‘All’s Well That Ends Well’ For Taylor Swift: Her Short Film Is Oscar Eligible

Swift is partnering with "a top consulting" firm for her "All Too Well" Oscars campaign. Take that, Jake Gyllenhaal.

‘All’s Well That Ends Well’ For Taylor Swift: Her Short Film Is Oscar Eligible
Photo:Dimitrios Kambouris (Getty Images)

There are very few things that I would interrupt a night of drinking for, but on Friday, November 12, my best friend and I ditched our pitchers of beer and ducked into the bathroom of a midwestern dive bar to watch Taylor Swift’s newly released All Too Well: The Short Film. We weren’t at the midnight premiere in New York City at the AMC Lincoln Square 13, but we treated it with the same reverence as if we were, heads almost touching as we hunched over my cracked phone screen, tiny versions of Sadie Sink and Dylan O’Brien flashing before us, more than ready to get our feelings hurt. We had vowed the day before to watch the short film for the first time together, not wanting to experience the magic alone. And our devotion to the video may be rewarded during awards season: The Hollywood Reporter has reported that the 15-minute film qualifies for a best live action short Oscar nomination.

Short film Oscars “are often regarded as ‘minor,’” THR reported, but if she’s nominated, Swift faces some high-profile competition this year, with Kendrick Lamar’s six-minute We Cry Together also under consideration. But in true Swift fashion, she’s not half-assing this potential trophy: She’s hired a “top consulting firm to guide its awards campaign.”

As part of her re-release of Red (the album first released in 2012), Swift told fans she would be putting a 10-minute version of “All Too Well” into the universe for the first time. (Red (Taylor’s Version) was the latest in Swift’s quest to re-record her discography in order to regain ownership over her songs’ masters, after a years-long legal debacle with her former label.) And then one week before the new version was expected to drop, Swift announced that she would also be releasing a short film of “All Too Well (10 Minute Version).” Honestly, it was almost too much to handle. Almost.

Written and directed by Swift herself, the work of art stars Sink and O’Brien in what Swift described as “a film about an effervescent, curious young woman who ends up completely out of her depth.” And out of her depth the young woman is: Over the course of the video, we see Sink’s character fall in love with O’Brien’s much older character, whose gruff charm is eons away from his boyish appeal on Teen Wolf. The lovers’ autumn car rides, late-night kitchen slow dancing, and forest make-outs come to a screeching halt when the two get into a fight about how he treats her during a dinner party. “You didn’t even look at me once!” Sink yells, a complaint that O’Brien calls “fucking selfish.”

The gaslighting screaming match ends with the pair making up without much resolution, cuing viewers into just how tumultuous the relationship actually is. In a scene preceded with a title card reading “The Breaking Point,” a muted conversation between the two show the exact moment they call it quits, followed by an almost too-difficult-to-watch scene in which Sink full-body sobs in her bed—an Oscar-winning performance indeed. It’s not all devastation for Sink’s character, though. At the end, Swift appears, playing an older version of the character who goes on to publish a book also called All Too Well, presumably about her past relationship. Life imitates art—and vice versa. Even with the song’s length, the song just refuses to drag on and is filled with dynamic key changes and gut-wrenching lyrics that didn’t appear in the 2012 version. (“Just between us did the love affair maim you too?” Unsure, but it definitely maimed us, Taylor).

Swift is notorious for drawing on her own relationships (and their inevitable demises), and “All Too Well” has long been speculated to be about her ex-boyfriend, Jake Gyllenhaal, whom she dated for three months from 2010 to 2011. At the time, Swift was 21 and Gyllenhall was 32 and, as the short film alleges, Gyllenhaal was not particularly careful with Swift’s emotions. While Swift has made it clear that she remembers that period of her life vividly, Gyllenhaal has remained relatively silent on the matter. After months of no commentary, Gyllenhaal finally said in a February interview with Esquire, “It has nothing to do with me. It’s about her relationship with her fans.” OK, sure, Jake.

As heart wrenchingly spectacular as “All Too Well” has always been—now made even more so by its accompanying film—Swift never anticipated the break-up ballad to be a fan favorite. Once referred to as a “deep cut,” it was never an album single, and Swift has confessed in the past that she thought the song would be too personal and too sad for fans to connect with. Boy, how wrong she was: In the 10 years since its release, “All Too Well” has been lauded as one of Swift’s best and “most important” songs (which is quite the feat considering how many records she’s put out). Now, the song that once brought her to tears during live performances is one she can sing with confidence, conviction, and grace, proving that holding on too tightly to your exes isn’t always a bad thing… and might even win you an Oscar nomination.

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