Ever since he first graced our screens in the dystopian drama Donnie Darko, Jake Gyllenhaal has been stealing our hearts, consistently reincarnating himself. From Brokeback Mountain to Southpaw, Gyllenhaal has never been afraid of charging headlong into new and daunting territory.

This courage to constantly challenge himself is evident in his latest film Demolition, where Gyllenhaal plays Davis Mitchell, an emotionally baron husband who experiences a personal awakening through the process of grief. The film deals with complex themes such as fear, pain and love; all part of what Gyllenhaal calls the “big mess” of the human experience and things that should be embraced. In one of his most candid interviews yet, Gyllenhaal opens up to us about how the US election has awoken the adolescent in all of us, as well as the brilliance of Donnie Darko’s dark humour. One of the things that struck me about your latest film Demolition was the guilt that your character feels. Do you agree that guilt and grief go hand in hand for your specific character? I think really it’s a story about a man who has spent his life living in the way that general society tells him he should. Following rules and not his heart, getting married at a time that people would say is the right time, getting the job that everyone thinks is the right job, and having success in the most conventional way. In that process he lost himself, and so when this tragedy happens to him, I don’t know that guilt even comes into his mind because I don’t think he has any idea what his feelings are at all. He’s actually more just numb. It’s almost as if the trauma of the situation throws him so far away from himself that he has to start doing things in the physical world in order to bring him back to himself, before he can understand what’s happened. So for the majority of the film that’s the journey. He’s fighting through the physical world in order to get to the emotional world. And at the end of the movie he gets there very suddenly, which is why I loved the script.

It’s interesting to hear you talk about numbness in relation to conformity and comfort. It seems in our culture today that people are scared of allowing themselves to feel a certain way, and your character in this movie has certainly muted his own emotions. Is that something that you think translates to society in general? I can only speak for myself and how I feel. And most of the time I’m not sure how I feel. We live in this culture where convenience is more important than connection. Convenience seems to almost be a cloak over connection. What do you mean by convenience? I mean we live in a world where our deepest relationships are with electronic devices. There’s an awareness that we must connect but it’s so easy to avoid that, and to avoid ourselves, so it becomes hard to know how we actually feel. We – or at least I am looking for escapes wherever I can find them. So in my work I provide myself a place where there is no escape, where the demand of my work, and a privilege of my work, is to be introspective, and to tell stories that give me an opportunity to journey into myself. . . and also that are entertaining of course. I don’t like to make movies that are only preaching some idea. I think Demolition is a really fun ride in a lot of ways. You find yourself emotionally confused, laughing at a movie about loss. It’s kind of saying that feelings are contradictory to what’s happening on the outside, there’s a whole unconscious world that exists. That’s why I love Jean-Marc’s style of shooting, which is totally unconventional; no lighting, no makeup, nothing like that. Just trying to find moments. Even if that moment is not about having a breakdown because of loss, but about numbness. In some of my favourite movies, a movie like Being There, you see a character in a similar state. I’m sure if that movie came out today there would be so many discussions about where on the spectrum that character was. Everyone needs to be diagnosed because it gives us comfort to say, that person’s not normal and I am. I’m sorry, I don’t mean to be preachy. But I think we feel comfortable when we put everyone into a box and when we label everything. And the fact is, at least in my limited experience, the human experience is a big mess. The wisest people I know are a wonderful mess and constantly contradict themselves. We all have joy and love in us, and we also have perversity, and darkness, and things that we are not always proud of. I try to play characters that encompass all of that.

"The human experience seems to be a big mess. The wisest people I know are a wonderful mess and constantly contradict themselves." Jake Gyllenhaal

Right, you’ve been described as, “the best weirdo in the business.” I think what people mean is that you are very vulnerable and exposed on screen, and I think that terrifies people. I just don’t want to mislead anyone about who I am, or who I want to be. I want to portray characters that actually exist in the real world. I find it scarier when you see a world that is shiny and clean and where everyone’s clothes look perfect. A lot of people say to me, “man you do things that are so dark, why can’t you just do a romantic comedy?” But I look at those films in the same way they look at the work I’m doing. To me that’s just as dark. It’s so important to have the darkness and other alienating feelings. I remember seeing Donnie Darko almost 15 years ago now, after it had just come out and remember thinking, “What just happened?” It’s important to feel that stuff, do you know what I mean? Absolutely. And also I think that movie is really funny. It’s definitely dark, but it’s even called Donnie Darko, it’s meant to be humorous. I think it’s really fun to watch and also scary at times. But I’m interested in that. I don’t subscribe to the belief that if you play characters that exist in a darker place that it somehow means there’s something wrong. I love my life. I think the world is a really beautiful place. Are you still meditating every day? I try. I am not successful all the time, but I try.

You’ve said before that “every journey starts with fear.” I know that it plays a role in some of your films like Nightcrawler, Donnie Darko, Southpaw. What are you 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. There’s also a fear of intimacy and genuine connection. When you’re old enough, and if you’ve been hurt and have hurt people, you start to walk into every situation thinking, “Shit, how do I stay aware of my own faults?” We all have expectations. I have very high expectations and that sends me to places that are probably not always the best. That’s why it was such a wonderful thing to work with Jean-Marc. He literally doesn’t have any expectations of what the project is going to be like. He creates an environment to allow whatever is happening, really actually happening, to just happen. So that was a big lesson for me. And as a result the movie has become what it was supposed to be.

"The presidential race seems to have awoken the pre-adolescent in people – this strange and angry side that is not meant for politics." Jake Gyllenhaal