Jake Gyllenhaal's life in pictures

By Bryanne Salazar 12:30pm PDT, Sep 18, 2017

On Sept. 22, 2017, Jake Gyllenhaal's newest movie, "Stronger," arrives in theaters. It's the true story of one man's brave fight to live after the horrific Boston Marathon bombings of April 15, 2013, left him a double amputee. In honor of Jake's powerful new film, Wonderwall.com is revisiting some of the most memorable moments in his life through photos to see how he ended up becoming one of our favorite stars of all time. Keep reading for more…

Born on Dec. 19, 1980, as Jacob Benjamin Gyllenhaal in Los Angeles, it would seem that Jake had Hollywood in his DNA. His mom, Naomi Foner, is a long-standing director and screenwriter known for films like "Running on Empty" and "A Dangerous Woman." Jake's dad is film and television director Stephen Gyllenhaal, who's worked on series like "Numb3rs" and "The Mentalist." Of course, Jake's big sis, Maggie Gyllenhaal, needs no introduction, as she's been a fixture on the big screen since 1992. Jake was 11 when he appeared in his first film, the 1991 comedy "City Slickers" (he played Billy Crystal's son, Danny). While the part was exceedingly small, it gave us a tiny window into the start of Jake's impressive career. Interestingly, while Jake's parents were supportive of his early acting endeavors, they refused to let him star in the 1992 movie "The Mighty Ducks." Although Jake had originally been cast in the film, his parents worried that he'd miss too much school. Thus, the up-and-coming star missed his chance to be in one of the great childhood films of the decade.

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This picture of Jake Gyllenhaal at 17, when he starred in 1998's "October Sky," proves that he's been a cutie basically forever. As a young kid, movie stardom wasn't the first thing on Jake's mind. In fact, Jake once told audience members at the Toronto International Film Festival that activism was one of his earliest pursuits. Before you get misty-eyed, you should know Jake's preferred cause wasn't saving the whales or even fighting against human trafficking; rather, it was to petition Kentucky Fried Chicken to bring back his favorite mini fried chicken burgers. At least the kid had spirit!

One of Jake Gyllenhaal's most recognizable early films is 2001's "Donnie Darko," in which he played the titular troubled teen who's haunted by freaky visions that encourage him to commit horrific crimes. The movie was a stark departure from his earlier roles, which, by and large, were directed by his father, Stephen Gyllenhaal. Jake shared that as a young actor, he was drawn to the darker, more deranged storylines because they felt more authentic than the typically teeny-bopper roles offered to him. "Donnie" set Jake apart from the pack and pushed him on a course for richer, more varied film work than many of his peers. The same year, Jake's next movie, the coming-of-age comedy "Bubble Boy," also premiered. Fun fact: Jake's sister, Maggie Gyllenhaal, also stars in "Donnie Darko" as his sister!

In 2002 Jake Gyllenhaal was romantically linked to actress Natalie Portman (seen here together at a charity event the same year), and again in 2006, but the pair never confirmed (or denied) they were an item. Natalie was just one of many A-list celebrities Jake has been linked to over the years.

Jake Gyllenhaal comes from a tight-knit family (seen here in 2003) that practiced both Christianity and Judaism. His parents made sure he understood the concept of charitable giving from an early age. In fact, when it came time for young Jake to celebrate his 13th birthday with a traditional bar mitzvah, his parents encouraged him to hold it at a local homeless shelter, where he served families in need a hot meal. This way, Jake could see firsthand how his privilege had allowed him more opportunities than most and give him a solid foundation for kindness to build on. (Jake later told Howard Stern that he also got a cool party — which is parenting balance at its finest.)

One of the first women to steal Jake Gyllenhaal's heart was former child star Kirsten Dunst. The two were reportedly introduced by Jake's sister, Maggie Gyllenhaal, and instantly hit it off. Their relationship lasted from 2002 to 2004 and included them buying a $1.7 million home in Los Angeles as well as adopting a German shepherd mix puppy named Atticus. When the couple split, Jake, a huge dog lover, kept Atticus.

Once upon a time back in 2001, Jake Gyllenhaal auditioned for the role of Frodo Baggins in "Lord of the Rings." As Jake explained to Jimmy Fallon, he showed up for the reading without a script and attempted to win the part, but failed miserably, especially when he neglected to use an accent. During his audition, director Peter Jackson shook his head in disbelief before later telling Jake he was "the worst actor" he'd ever seen. As we all know, the role eventually went to Elijah Wood, but because Jake's a total professional, he didn't let the loss make things weird between him and Elijah. As proof, here's a pic of them hanging out at the 2005 Independent Spirit Awards, where Jake was rocking a shaved head for the military biopic "Jarhead" — a role that earned him critical acclaim.

Although Jake Gyllenhaal has been in many movies including "Prisoners," "Jarhead," "Source Code" and "Love and Other Drugs," the film he's perhaps best known for is Ang Lee's 2005 drama "Brokeback Mountain" — a love story of two cowboys torn by their affection for one another in a time when homosexuality was considered taboo. The film garnered Jake and co-star Heath Ledger, who became close friends, Oscar nominations.

In 2008, actor Heath Ledger died from an accidental overdose, leaving fans, friends and family members devastated. Jake Gyllenhaal, who had grown close to Heath after working together on the film "Brokeback Mountain," said that the loss of his friend affected him in ways he couldn't articulate. In 2015, Jake (seen here with Heath at the 2006 SAG Awards) told reporters in Venice, where he was promoting his movie "Everest," that he missed Heath "very badly" and the loss of his dear friend made him look at his own life differently. "Knowing that life is fragile makes you want to appreciate meaningful things and stop wasting time on things that are trivial and superficial. It made me want to be more present in everyday life and be as much in the moment as I can be. It's made me see life as being much more precious than I was ever consciously aware of before and that has made a big difference with me," he shared.

While Jake Gyllenhaal's too humble to brag, it should be noted that he has been nominated for (and won) a whole lot of awards. In 2002, Jake won the Young Hollywood Award for breakthrough performance and the Chlotrudis Award for best actor. That same year, Jake appeared in his first theater production with Kenneth Lonergan's "This is Our Youth" on the London stage and ended up winning the 2002 London Evening Standard Theatre Award for outstanding newcomer for his performance. In this photo, Jake is seen accepting his 2006 MTV Movie Award for best kiss with actor Heath Ledger (they won for their work in 2005's "Brokeback Mountain").

It's expected that famous people like Jake Gyllenhaal will have equally famous friends, but the connections go far deeper for this talented star. It turns out that actress Jamie Lee Curtis isn't just Jake's buddy, but also his godmother (they're seen together here in 2006). His former godfather was none other than legendary actor Paul Newman, who passed away in 2008. Jake considered Paul to be one of his closest mentors and trusted confidants. In 2012, Jake shared at a benefit in Paul's honor that he "loved" the former star, calling him "one of the greatest actors of all time."

Another one of Jake Gyllenhaal's celebrity romances was with actress Reese Witherspoon from 2007 to 2009. The couple (seen here at a Lakers game in 2009) hooked up on the heels of Reese's split from first husband Ryan Phillippe — and at a time when she was still learning about herself as a single woman and mother of two. Jake reportedly moved into Reese's Los Angeles home in 2008, but sadly, they parted ways the following year. Jake once revealed to Howard Stern that he'd been in love three times (he later changed it to two) in his life. We're guessing Reese was included in that number.

Did you know that Jake Gyllenhaal was once cast to be Spider-Man in "Spider-Man 2" in 2004? Although Tobey Maguire originally had the role, while filming "Seabiscuit," he hurt his back and couldn't film the sequel. Jake was all set to wear the tight suit, but at the last minute, Tobey recovered and reclaimed the role. While Jake might have been bummed, the two clearly had no hard feelings and later starred together in the 2009 family war drama "Brothers" (seen here).

It's pretty clear that Jake Gyllenhaal does not want to talk about his failed 2010 relationship with songbird Taylor Swift. However, their romance — which included a whole lot of coffee dates and even a Thanksgiving visit to sister Maggie Gyllenhaal's house (Us Weekly put photos of the pair strolling through her Brooklyn neighborhood on its cover that December) — was one of the most talked-about celebrity hookups of the year. They only lasted three months, but rumor has it that Taylor's fierce breakup song "We Are Never Ever Getting Back Together" was inspired by Jake.

In 2010 Jake Gyllenhaal starred in "Prince of Persia: Sands of Time," which caused some unpleasant controversy. While fans couldn't get enough of Jake's beefed-up physical transformation and long hair, critics questioned why a white actor was chosen for a role about a man from the Middle East. While some accused the film of "whitewashing," it still performed well at the box office, raking in over $336 million.

Jake Gyllenhaal's enduring friendship with Michelle Williams is proof that in the rubble, flowers will still grow. Before Heath Ledger's death, he and Michelle named Jake as godfather to their daughter, Matilda Ledger. It was a duty Jake took to heart and since Heath's passing, he's maintained his commitment to being a father figure to Matilda while also remaining a loyal friend to Michelle (seen together here in 2014).

While Jake Gyllenhaal is no stranger to the stage, it wasn't until 2015 that he made his Broadway debut. Starring alongside Ruth Wilson in Nick Payne's "Constellations," Jake earned glowing reviews from theater critics who called his performance "astonishing" and said it was filled with "warmth, humor and vitality." The New York Times branded the pair's performance as "sexy, so accessible" and "emotionally devastating." Not bad for Jake's first time on Broadway. In February 2017, Jake returned to the stage once more with the revival of "Sunday in the Park with George" co-starring Annaleigh Ashford.

While Jake Gyllenhaal may be private when it comes to his love life, he's incredibly open about his love of dogs, including his German shepherd, Atticus, named after Atticus Finch from the book "To Kill a Mockingbird" (seen here walking with Jake in 2015). Jake has openly gushed about his pups (which also include his puggle, Boo Radley), telling Ellen DeGeneres they are "a joy to have around."

In 2015, Jake Gyllenhaal proved no role was too physically demanding to take on when he got shredded for the movie "Southpaw." The actor followed a strict diet and exercise regimen to get him in top shape to portray world champion boxer Billy Hope. While preparing for the film, Jake reportedly worked out twice a day every single day, often puking while in the gym. The film's director, Antoine Fuqua, shared that he personally witnessed Jake taking punches in the gut and ribs until he dropped. Talk about getting into character!

Jake Gyllenhaal had a busy 2017. In March, his sci-fi thriller "Life" — about a team of scientists who discover a terrifying life form that could mean the end of life on Earth — debuted to mixed reviews. Just three months later, his action-adventure film "Okja," the heartwarming tale of a young girl fighting to save the life of her mystical animal friend, arrived in theaters and on Netflix to critical acclaim. What's most interesting is how varied Jake's roles were in each of the films, even though both characters were technically scientists. In "Life" (seen here), he played a self-sacrificing recluse and in "Okja," a larger-than-life personality with a keen interest in the hippopotamus-inspired focus of the film. All it proves is that Jake clearly has amazing acting range.

Jake Gyllenhaal's final 2017 film, "Stronger," arrives in theaters on Sept. 22 and is already generating huge buzz. In the movie, Jake plays Jeff Bauman, a young man who loses his legs in the Boston marathon bombing of 2013. Co-starring Tatiana Maslany from "Orphan Black," the intense, emotional drama promises to be both painful and life-affirming. Critics have called Jake's role "riveting" as well as "triumphant" and some claim the film may land him his next Oscar nomination. Always busy, Jake's already filming his next role in the 2018 movie "The Sisters Brothers" co-starring Joaquin Phoenix.