The Weird and Wonderful Jake Gyllenhaal

From Donnie Darko to Spider-Man, there is no such thing as a boring Jake G performance.

Jake G Spiderman

Since embarking on the Spider-Man: Far From Home press tour, Jake Gyllenhaal seems to have gone a little rogue. Certainly, Gyllenhaal has never been a dull or straightforward person, but over the past few weeks, the internet has been swarmed with eccentric and strange video clips of the actor. R. Eric Thomas of Elle astutely points out that Gyllenhaal “constantly hints at deep reserves of chaotic energy,” a point that stands both onscreen and off. Much like his sister Maggie, Jake has built a career on playing offbeat characters in well-respected indie movies, and Far From Home is perhaps the biggest budget film with the most mainstream appeal he has been involved with to date.

This wacky press tour demonstrates Gyllenhaal’s dedication to his craft and also confirms that he is a funny, strange, and charming weirdo. Gyllenhaal possesses the ability to immerse himself completely into a role, and while that does not always literally entail a physical transformation, it is evident that he connects deeply to his characters and alters his movements, mannerisms, and modes of speaking with each performance (including the one where he discusses the beginnings of Benedict Cumberbatch’s career).

One of Gyllenhaal’s most famous performances is in Richard Kelly’s spooky suburban sci-fi feature Donnie Darko (2001). Playing the titular role, Gyllenhaal broods and sleepwalks, vacillating between gentle sensitivity and being a troubled menace. Donnie stumbles dreamily through his life, faced with (possible) hallucinations and deep philosophical questions about time and the end of the world, topics that weigh heavily on a teenager from a sunny Virginia town. Gyllenhaal displays maturity and a strong sense of actorly self-knowledge in this role, traits that inform his performances even as he has grown and changed over the years.

After Donnie Darko, he starred in Bubble Boy (2001), an ill-fated and critically panned comedy. While the film is at times tasteless and awkward, Gyllenhaal plays Jimmy, a boy born with no immune system, with bright-eyed naïveté and a canny sense of comedy. These performance beats particularly emerge with his loud speaking voice, a result of his character spending most of his life inside a plastic bubble.

The following year, Gyllenhaal starred alongside Jennifer Aniston in The Good Girl (2002). As Holden, Gyllenhaal finally had the opportunity to demonstrate his skills as a romantic lead. His expressive face and reserved body language endear him to Aniston’s character, Justine, with whom he begins a disastrous affair. Gyllenhaal gives one of his most thoughtful, complex performances as Holden’s mental health begins to deteriorate and he becomes increasingly desperate to be with Justine. Even when things take a tragic and violent turn for Holden, Gyllenhaal’s performance elicits empathetic understanding toward this lovesick and inexperienced young man.

This performance filled with heartbreak, longing, and a struggle for self-understanding informs Gyllenhaal’s work in such movies as Brokeback Mountain (2005) and Love & Other Drugs (2010). In Brokeback, he plays Jack Twist, a sheepherder who begins a deeply passionate relationship with his co-cowboy Ennis Del Mar (Heath Ledger). Gyllenhaal and Ledger’s chemistry is undeniable, yet so is the torturous strain of denying their sexual and romantic connection in the face of strict conservatism and the specter of violent homophobia.

Gyllenhaal reunites with Brokeback‘s Anne Hathaway in Love & Other Drugs, another film in which he struggles to navigate a complex romantic relationship. Gyllenhaal plays an overconfident pharmaceutical sales rep, displaying a swaggering bravado that sets him apart from the restrained and troubled characters the actor had played up until this point. Gyllenhaal and Hathaway sparkle in the way they dance around, trying to avoid falling in love but unable to keep their hands off each other. Even in a fairly conventional romantic comedy, Gyllenhaal brings a unique and unpredictable energy.

With the films Prisoners (2013), Enemy (2013), and Nightcrawler (2014), Gyllenhaal began to turn toward portraying darker, more twisted characters. As Detective Loki in Prisoners, Gyllenhaal plays an isolated, obsessive man who nervously and compulsively blinks, and in scenes where he confronts dangerous criminals, his aggression toward them hints at a violent rage hiding beneath his nervous exterior.

This darkness housed within a gentle exterior reappears in Nightcrawler, in which Gyllenhaal plays Lou Bloom, a wannabe news cameraman. As Bloom ventures further into the dark side, tampering with crime scenes, stealing, and blackmailing news director Nina Romina (Rene Russo), his unassuming facade begins to crack, terrifyingly exemplified in the scene when Gyllenhaal aggressively yells at himself in the bathroom mirror.

In Enemy, Gyllenhaal plays two identical versions of himself. This film, based on José Saramago’s novel The Double, displays Gyllenhaal’s ability to subtly and meticulously differentiate his characters. Adam, a professor, and Anthony, a struggling actor, lead very different lives, and Adam is closed-off and nervous where Anthony is confident and laid-back. What makes this movie terrifying is the way their lives seamlessly intersect, with Anthony’s wife Helen (Sarah Gadon) barely able (or willing) to tell the difference between the two men, and Adam’s mother (Isabella Rossellini) mentioning conversations she has had with Anthony. Gyllenhaal brilliantly embodies the quiet horror of discovering that you may not be who you think you are.

Gyllenhaal’s more recent roles have taken this darkness and combined it with the more lighthearted strangeness of his earlier films, leading to oddball characters such as the corporate zoologist Dr. Johnny Wilcox in Okja (2017) and the dandy art critic Morf Vandewalt in Dan Gilroy’s Velvet Buzzsaw (2019). With these performances, Gyllenhaal delights in playing slightly disturbed, slightly brilliant characters who never quite decide between being good guys or bad guys but instead traverse moral grey areas with great enthusiasm.

Yohana Desta of Vanity Fair writes that Gyllenhaal’s previous roles demonstrate his particular ability to play unhinged characters and that his latest performance as Mysterio in Spider-Man: Far From Home takes him right to “the peak of Mt. Unhinged.” Indeed, Gyllenhaal dramatically swoops between being supportive and kind with Peter Parker (Tom Holland) and then maniacal and obsessive while working on his own schemes. Mysterio could not have been played better by any Hollywood actor, with his dramatic gestures and flashes of villainy. Even a cursory look back at Gyllenhaal’s career makes it clear that he approaches every character with this unique brand of enthusiastic strangeness.

Actual film school graduate. Perpetually sleepy.