Who do you cast to play your condescending, manipulative, way-too-old-for-you ex-boyfriend in a short film set to a 10-minute song about your traumatic breakup? If you’re Taylor Swift, the answer is Dylan O’Brien — someone revered for being exactly the opposite in real life.
Swift briefly spoke about her decision to cast O’Brien in her All Too Well: The Short Film in Bustle‘s Wednesday (March 16) profile on the Maze Runner actor. Two albums into her re-recording process (which she started in an effort to legally own the masters of the music Scooter Braun acquired against her wishes in 2019), she rereleased her 2012 album Red last year along with a special 10-minute edition of one of her most critically-acclaimed songs, “All Too Well.”
The song is so universally beloved by her fans that the 11-time Grammy winner also wrote and directed a short film to go along with it, casting Sadie Sink and O’Brien in the starring roles. “Dylan was my first choice for the ‘All Too Well’ short film because he has that versatility I was looking for,” Swift told Bustle over email.
“I’d seen his work and heard nothing but wonderful things about him as a person,” she continued. “Ultimately I want to work with people who love what they do and come at it with enthusiasm, because that’s how I approach creating things too. He absolutely blew me away and I feel really lucky that I gained such a great friend from the experience too.”
According to the magazine, Swift’s message inviting O’Brien to star in All Too Well was “novella-length,” kicking off an exchange that apparently took the former Teen Wolf actor more than five minutes to scroll through. He agreed to the part — who fans generally take to be modeled after Jake Gyllenhaal — without hesitation, Bustle reports.
In turn, O’Brien described what it was like working with the pop star on the video shoot, which took place over two days in New York. He noted how willing she was to let him and Sink contribute ideas to the project, something that led to the standout moment of the short film: when the music stops cold and the two stars have a tense fight in the kitchen.
“For someone who’s that meticulous, she’s so trusting,” O’Brien said. “Everything was planned to be to music. But then when we played out that scene [with dialogue]. [Taylor] immediately marched over and was just like, ‘This is it. I’m going to play this in the video.’ The confidence to just identify that in the moment on set and take in what we were bringing to it [shows how] she’s so sound with relationships and her instincts.”