A creepy journalist, a soldier and a burnout detective – welcome to the list of best performances of Jake Gyllenhaal.

Jake Gyllenhaal has been a quality indicator for a long time now and he’s been one of the most solid Hollywood stars too.

And while I’m still not a fan as big as to call myself a Gyllenhaalic (as his die-hard fans like to call themselves apparently), Jake belongs to a minority of actors, who – even when starred in a more-bomb-than-not films – save face nevertheless.

He started acting at the age of 11, playing a small role in a movie called City Slickers (1991). At a young age, Gyllenhaal scored a career-turning role in Donnie Darko (2001), which elevated him to one of the hottest prospects in the City of Dreams. From now on, he navigated the waters of Hollywood without a miss.

In this list, I looked at his best works up to date, trying to capture the incredible range of his roles, proving the versatility that defines the blue-eyed starboy. See if you agree with the choices of Cultural Hater!

#12 Jake Gyllenhaal as Douglas Freeman in Rendition (2007)

Rendition (2007) wasn’t the most wildly successful movie starring Gyllenhaal, but his role deserved to open the list of his best performances. Why?

Because that’s exactly the role, where despite given a mediocre role, Jake managed to leave a footprint.

Gyllenhaal plays a negotiator, who tries to bring an innocent man back to his family, after he’s kidnapped in the Middle East. In a plot, where character development shifts toward the victim and its family circles, Gyllenhaal finds a way to squeeze in with a genuine role of a man, who – apart from being professional – connects to the case on a more personal level.

In Rendition (2007), Gyllenhaal blended in the whole story in the supporting role that allowed the film’s main characters to take over and remain in the spotlight. It was also one of the roles that showcased his true zeal that fueled Gyllenhaal’s forthcoming performances, later in his career.

#11 Jake Gyllenhaal as Jack Twist in Brokeback Mountain (2005)

Don’t freak out over Brokeback Mountain (2005) taking only the 11th spot on the list.

As a whole, Brokeback Mountain (2005) didn’t age well and after more than a decade, Ang Lee’s Oscar-winning drama is a far cry from we all initially believed it was. Despite my view of Brokeback Mountain (2005) as an overrated movie (despite its socially important premise), the duo Ledger & Gyllenhaal was on spot.

The latter found his “softer” side, striking a perfect balance between an over-the-top cowboy and a man whose afraid of his own self (and the reaction of his environment toward it too). People tend to see Ledger as the main star of Brokeback Mountain (2005), but I’d say their mutual chemistry elevated Ang Lee’s story to a triple Oscar winner.

#10 Jake Gyllenhaal as Morf Vandewalt in Velvet Buzzsaw (2019)

The second collaboration (after Nightcrawler in 2014) of Dan Gilroy and Jake Gyllenhaal resulted in a horror satire, where the actor had a much lesser role to play in comparison with their first on-screen get-together. The film fiddles with concepts of the over-the-top world of modern art and greed associated with it, but although it’s a clever blend to start with, “Velvet Buzzsaw” lacks enough depth to be more than just a decent Netflix movie.

Morf Vandewalt is an art critic, a being built out of stereotypes – from the way his body speaks to the way he thinks and spits cringy bollocks during exhibitions, Gyllenhaal’s take is a joy to watch. He genuinely likes the character, clearly having fun with its pretentious approach. Vandewalt, however, falls prey to the slightly inept script. It’s an underdeveloped character, which runs out of steam after revealing its one-liners and sarcas to be its only trademarks.

Nonetheless, Morf proves Gyllenhaal’s rare ability to immerse in a character and build it with an eye for detail. It’s much more visible in roles you’ll see later on in this article, but – as the pretentious art critic – Gyllenhaal played out great.

#9 Jake Gyllenhaal as Jerry Brinson in Wildlife (2018)

One of the things that characterize a great actor is an understanding of the place of a character in a greater scheme of things. The stars and starlets usually crave attention, but letting someone else shine and nailing your supporting role at the same time – that’s a real challenge.

In Wildlife (2018), the directorial debut of Paul Dano, Gyllenhaal plays Jerry Brinson – a withdrawn, absent-minded husband of Jeanette, marvellously portrayed by Carey Mulligan.

Wildlife (2018) is Mulligan’s grand spectacle. The story’s told from her perspective, a woman locked in the role that both society and her husband expect her to play. She’s mesmerizing, bouncing from anger and bitterness to flirtatiousness in a split of a second.

Gyllenhaal serves as a contrast, much needed in the presence of sharpened, a bit feminist Mulligan. Jerry is one of the types of roles that Gyllenhaal likes to choose too. Often perplexed, left aside with all his unresolved mysteries, Jerry’s unable (and uninterested in doing so) to fix his marriage, which then pushes him to leave his wife and son.

There isn’t much screen time for Gyllenhaal to grab spotlight all to himself, but Dano’s skillful direction placed the actor where his role helps to define Mulligan’s protagonist – instead of fighting her.

#8 Jake Gyllenhaal as Anthony Stafford in Jarhead (2005)

Jarhead (2005) tells the story of Anthony Stafford, a U.S. marine soldier, who’s sent to Saudi Arabia during 1980s. Stafford’s 175 days of boredom are filled with everything but war, while the few days of service during the Gulf War are a traumatic event that he can’t cope with.

Jarhead (2005) was Sam Mendes’ equivalent of Kubrick’s Paths of Glory (1957) or Malick’s The Thin Red Line (1998) – a war-themed drama depicting the horrors of an unspeakable tension, fear, death and hopelessness.

Jarhead (2005) is much different from most roles Gyllenhaal played in his career. Stafford isn’t overly complex until the circumstances begin to shape him otherwise. Observing Gyllenhaal’s like seeing clay folded into a horrific statue, as the character’s primal instincts are awaken over the course of the movie. There is power to Anthony Stafford and a significant, dramatic role at stake here – one that’s been a first important sign of Gyllenhaal’s appetite for more.

#7 Jake Gyllenhaal as Donnie Darko in Donnie Darko (2001)

Many people instantly connect Jake Gyllenhaal with Donnie Darko (2001), his breakout role from 2001. While it’s understandable, a certain perspective (meaning almost two decades passed) gives grounds to a belief that Gyllenhaal has a lot more to offer.

In Donnie Darko (2001) Gyllenhaal played a confused teenager, who envisions a creepy rabbit, that follows him everywhere he goes. The film belongs to the “mindfuck” genre, spawning hundreds of threads on reddit and heated discussion between various audiences, debating on what actually happened in the series of complex events. It’s a movie that plays with the viewer in an uncanny way and Gyllenhaal finds himself swimming in its abstract waters.

As Donnie Darko, Gyllenhaal exposed his ability to lurk into some dark places, drawing inspiration from both horror and thriller. Donnie isn’t a regular teenager, but instead – the kind of kid that peers steer away from. One can also see that it was the kind of role that Gyllenhaal enjoys the most – the best of his performances were actually the creepiest.

#6 Jake Gyllenhaal as Brian Taylor in End of Watch (2012)

Gyllenhaal’s impressive span of roles points to his talent, but also the chameleon skin he wears. In a way, Gyllenhaal deploys techniques of method acting, throwing himself entirely, which helps him derive parts of character from the background a certain character lives in.

The film, directed by David Ayer, is a genuine documentation of the struggle of being a police officer in America – the topic more and more often used and discussed in cinema nowadays.

That’s also the case of Brian Taylor, a street cop patrolling LA. The grit of Taylor is on par with Manuel Pena’s phenomenal role (the Mexico-born partner of Taylor), and the two solidified the documentary-like vibe flawlessly. For a film so deeply immersed in its own authenticity (rumor had it both actors worked with real cops for weeks before arriving on set) that any false tune in either character would jeopardize the entire operation.

In End of Watch (2012) Gyllenhaal tackles the role of the tough guy (which gave grounds to his performance in Southpaw too), but also a hot-headed rookie cop assigned to the wrong neighborhood. He mixes chutzpah and an attitude of being green behind the ears, which results in a memorable, very honest performance.

#5 Jake Gyllenhaal as Davis in Demolition (2015)

Demolition (2015) was a victim of poor marketing, and a great pity that was, because it’s one of Gyllenhaal’s most intriguing and highly unexpected turns.

Davis, the protagonist of Demolition (2015), loses his wife in a car accident and – as a form of greed-releasing tool – he begins to form a peculiar pen-pal kind of relationship with a sales rep, whom he writes to.

In Demolition (2015), Gyllenhaal showcases an intelligent approach to a character that could easily be flattened and plain. Davis’ motive to lose his spine is obvious and so is Jean-Marc Vallee’s story. Despite a simple story, Gyllenhaal – with a great help of Naomi Watts’ genuineness – keeps the viewer glued to the screen. The actor finds a twisted side to Davis, the unease that makes him much more interesting than the story initially suggests.

#4 Jake Gyllenhaal as Robert Graysmith in Zodiac (2007)

Even until this day, David Fincher’s Zodiac (2007) is one of the most groundbreaking thrillers in history. The depressingly bleak colours, an inadvertently hopeless investigation and a frustrating awareness of Zodiac’s masterful game he plays over the years – they all turned this 2007’s movie into a benchmark for all modern thrillers and crime dramas.

As it usually takes place in Fincher’s films, Zodiac (2007) too features a stellar cast that this time includes Robert Downey Jr., Mark Ruffalo, Chloe Sevigny and Anthony Edwards. This ensemble also features Jake Gyllenhaal as Robert Graysmith, the author of a novel that “Zodiac” is based on.

As Robert Graysmith, Gyllenhaal perfectly blends into the harrowing tone of Fincher’s film. In the tiring investigative tone, Gyllenhaal gives a marvellous performance as a relentless journalist, whose dedication to help finding the killer-on-a-loose turns into an obsession. Gyllenhaal’s character evolves over the two-and-half hours, exploring a man throwing his entire life into the lucid dream, shared and eventually forgotten by the investigators he supports.

Gyllenhaal’s role in Zodiac (2007) explored a different kind of his acting palette, that the actor put into motion (and mastered) in Nightcrawler (2014) – a maniacal individual that pushes his own boundaries.

#3 Jake Gyllenhaal as Detective Loki in Prisoners (2013)

While it’s not the top of the list (simply because there were two more astonishing roles of his), Gyllenhaal in Prisoners (2013) put his heart and soul into constructing the most intriguing character in the film and one that stayed with after all these years since its premiere.

Detective Loki is a box of mysteries, that Aaron Guzikowski (the screenwriter of Prisoners (2013)) keeps in the mist of unknown. Loki develops a very personal connection to the case of a kidnapping of two young girls. He’s a loner, and a person, who clearly loses his temper as the investigation drags on.

Gyllenhaal is incredible in the most unexpected moments in Prisoners (2013). As Loki, he captures the mix between a solemn loner and character that you genuinely root for. The meticulous approach is visible in Loki’s appearance – signet on his finger, shady tattoos and a tick that, over the course of the film, becomes the character’s trademark. Interestingly, Gyllenhaal added a lot of these elements as his own dowry, building on top of the incredibly intense script.

In the film’s brooding mood and within the dark topics touched, Detective Loki’s character not only complements Villeneuve’s vision, but becomes one of the pillars of the plot.

#2 Jake Gyllenhaal as Adam & Anthony in Enemy (2013)

Enemy (2013) offers a double-barrelled version of Jake Gyllenhaal, which technically means two roles.

In this Denis Villeneuve-directed thriller (based on a novel by Jose Saramago), Gyllenhaal plays Adam – an ordinary guy, who after renting a movie on a lonely night, spots his doppelgänger named Anthony. He then decides to find this man and unravel a terrifying mystery surrounding him.

I often like to mention Enemy (2013) as one of the most criminally underrated films of the 21st century. It’s Denis Villeneuve’s most complex, disturbing and atmospheric film, drenched in bleak yellowish colours and conjuring a truly unforgettable story, which went entirely off radar – both audiences and awards-wise.

The uncompromising direction needed someone versatile and I honestly couldn’t imagine someone more suited for this role than Gyllenhaal.

As Adam, Gyllenhaal loses himself in a slow process of a maniac being born. Adam fuels the story, as a mix of a protagonist and antagonist in one. Anthony, on the other hand, is lured into a situation that he finds unprecedented, at the same time losing his way of escaping the rope tightening around his neck. In this double stunt, the actor draws a thick line between the two characters, making up for a delicious spectacle.

Enemy (2013) was the first sign of Gyllenhaal’s fascination with adrift characters, complicated and difficult to pull off. Given a riveting story and Villeneuve’s visionary direction, Gyllenhaal managed to carry the weight of a bonafide head-scratcher on his own shoulders (each one times two).

#1 Jake Gyllenhaal as Louis Bloom in Nightcrawler (2014)

If any year could be called Jake Gyllenhaal’s pinnacle, it has to be 2013 (and part of 2014). With Prisoners (2013) and Enemy (2013) already mentioned on that list, Dan Gilroy’s Nightcrawler (2014) marked Gyllenhaal’s most prominent, scariest and dangerously good role so far.

Louis Bloom is a self-appointed journalist, who dreams of getting a job in one of the news channels. We get to know him as a desperate-for-work creep, ready to get any kind of job.

Over the course of the whole film, Dan Gilroy paints a terrifying image of journalism, where predators like Reed – ready to sacrifice everything – sniff the tragedy of others and build their success with blood on their hands.

But Nightcrawler (2014)cuts so deep thanks to Jake Gyllenhaal’s masterful performance. Louis Bloom is a calculating, horrifying human being, who knows no boundaries in order to become succesful. Gyllenhaal incorporates a little over-the-edge attitude, but that’s what elevates Lou to a level of an experience, rather than just a character itself. Everywhere he appears, everywhere he acts, there is a scent of something fatal, something horrifying – end justifies the means.

It was a role that defined Gyllenhaal’s career and if he ever deserved an Oscar in his life, that’s his deserved moment of should-have tryumf.

What’s your favorite role of Jake Gyllenhaal? Which role would you add to the list? Blast off in the comments below!