Jake Gyllenhaal might just be one of the most popular people in Hollywood.
The 42-year-old actor has spent most, if not all, of his life surrounded by the strange world of show business: His father is director Stephen Gyllenhaal, his mother producer and screenwriter Naomi Foner, and his sister of course, actor Maggie Gyllenhaal.
From 2001’s cult classics Donnie Darko and Bubble Boy, to Oscar-winning love story Brokeback Mountain, to rom-coms like Love & Other Drugs and superhero film Spider-Man: Far From Home, Gyllenhaal has a long and varied filmography and one look at his social media shows how he has collected a solid, supportive group of friends along the way.
Brokeback Mountain official trailer. Post continues below video.
Jake Gyllenhaal’s Hollywood genes.
Gyllenhaal is not only Hollywood royalty, he also has links to Swedish nobility through his father.
Despite growing up surrounded by fame, Gyllenhaal recalled how his parents wanted him to be grateful for his privileged lifestyle, insisting that he have summer jobs to support himself. He worked as a lifeguard and as a busboy at a restaurant operated by a family friend.
Born and raised in Los Angeles, he can count some very famous names as Godparents, including Jamie Lee Curtis and the late Paul Newman.
He recalled growing up as a sensitive child in an interview with British Vogue.
"I remember being very young, very sensitive, and someone said I was a doormat," he laughed. "I think what they were trying to say, that's full of its own very interesting complications, was that I cared. And things affected me."
He said he was grateful for how close he was with his family.
"I have been raised by a wonderful father who was always affectionate," he said.
"My mother and my sister are some of the most extraordinary people I know. Our vulnerability with each other, our ability to communicate about how tough times can be is what I'm most proud of in my family. For everything I hope to pass on, that's the most important.
"My mum always would say she saw me as a certain type of kid and she wanted to protect that. And admittedly, as much as they messed certain things up, they spent a great deal of time protecting that thing, that sensitivity, I think. I'm glad for that."
He also spent two years studying Eastern religions and philosophy at Columbia University, but dropped out before finishing his degree to focus on acting.
Jake Gyllenhaal's famous friendship group.
Tom Holland, brother-in-law Peter Sarsgaard, Ryan Reynolds and Hugh Jackman (he regularly gets himself involved in their 'feud') are among his tight-knit friends, which also included Heath Ledger before his death in 2008.
In April 2020, Gyllenhaal told fashion magazine Another Man, Ledger refused to present at the 2006 Academy Awards, due to a joke written into the award show’s opening ceremony about their film Brokeback Mountain.
"I remember they wanted to do an opening for the Academy Awards that year that was sort of joking about it," he recalled. "And Heath refused. I was sort of at the time, 'Oh, okay… whatever.' I'm always like: it's all in good fun. And Heath said, 'It's not a joke to me – I don't want to make any jokes about it'.
"That's the thing I loved about Heath. He would never joke. Someone wanted to make a joke about the story or whatever, he was like, 'No. This is about love. Like, that’s it, man. Like, no'."
In a 2018 interview with GQ Australia, Gyllenhaal reflected on the friendship he formed with Ledger, which led the 10 Things I Hate About You star to turn down a role in one of Baz Luhrmann’s films.
As he explained to the magazine, before they starred in Brokeback Mountain together, both Gyllenhaal and Ledger were vying for the lead role in Moulin Rouge.
The role ended up going to Ewan McGregor.
"We would be shuffled in and out of rooms. They would literally put me in a room and lock the door and Heath would come in and then Heath would be shuffled through the door. I never saw him," Gyllenhaal explained.
"When Ewan was cast, I finally met Heath and we sort of became friends before Brokeback Mountain, based on our mutual frustration.
"When Brokeback Mountain came out and it got all the attention it did, I remember, a few months later, Heath called me and he was like, [affects Ledger impersonation] 'Hey mate, I got some news for you.' I said, 'What?' He said, 'Baz just offered me his next movie. I just wanted you to know, I f***ing turned it down!' ... So that was how much Heath loved me, you know'."
Speaking to British Vogue about his famous friendships, Gyllenhaal visibly welled up.
"You're making me feel very emotional about my friends," he told reporter Olivia Marks. "Those male friendships are very important to me."
Jake Gyllenhaal's immensely private relationships.
Gyllenhaal is known for being very private, especially given his past relationships with some of the world's most famous women, including Kirsten Dunst, Reese Witherspoon and Taylor Swift (after which he and a now infamous scarf inspired what is considered by critics to be the greatest songwriting of her career, in 'All Too Well').
In 2002, Gyllenhaal was introduced to Dunst by his sister, who was her Mona Lisa Smile co-star. It was a young Hollywood dream; he was the next big thing, and she had just starred in Spider-Man.
They moved quickly, sharing a home in Los Angeles and adopting a puppy together.
In July 2004, they went their separate ways, with Gyllenhaal's rep saying they "remain the best of friends" (although in 2009, Dunst told Allure they weren't close).
Gyllenhaal was then linked to Natalie Portman, who he remained tight with. In 2011, he presented her with the Desert Palm Achievement Award, joking, "She's a vegan, which makes it really frustrating when you're picking a place to eat".
He then went on to describe Portman as "the Audrey Hepburn of our generation. She's graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind and Jewish".
In early 2007, Gyllenhaal began dating his Rendition co-star Reese Witherspoon.
In 2008, she described him as "very supportive" in an interview with Vogue.
"Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life. I am very blessed in that way."
Gyllenhaal was often photographed with Witherspoon and her two kids, Ava and Deacon, and would often cook for his girlfriend.
"Jake is a great cook," Witherspoon told InStyle. "He does a lot. We spend the weekends outside L.A, in Ojai, where I have a farmhouse. We have chickens and we grow cucumbers and tomatoes. I love it."
They split in 2009 but there was no bad blood. In fact, Gyllenhaal had nothing but nice things to say about his ex in 2016.
"She is, as I would say about most of the women who I'm close friends with or had relationships in my life, one of the smartest, strongest people I've ever met," he told Entertainment Weekly.
In 2010, Gyllenhaal, then 29, had a short-lived, but highly publicised relationship with a 20-year-old Taylor Swift. Paparazzi images of the couple walking arm-in-arm in New York with their maple lattes are now part of celebrity folklore.
In 2012, Swift released her fourth album Red, which included many Gyllenhaal references including 'All Too Well', 'We Are Never Ever Getting Back Together' and 'The Moment I Knew', about how Swift knew their relationship was over after Gyllenhaal failed to turn up to her 21st birthday.
In November 2021, Swift released the re-recorded Red (Taylor's Version), the second release in her plan to re-record all the albums she does not own the masters of, which once again sparked intrigue into their past relationship.
She also announced the release of All Too Well: The Short Film, based on a previously unreleased 10-minute version of the fan favourite song.
The film stars Sadie Sink, 19, and Dylan O'Brien, 30, which led to a re-examining of Swift and Gyllenhaal's relationship and age-gap.
After Swift, Gyllenhaal was linked to Anna Kendrick, and dated model Alyssa Miller in 2013.
In 2015, Gyllenhaal admitted to Howard Stern he'd been in love twice in his life.
When asked why he hadn't yet settled down, Gyllenhaal said "I think I probably just got scared… There are a lot of beautiful women, there are opportunities, but I think at the same time, if you find the right person, I believe in monogamy, I believe in when you meet somebody who is right it will be right and you will stay there."
Since 2018, he has been in a relationship with French model Jeanne Cadieu, 25.
They made their red carpet debut in September 2021 at the New York Film Festival.
"I've turned to love."
For decades, Gyllenhaal has been focused on his work; he's renowned for going deep, perhaps even above and beyond.
For his role in 2014's Nightcrawler, he dropped almost 14 kilograms and barely slept to transform himself into his character. He ran further than a half marathon a night to play a champion boxer in Southpaw.
But while many actors having dream roles, Gyllenhaal told Vanity Fair he doesn't work like that.
"I've never really worked like that. In fact, I'm more of the philosophy that the target draws forth the arrow, and if you listen clearly enough the things will reveal themselves... It's a much more strange, ephemeral, abstract process for me.
"Some actors will be like, 'I've always wanted to play this part.' I love interpreting and sometimes those things just come and you go like, 'Yes. That's what I'm looking for.' I have no idea what that will be."
In the same interview, in which he was promoting a new Prada fragrance, he shared that he was among an increasingly large group of celebrities who did not regularly... bathe.
"More and more I find bathing to be less necessary, at times," he said.
"I do believe, because Elvis Costello is wonderful, that good manners and bad breath get you nowhere. So I do that. But I do also think that there's a whole world of not bathing that is also really helpful for skin maintenance, and we naturally clean ourselves."
In 2020, Gyllenhaal shared that he's not just beyond... bathing. He's also interested in life beyond showbiz.
"I'm interested in my life, even more so than my work. I've reached a point in my career where I feel hungry in a different way. I've seen how much of my life I've neglected as a result of being committed to that work and that idea.
"Seeing life as something that is, you know, fleeting, and the world being as it is now. I've turned to my family, I've turned to my friends and I've turned to love. I'm a little less interested in the work, I would say, and more interested in that."
Speaking to British Vogue, Gyllenhaal gave a rare insight about what his future could hold: Children.
"Yes, of course I do, [want kids]" he said. "I definitely do."
This article was originally published on May 13, 2020 and has been updated.
Feature image: Getty.
Love the joy of Christmas? Take our survey now to go in the running to win a $50 gift voucher.