Taylor Swift opens up about 'moments of extreme grief' after losing masters: 'It was a very hard time'

Patrick Ryan

NEW YORK – It was rare, she was there and we'll remember it all too well

On Saturday afternoon at Tribeca Festival, Taylor Swift sat down for an in-depth discussion with filmmaker Mike Mills (“C’mon C’mon”) about her burgeoning career behind the camera, including writing and directing a 15-minute short film last fall for her ballad “All Too Well.”

Operatic in its emotions and scope, the short stars Sadie Sink (“Stranger Things”) as a young writer who gets swept up in a seemingly fairy-tale romance with a charismatic but controlling older man (Dylan O’Brien), whose “casually cruel” side reveals itself over the course of the relationship. Midway through the film, Swift cuts to a particularly gut-wrenching argument between Sink and O’Brien’s characters in a kitchen, which was almost entirely improvised and shot in one take.

“It is true that most of the time I was behind the monitor watching Sadie perform, I was physically clenching my chest,” Swift explained. “Every time I watch it, it’s actually hard for me to watch, especially when (she's) crying so hard that it’s concerning. It’s really upsetting in the best way.”

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Writer-director Taylor Swift at the New York premiere of her "All Too Well" short film last year. She screened the film again as part of this month's Tribeca Festival.

Sink and O’Brien joined Swift on stage at the Beacon Theatre for the second portion of the conversation, praising their director for the “freedom” and collaborative environment she created on set.

At one point, O’Brien earned knowing laughs from the audience when he described his character as a “narcissistic, egomaniacal child.” (The song “All Too Well,” first released in 2012, is widely believed to be about Swift’s past relationship with actor Jake Gyllenhaal.)

“All Too Well” has long been a favorite song of Swift’s devoted fans, so much so that she finally released the mythic, extended version of the track on her “Red (Taylor’s Version)” album last November. The singer has been in the process of re-recording her first six albums, after her old masters were sold twice without her knowledge.

“I’m in this situation, standing on this stage, talking about a short film I’m incredibly proud of, because I lost all of my work,” Swift said. “I was not able to own my work and I had wanted to since I can remember. It was a very hard time for me.”

But after learning to lean on the support of people who believe in her, Swift says she was able to overcome “moments of extreme grief” and get to a place that “I’m very happy with where my life is now.”

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Swift continued by reflecting on the organic success of “All Too Well,” which wasn’t promoted as a single when it was first released a decade ago, and originally included more than half a dozen additional verses. Responding to fans’ demands to hear the full song, Swift released the 10-minute version last year, which debuted at No. 1 on the Billboard Hot 100 singles chart.

“You guys just wouldn’t let it go,” Swift said, adding that “there’s so much happening in the music industry that’s so exciting. The fans have kind of subverted the label model of ‘we sit in a conference room and we pick the songs you’re going to like.’ You guys are like, ‘No, we don’t want to do that anymore.’ I find it so radical and wonderful, and I’m just trying to listen to the heartbeat of what fans want.”

As for Swift’s future directing ambitions, she teased that she would “love” to direct a full-length movie in the future.

“It would be so fantastic to write and direct a feature,” Swift said. “But I don’t see it being bigger in terms of scale – I loved making a film that was so intimate, with a crew that was relatively small and a really solid group of people that I really trusted.”

In addition to the 50-minute panel talk, Saturday's event included a screening of "All Too Well" and an acoustic performance of the song’s extended version by Swift.

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Tribeca Festival runs through June 19 with virtual and in-person events.