Jake Gyllenhaal: From acclaimed dramas ‘Donnie Darko’ and ‘Brokeback Mountain’ to ‘Road House’ action

During a joint TV interview to promote Spider-Man: Far From Home, Tom Holland (Spider-Man) and Jake Gyllenhaal (the villain) were asked which director they would like to work with in the fall of 2021. Gyllenhaal answered: “Pedro Almodóvar.”

This was one of the last appearances by Gyllenhaal when he was still considered an art film actor, because in recent years his priorities have been testosterone-packed movies where he can show off his impressive physique, as in the remake of Road House, which premiered on Prime Video and is a film with the flimsiest of storylines revolving around fights. Such is the latest drift of an actor whose resume includes classics such as Donnie Darko, Brokeback Mountain, Okja and Nightcrawler, but who has recently been turning to filmmakers such as Michael Bay and Guy Ritchie. Why have his tastes changed, or has he always harbored a passion for biceps and brawls?

The success of Road House on Amazon Prime has been astounding: at the beginning of April, after its first two weekends, 50 million viewers had seen it, according to unspecified calculations made by the platform; at the end of May, that number has reached 80 million and, according to updated data from the Nielsen consulting firm, it is the most watched film on Prime so far this year. On the back of this triumph, the actor’s production company, Nine Stories, has signed a three-year agreement with Amazon MGM Studios, a contract that specifies that the studio will have first option on the fiction films that Nine Stories intends to produce both for movie theaters and streaming. Also to consider is that Gyllenhaal came to Road House after the initial development of the script by MGM; later, the studio and all its content was swallowed by the online sales platform.

Gyllenhaal’s previous role in Guy Ritchie’s The Covenant was also released under the Amazon MGM Studios umbrella, although it was initially in movie theaters. With Nine Stories, Gyllenhaal had already produced Antoine Fuqua’s The Guilty (2021) for Netflix, a remake of the Danish thriller in which he plays a cop who doesn’t move from the phone. Clearly, the actor has a firm grasp of how to work the new cinematic playing fields to his advantage: his next release will be the series Presumed Innocent, on AppleTV+ on June 12, in which he plays a Chicago prosecutor accused of a brutal murder. Sound familiar? Well, that’s because it’s the serialized version of the Alan J. Pakula film of the same name that starred Harrison Ford in 1990. Zero creativity. Yet another remake.

What is curious about all this is that LA-born Jacob Gyllenhaal, comes from a family very much rooted in auteur films. He is the son of director Stephen Gyllenhaal (Waterland, A Dangerous Woman) and screenwriter Naomi Foner (Running on Empty). His older sister, actress Maggie Gyllenhaal, is now a prestigious director (The Lost Daughter). Jake began his career at age 11, in City Slickers as the son of Billy Crystal, who met him at a dinner party at the Gyllenhaal’s home. After several performances in films and episodes directed by his father, he starred in October Sky in 1999, a drama based on a true story about a miner’s son who ended up designing rockets, making him an emerging actor to watch.

Apparently, Gyllenhaal auditioned twice to play Frodo in Lord of the Rings. In the first audition, he was not supposed to speak, just pick up the ring. Not understanding the symbolic value of the ring, his off-kilter performance drove director Peter Jackson to despair. Some time later, he went back to the director, with equally dissatisfying results: Jackson became angry when he heard Gyllenhaal recite the dialogue and told him he was “the worst actor in the world.” This might have had something to do with the fact that Gyllenhaal had not been told by his agents that he had to speak with a British accent. Another, less embarrassing rejection came for the role of Christian in Moulin Rouge! that was between Heath Ledger, with whom he would later star in Brokeback Mountain, and Ewan McGregor, who took the role. This despite director Baz Luhrmann’s remark that Gyllenhaal “is really a great musical artist.”

Those failures were offset by the success of Donnie Darko (2001), the quintessential teen melancholy drama that turned him into indie actor par excellence. His rise to stardom continued when he played Dennis Quaid’s son in the blockbuster The Day After Tomorrow, though it faltered when he lost the chance to play Batman in The Dark Knight trilogy – both Christopher Nolan and Baz Luhrmann actually called a grateful Gyllenhaal to explain why he had not been successful, as the actor explained during the promotion of Road House. But his upward trajectory regained momentum when he was chosen to star alongside Heath Ledger in Brokeback Mountain (2005), for which he won his only Oscar nomination. The love story between the two cowboys and Gyllenhaal and Ledger’s shared approach to it gave rise to a friendship between them that was cut short by Ledger’s death from an overdose of prescription drugs: Gyllenhaal is the godfather of Ledger and Michelle Williams’ daughter, Matilda.

Since then, Gyllenhaal has starred in all kinds of acclaimed movies, including Prisoners and Enemy directed by Denis Villeneuve, Jarhead by Sam Mendes, Zodiac by David Fincher, Demolition by Jean-Marc Vallée and Brothers by Jim Sheridan. He then began to veer towards action, although Southpaw – his first collaboration with Antoine Fuqua – didn’t work out. But at least it didn’t bomb like Prince of Persia: The Sands of Time in 2010, to the astonishment and pain of Disney. Gyllenhaal had never experienced anything like it, and even today he recalls the dimensions of the failure: in his children’s book co-authored by his best friend Greta Caruso, The Secret Society of Aunts and Uncles, illustrator Dan Santat depicts a person with a sign that ominously reads “The Persians” during 10-year-old Leo’s dance audition – a moment that Gyllenhaal recognizes as a low point for his protagonist, though he didn’t notice the detail until the book was out.

Throughout, Gyllenhaal continued to act in stage plays and came close to an Oscar with Nightcrawler in which he plays a stringer who records violent events late at night in LA and sells the footage to local TV stations. He then took risks in offbeat movies such as Okja (2017), by South Korean Bong Joon-ho that streams on Netflix; Nocturnal Animals, by Tom Ford, and Prisoners, by Paul Dano. With a beard, he looked older and more intellectual; without it, he appeared youthful and lighthearted. In the Spanish Pyrenees, he took photos in a Golden State Warriors jersey with the locals during the filming of the western The Sisters Brothers (2018), bonding with his creative team: director Jacques Audiard and screenwriter Thomas Bidegain. Few could have predicted what was to follow.

After The Sisters Brothers, Gyllenhaal steered clear of serious cinema. With Spider-Man: Far From Home, he threw himself into projects that revolved around shootings and fights. And then there were the remakes. The only time it seemed that the indie Gyllenhaal was going to bounce back with a role in Bidegain’s Suddenly, he himself abandoned the project.

The offer to play opposite Vanessa Kirby in the English adaptation of the French novel Soudain seuls, came during the Covid lockdown. Suddenly tells the story of a couple struggling to survive on an island while enjoying the trip of their dreams. For a year, via Zoom, Gyllenhaal and Bidegain polished the script in collaboration with David Lindsay-Abaire, and the actor joined the production team.

In Variety, Bidegain explains, “We had just done a new version of the script that incorporated the latest changes, and I did a lot of Zooms with Jake and Vanessa, so I thought the three of us were on the same page. So when we met in Iceland, I assumed that we would just put the finishing touches on it.”

With eight weeks to go, the three got together in Iceland, which is where the dynamics fell apart. Gyllenhaal had an epiphany during a walk in which he encountered a horse and decided that “it shouldn’t be a film about love, but a film about love of nature.” Bidegain says Kirby, for her part, insisted that the film have a more definite feminist edge with a radical ending. The screenwriter says his vision for the film was somewhere in the middle: “It’s a film about love, but also about love of nature, and it does have a strong female character.”

On the fourth day, Bidegain returned to Paris, shot the movie with French actors on half the budget, and released it in France last December. In Variety, Bidegain insists the problem was that he had never worked with an actor who was also a producer. “It’s a very strange experience when you work with an actor-producer who doesn’t have the same vision as the director: in France, the director is the one in charge of telling the story; and he’s in charge of the script, the set design, etc.” Interestingly, this is something Gyllenhaal might have grasped as he has been living in Paris for several months a year for some time now because of his relationship with French model Jeanne Cadieu.

In the U.S., Gyllenhaal makes headlines for his relationships: in 2009, he and Taylor Swift were a couple for three months. The breakup inspired Swift’s song All Too Well, from the album Red, which was released in October 2012. In November 2021, Swift released a remastered edition of Red with an extended version of the track and a video short, directed by Swift herself, in which actor Dylan O’Brien is a carbon copy of Gyllenhaal. A wave of rage against Gyllenhaal flooded the internet for weeks.

In a profile on Gyllenhaal in Esquire in March 2022, Villeneuve said, “Jake is definitely happier, more at peace.” And Fuqua stated he was “much calmer, a little more open” and seems “to be having more fun. And I think that’s maturity.” That may be why he wants to appear in more playful movies: his next release will be the action thriller In The Grey, directed by Guy Ritchie. Later, in spring 2025, Gyllenhaal will play Shakespeare’s villain Iago to Denzel Washington’s Othello in the Shakespeare play of that name, which will be Gyllenhaal’s third Broadway production. So at least his love of theater endures.

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