Taylor Swift is the only woman in history to win the Grammy Award for Album of the Year three times, tying for the most wins alongside Frank Sinatra, Stevie Wonder and Paul Simon. She’s a singer, songwriter, producer, actor, and director and – as her TIFF premiere of All Too Well: A Short Film announces to the world – a really gifted filmmaker.

The artist has long leaned on visual storytelling with music videos extending from her songs. All Too Well: The Short Film runs fourteen minutes and stars Sadie (Stranger Things) Sink and Dylan (Teen Wolf, Maze Runner) O’Brien as a couple who fall in love and eventually move from the intoxication of their relationship to fighting to a devastating breakup, all told by the lyrics but occasionally stopping for a few minutes of on-screen dialogue telling the story. When Tiff CEO, Cameron Bailey, sat down with the global pop star to discuss the film, shot on 35mm, they were accompanied by a packed house that hung on every word.

In your initial development as a songwriter coming up, how much of the process for you was visual?

It was always part of the process, because when I would write a song, I would immediately start thinking of, ‘how do I want to present this on stage?’ If I made a music video for this, what would it look like? And then when I would create an album,  partially through or halfway through, I would start conceptualizing, ‘what does this album look like? What are the colors we’re dealing with here? What are the themes? What are the aesthetics? What do I want this to symbolize?’

How much control did you have over your previous music videos?

Early on when we would make music videos, the process was, I’m 16, I’d reach out to a video director and I’d say, “Hey, I think it would be cool if the concept was that I’m in love with my best friend in high school, and he lives across the street, but there’s this cheerleader he’s dating. But there’s a football game, then the dance and there’s some science.” You come up with concepts and over time I started to take on more and more responsibility creatively and the more I took on creatively, the happier I was so here we are.

What films did you love growing up and what images from movies still stay with you as a musician?

I’ve always really loved certain films during certain phases I was in musically. I made an album called 1989 and I would watch John Hughes movies. I’d just watch 16 Candles and The Breakfast Club all the time over and over. I remember the pandemic hit and I was watching a lot of Guillermo del Toro and my whole world turned into folk tales and forests and mythical creators. Shape of Water is one of my favorite films ever and then I watched Rear Window which gave me some cinematic inspiration too.

What was the most important scene for you in this film?

I think you can tell a lot about people based on how they fight or argue, and I went into this film with a few scenes being scripted out but knowing I wanted to show one fight in depth and at length. We filmed them breaking up, we filmed them falling in love and some of the dialogue with that. But as we got closer to it, I was like, ‘It’s going to be the fight.’ We had scripted it out, but I had talked to Dylan and Sadie so much about what their intentions were and what exactly it is that’s the catalyst for this fight and I was lucky to be dealing with such emotionally intelligent actors.

Why did you decide to make a short film around one of your songs and not a music video?

I’ve always been fascinated with the dynamic of the age of the character that Sadie’s playing and what a precarious age that is when you could fit back at your family home, but you sort of don’t. You could fit in an adult’s cultivated apartment, where they have a French press and all the things that adults have, but you kind of don’t. So, you kind of fit everywhere, but you kind of fit nowhere and I think that plays into a little bit of where she’s coming from. It was a longer story to tell, and I was blown away by the way they both played it.

Are there any female directors that inspired you?

I adore Nora Ephron as a writer/ director. I love Chloe Zhao, Greta Gerwig, Lena Dunham. There are many women I admire and I’m lucky enough that Lena is a good friend and always there for me if I have a question.

Do you see yourself directing films in future?

I think I will always want to tell human stories, about human emotion. I never say never, but I can’t imagine myself filming an action sequence. If it happens one day, honestly, that’ll be funny character growth, but at this point I could see myself going in a more comedic, irreverent place.

Watch Taylor Swift’s short film here: