- [1999] Being a star doesn't last. That's not what life should be about. It's a complete illusion that really has nothing to do with you. For me, finding out about life is the most important thing.
- [on the one role that got away] I'd have to say Ewan McGregor's part in Moulin Rouge! (2001). It was so close. I sang and everything. I went through months of auditions. It was between me, Heath Ledger and Ewan. I think it came down to age and where people were in their careers. I was the youngest and the least known. I would hope it didn't have anything to do with talent. Maybe it did.
- I admire actors and artists who devote just as much time to their life as they do to their work.
- In a perfect world, I would love to do one play for every three movies.
- The truth is most of the films that make a lot of money no one remembers, and I'm not interested in making films that no one remembers.
- Coming from a family where my mom is a writer, I just respond to how people speak.
- [on the stages of fame in Hollywood] First, it's "Who is Jake Gyllenhaal?", then it's "Get me Jake Gyllenhaal", then "Get me someone who looks like Jake Gyllenhaal", and then "Who is Jake Gyllenhaal?". Right now, I'm between "Who is Jake Gyllenhaal? and "Get me Jake Gyllenhaal".
- Some movies you fall a step behind and some you stay in the same place, make the same choices. And then sometimes there are people who know more than you but show you, and that's the maximum you can hope for - doing that with someone who says, "I like you for what you are, and I want you to be in my picture." I didn't have to fake it or put on a mask - all the resources I had inside me were more than adequate. I don't want to pretend to be something ... I'm not pretending any more to fit somebody's mold. That's a long-winded statement but - why not do what you really think, even if it's a mistake?
- You know, it's flattering when there's a rumor that says I'm bisexual. It means I can play more kinds of roles. I'm open to whatever people want to call me. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened. (December 2005)
- [on filming Brokeback Mountain (2005)] I fooled around with Heath Ledger and Michelle Williams got pregnant.
- We live in a sad time where actors are politicians and politicians are actors.
- [on why he dislikes films with obvious political messages] It's very important for me to be in movies that don't have a message. Messages tend to be a little preachy, and I don't think that's what movies are about. It's important for me to be in movies that have a human level, have a heart in them. That's the reason why I did this (Rendition (2007)) and it just so happens to be really topical. This political issue is a very important one right now which, as Americans, we need to look at. So it seems like it's (the film) is very political, it seems like there's a message in it, but ultimately there's a real story about human beings dealing with actual human things.
- I think my strength is to do a take all the way through. I am definitely not someone who can do a sprint. Maybe I am not that smart, but it takes me a while to find the moment, and I like to be pushed toward it.
- When you grow up there is some compromising to do. But compromising creative instinct is never good.
- [on Love & Other Drugs (2010)] Annie (Anne Hathaway) and I already had sex on film in Brokeback Mountain (2005), so I wasn't too nervous. There's something about the way Annie and I both work which is inherently very musical. It's all about rhythm. There's a rhythm to writing, there's a rhythm to sports and there's a rhythm to sex.
- [on training for the police movie, End of Watch (2012)] We were all Tased. The whole cast. We decided that we thought it would be a sort of semi-bonding experience. When we had a choice between between pepper spray and being Tased, we were told by the professionals that Tasing was probably the preference because pepper spray lasts for a long time after. And a Tase is done in moments. Se we decided to go for quick and painful.
- My parents were relatively progressive in their spiritual beliefs: my father is Christian and my mother is Jewish. On my 13th birthday, they thought it was important for me to experience a rite of passage, an entrance into manhood, and the consensus was that we would do something for the good of the community, some charitable work - a barmitzvah-like act, without the typical trappings. So we went to a homeless shelter and we did some work there and then I had the party - the celebration - there.
- My dad descends from the Swedish Gyllenhaal family, a noble lineage that my ancestor Nils Gunnarsson Haal established in the 17th century and which has been very influential in Sweden for a long time. My great-grandfather emigrated to the USA. But I see myself as a Jew since my mother is a Russian-Jewish New Yorker.
- It's only appropriate as an indulgent actor to think about quitting 'cause it's such an intense job.
- The biggest mistake that I've made is not really admitting to myself that filmmaking is a director's medium. We all get into situations where we're working with people, and we try to control that. But I realized once I'm gone it's going to be the director's vision from here on out.
- [on his failed audition for the role of Frodo Baggins] I remember auditioning for The Lord of the Rings and going in and not being told that I needed a British accent. I really do remember Peter Jackson saying to me, "You know that you have to do this in a British accent?" We heard back it was literally one of the worst auditions.
- [on playing Donnie Darko] For me, personally, when approaching the role, it was sort of hard to figure out, because there's so many things that he gets hit with. I think that Donnie is what he comes in contact with.
- [on Louis Bloom in Nightcrawler (2014)] My grandfather (whose parents were immigrants from Russia) he really wanted me at one point to read this story about Billy the Kid, because Billy the Kid was an immigrant, essentially, and he was someone that came here to reinvent himself, and that America is made up, obviously, out of the idea of reinvention, and that Billy the Kid is this quintessential American character, and was an immigrant. He reinvented his identity to become the quintessential American. And I think that Lou is a product of the times; he's been created...
- One of the greatest performances I've ever seen is Max Pomeranc as the young boy in Searching for Bobby Fischer (1993). Something about watching a child and his ability to be honest, and his desperation for honesty, even in the midst of all the adults surrounding them, which is essentially what that movie is about, and the performance itself is so present and exists on its own even today.
- [on working with sister on Donnie Darko (2001)] It was really hard for me and my sister, I was nineteen years old and she was twenty three I would always say "what are you doing? That's acting to you?" and she would say "oh you suck" so then I would say you're such a faker" it was very "sibling-esque" but my sister is probably the reason why I do this, she's somebody I admire more than anybody in the world and drives me fucking nuts sometimes.
- [Advice for acting students] The way you behave with everybody is more important than the work you do. Generosity, kindness and patience will get you so far: that's the biggest lesson I've learned.
- [on what he is personally fearful of] Many things. I think we're living in a particularly scary time. But I'm Jewish, so I have a tendency towards anxiety. With my work, no matter how much time and preparation I've had, I'm always scared. But I know what a privilege it is to do the job that I do. I know how amazing it is to be able to choose the work that I do.
- [on receiving more attention for his abs in Prince of Persia than his character] It's fine, it's definitely flattering. I think there's a definite focus on vanity, and I think we all focus on it, which is so unimportant to me. What's interesting is the character being played.
- [on his nearsightedness] Without contact lenses, I'm practically blind. This is where the mystery of my weird view of things comes from.
- I was good at playing a smoker, all deep thinking and philosophical, and I had even bought a professional humidor that I never used. I also tried pipes for a while, but, in the end, I realised I prefer not smoking at all.
- You're tied to the facts [when it comes to movies like Everest (2015)]. But at the same time, you need to bring your own truth to the situation. I think that all of us are trying to become these people, their essence, while staying true to what we believe.
- Baltasar [Kormakur] likes to roll and wants us to experience the elements, and he pushes us in that way. I love that in making movies; getting as close as you can to the real thing is always fascinating. He's relentless, driven, courageous and a bit crazy at times. There's fearlessness to him, and at the same time, he's incredibly sensitive and understanding.
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