Jake Gyllenhaal is, hands down, one of the most successful actors working in Hollywood today. His success should come as no surprise to anyone, though, since he was born into a talented family of actors, producers and even writers. His incredibly thoughtful performances in classic films such as Donnie Darko, Brokeback Mountain and Jarhead have also solidified Gyllenhaal's position as one of the most talented actors working today, leaving audiences clamoring for his next movie role. While you may think you know everything about Gyllenhaal's life—who he’s dated, his Oscar nominations and even his famous family—there is so much more to learn about the Hollywood A-lister than you could ever imagine.
15 He peed on a woman’s leg as a lifeguard
Everyone remembers the classic episode of Friends where the group decide to go on weekend beach vacation trip. This vacation doesn’t end too well for Monica, though, as she is severely stung by a jellyfish when walking along the shore. Anyone familiar with that episode is aware of the measures that Joey and Chandler were forced to take to quell the pain of Monica's Jellyfish sting.
While you may think that a situation like this could only take place in the world of a comedic television series, Jake Gyllenhaal actually lived through this exact predicament in his teenage years working as a lifeguard at Martha’s Vineyard. We wonder if the person who suffered the painful sting has any idea who the man that peed on them became?
14 He was one of the top contenders to play Batman
Christopher Nolan’s Dark Knight trilogy is one of the most successful film trilogies of all time, garnering over $1 billion at the box office over the span of the three films. It’s hard to imagine anyone other than Christian Bale in the role of Batman, but it has been reported that the casting for the part almost went in an entirely different direction. Originally, Jake Gyllenhaal was up for the part, but eventually lost the role to Christian Bale. While Gyllenhaal isn’t a stranger to playing darker roles in the movies he is a part of, it would have been hard to imagine him as the man in the cape and cowl. What would Gyllenhaal’s bat-voice have sounded like? We guess we will never know.
13 He was also supposed to be Spider-Man
Jake Gyllenhaal’s superhero near misses don’t stop with The Dark Knight. In fact, Gyllenhaal was primed and ready to fill Tobey Maguire’s position as Spider-Man in Sam Raimi’s highly anticipated sequel, Spider-Man II. During negotiations for the film, Tobey Maguire, hot off the heels of the wildly successful film Seabiscuit, was holding out for more money. The actor even went so far as to send his neurosurgeon to speak with visual effects staff to inform them that a devastating back injury would keep Maguire from reprising his role of Spider-Man. Calling his bluff, Sony quickly reached out to Jake Gyllenhaal to take over the role of the web-slinger, but upon hearing the news, Maguire quickly began fighting for his role back.
12 He’s the godfather of Heath Ledger’s daughter
One of the roles that brought Jake Gyllenhaal to the top of the list of hot Hollywood actors was his work on the critically acclaimed and all-around much talked about 2005 film Brokeback Mountain. Jake and his co-star in the movie, Heath Ledger, became incredibly close during the making of the film—so much so that Ledger and his late wife Michelle Williams would ask Gyllenhaal to be the godfather of their daughter, Matilda Ledger. The tragic passing of Heath Ledger in 2008 left a giant hole in the lives of those close to him, and Gyllenhaal still openly struggles with the passing of his close friend. Gyllenhaal reportedly remains extremely close to Michelle Williams and his now 11-year-old goddaughter Matilda.
11 He was born into a film family
Creative parents, more often than not, yield creative children. This was most certainly the case for Jake Gyllenhaal. Jake is the son of director Stephen Gyllenhaal, who worked on notable films like Homegrown, Losing Isaiah and Paris Trout. Gyllenhaal’s mother, Naomi Foner, is a producer, writer and an actress, and is best known for producing the films The Electric Company and Running On Empty. The person in his family that will be most recognizable to audiences, though, is his older sister Maggie Gyllenhaal, an incredibly talented and successful actress in her own right.
The Gyllenhaal family is filled with talented actors, writers, and producers, and it should come as no surprise to anyone that growing up in the Hollywood echelon would yield such a talented brother and sister acting duo.
10 His first role was in City Slickers
Jake Gyllenhaal is known now for his roles in successful films such as Donnie Darko, Nightcrawler and Zodiac, but his first Hollywood movie role might have slipped past the eyes of even the sharpest moviegoer. This movie was City Slickers, where Gyllenhaal played the role of Billy Crystal’s son. Gyllenhaal’s most notable scene takes place in a classroom, where he is so embarrassed by his father’s occupation as an ad salesman that he tells his peers that he is actually a submarine commander. While Gyllenhaal’s screen time was minimal to say the least, it was still a great look into the promising young career of the up and coming actor. Luckily for Jake, he didn’t get the call to appear in City Slickers II.
9 He got his first driving lesson from Paul Newman
Jake Gyllenhaal’s Hollywood lineage extends well past his actress sister Maggie and his producer/writer parents. Being that his family is so well connected in the industry, it should come as no surprise to anyone that his godfather and godmother are also prominent figures in the entertainment industry, too. Gyllenhaal’s godfather is none other than actor Paul Newman. Newman has been around Gyllenhaal since he was a boy, and he even gave him his first driving lesson. There couldn’t be a much better candidate for this, as Paul Newman spent most of his early life as a race car driver. Paul Newman isn’t Jake Gyllenhaal’s only famous godparent, though. In fact, Jamie Lee Curtis of True Lies fame is his godmother. The parade of talented people circling around Gyllenhaal is seemingly never-ending.
8 He skipped his bar mitzvah to volunteer at a homeless shelter
Bar mitzvahs are usually something most Jewish boys look forward to for 13 long years. It takes a tremendous amount of practice and training to learn to read from the Torah, and it’s a huge celebration of friends, family and people from your temple. Sure, all those things are great, but you also get presents!
Jake Gyllenhaal’s celebration was anything but a party filled with presents, family and friends. In fact, Gyllenhaal spent his bar mitzvah volunteering at a homeless shelter. Gyllenhaal’s decision to volunteer at the shelter was a way for him to show appreciation for the privileged lifestyle he had experienced growing up. Though Gyllenhaal missed out on the typical party most Jewish boys celebrate at the age of 13, his experience at the homeless shelter most certainly offered a type of life experience that slips past most teenagers.
7 He and his sister were both nominated for Oscars
Jake and Maggie Gyllenhaal are two of the most prominent siblings who have both received Oscar nods working in Hollywood today. Jake was nominated for his stand-out role in the critically acclaimed film Brokeback Mountain, and Maggie Gyllenhaal was nominated for her role in Crazy Heart. Jake had some advice to give to his sister Maggie upon her nomination, too. He reportedly told her, “It’s a lot of fun, enjoy it in that spirit. If you make it too much more than that, you’ll probably go astray.” While Jake and Maggie are the most recognizable siblings working in movies these days, several other siblings who have both been nominated for Oscars consists of River and Joaquin Phoenix, Meg and Jennifer Tilly and even Julia and Eric Roberts.
6 Gyllenhaal studied Buddhism at Colombia University
One personal trait that Jake Gyllenhaal values greatly is self-reflection. This led the actor to find a class at Colombia University that would aid him in becoming better at this personal process. As it turns out, the only class that fit the bill at the famed university was a class on Buddhism. “I am a big proponent of continuous self-reflection,” Gyllenhaal said, which he followed up with, “I don’t mean to be too lofty.”
Gyllenhaal’s constant journey toward positive and abstract thinking has even influenced his acting career. He finds that being present in the moment is one of the keys to great acting, which has encouraged the actor to ignore and even mark through stage direction that would take him out of the moment in a scene.
5 He is an award-winning theater actor
We all know that Jake Gyllenhaal is an incredibly talented actor, but what you may not be aware of is that he is also an experienced theater actor. In 2002, Gyllenhaal starred in a London stage play titled "This Is Our Youth." Jake Gyllenhaal played the character of Warren, a role that has also been played by such notable names as Casey Affleck, Michael Cera and Freddie Prinze Jr. The off-Broadway play was written by Kenneth Lonergan, and is about a 19-year-old boy who steals $15,000 from his lingerie tycoon father after he is kicked out of his house. Gyllenhaal put on such a great performance in his role as Warren that he received the Evening Standard Theater Award for it.
4 His real sister played his fake sister in Donnie Darko
Donnie Darko was one of those movies that spoke to angsty teenagers of the mid 2000s unlike any film at the time did. It was dark, psychological and above all else, completely depressing. Gyllenhaal played the role of Donnie Darko, a high school kid with some serious psychological problems who was haunted by a terrifying man in a dirty rabbit suit. As you could expect, Donnie’s home life was rather difficult while dealing with these issues. Most will remember the famous dinner scene where Donnie refers to one of the teachers at his school in an exceptionally funny yet unflattering way, while his sister, played by Maggie Gyllenhaal, revels in his sardonic attitude. We can only assume that this kind of dinner conversation wasn’t completely unfamiliar to the Gyllenhaals.
3 His parents wouldn’t let him be in the Mighty Ducks
Even though Jake Gyllenhaal’s parents are part of the film industry, that doesn’t mean they would let him take every acting gig that came his way as a teen. It's probably because of their knowledge of the industry that, as Gyllenhaal revealed in an interview with Howard Stern, they made him say no when he was offered a role in the now-classic movie, The Mighty Ducks.
“I definitely remember crying on the kitchen counter,” said Gyllenhaal. “I was like, 'You guys are crazy.' My parents were like, ‘Look, you’re about to enter junior high school, you gotta get your education, that’s the most important thing. I promise you, you hate us now, but you’ll thank us later,' and I do.” The Mighty Ducks would have been Gyllenhaal’s second acting role after City Slickers.
2 He said sex scenes with Anne Hathaway were a “tough job”
For those of us who aren’t actors or actresses, the idea of a sex scene on a movie set sounds a little bit awkward. It would have some perks, though, as most Hollywood actors/actresses' appearances aren’t exactly repulsive by any stretch of the imagination. Movies with these kinds of scenes aren’t always a bed of roses for the actors involved, though. Just ask Jake Gyllenhaal, who spent a good portion of his screen with time in the movie Love and Other Drugs getting intimate with the beautiful Anne Hathaway. “It’s a tough job getting naked with Anne Hathaway.”
“It’s not awkward, it’s our job,” said Gyllenhaal. “That’s the tough life of being an actor in the movie business nowadays. It’s exhausting.” Yeah, we all feel reallllly bad for you, Jake.
1 He broke Taylor Swift’s heart
Taylor Swift is no stranger to the celebrity dating scene. She’s been romantically linked to John Mayer, Joe Jonas, Taylor Lautner, Tom Hiddleston and even—yup, you guessed it—Jake Gyllenhaal.
Even though the two dated for just a short four months, it has been reported that Taylor Swift was heartbroken when Gyllenhaal decided to pull the plug on their relationship—so much so that she even references him in her song “We Are Never Getting Back Together.” The lyrics go as such: "I'm really gonna miss you picking fights / And me falling for it screaming that I'm right / And you would hide away and find your peace of mind / With some indie record that's much cooler than mine." That one can't be fun to hear on the radio for Jake.