE DARKO

Finally, Gyllenhaal’s most iconic role is inescapably the title role from Donnie Darko. Despite an underwhelming reception upon its original release, Donnie Darko has gone on to gain an extensive cult following. Not only will Gyllenhaal be associated with this role for a very long time, it propelled his career forward while also introducing a number of themes which would pervade his entire career. The exploration of science fiction as seen through a grounded, humanistic lense continues to be a running theme in Gyllenhaal’s career along with endearing yet haunted characters. Donnie Darko really marks the start of Jake Gyllenhaal’s career and trajectory leading to such roles as Louis Bloom and Mysterio today.