Music

How Taylor Swift’s Best Song Went From Underground Fave to 10-Minute Masterpiece

“All Too Well” has developed a cult fan base over the past nine years, and for good reason.

A blond plays a red guitar while wearing a red dress on stage.
Taylor Swift in London in 2012. Ben A. Pruchnie/Getty Images

In 2012, a 22-year-old Taylor Swift was “happy, free, confused, and lonely at the same time,” as she sang in her appropriately named, iconic hit “22.” And nearly 10 years later, a now-31-year-old Swift is revisiting those feelings, with the long-awaited rerelease of her beloved album, Red. It’s out today as the latest in her “Taylor’s Version” endeavor, which sees the artist remaking most of her albums in their entirety in response to a nasty legal battle involving her old masters. Along with a return to songs like “22,” this version of the 2012 blockbuster comes with nine bonus tracks, the most anticipated of which is a 10-minute version of the cult-classic album track “All Too Well.”

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After several albums that skirted the lines between country and pop, Red solidified that Swift can’t be constrained by any one genre. Red featured bonafide pop hits; if you were someone who even knew what a radio was in 2012, you remember the inescapable singles “22,” “We Are Never Getting Back Together,” and “I Knew You Were Trouble.” “All Too Well,” however, didn’t get the single treatment, and while many nonsingles on Red (and Taylor’s other records) have charted regardless, this track only peaked at No. 80 on the Billboard Hot 100. The song was passing the mainstream by, but at the same time, the moody moving ballad was garnering a loyal—some might say obsessive—following, and it’s continued to do so over the years since (I myself am a member).

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“All Too Well” has become so revered that when a TikTok trend went around last year, in which fans ranked their favorite Swift songs, if anyone dared to deny “All Too Well” the No. 1 spot, angry users would inevitably flood the comments, decrying it an injustice. Over the years, music critics have hailed it as “sumptuous,” “vividly detailed,” and “Swift at her most literary,” among other praises. Rolling Stone named it both the 69th best song of all time and Swift’s best track overall; NME and Uproxx ranked it first on their similar countdowns.

Nearly a decade later, “All Too Well” is finally getting the big single status it never received the first time around. Not only is Swift granting us an explicit, extended take on the song—which, having now listened to it dozens of time, I can confirm is incredibly worth the wait—she also directed an entire short film to go with it, the marquee event accompanying her version of Red. To those who do not identify as a Swiftie, though, all this clamor may sound overblown. Why should any average person care so much about this random song, let alone get hyped for a 10-minute-long take on it? What is it about this ballad that sets it apart from Swift’s other, better-known breakup songs?

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There are tons of factors: its scene-setting; its bridge, which is arguably her best; the intrigue that comes from the strong speculation (and likely truth) that it’s about her short-lived relationship with actor Jake Gyllenhaal. And real ones know and love picking apart the meaning behind the song’s infamous references to a scarf Swift left at his sister’s house—such is our love for the track.

The Gyllenhaal breakup aspect is undoubtedly what has kept fans debating the song over the years more than many of Swift’s other lovelorn tracks. Take the details of the short film accompanying the 10-minute version: Written and directed by Swift, it stars Teen Wolf actor Dylan O’Brien and Stranger Things’ Sadie Sink (who happens to be dating Swift’s boyfriend’s younger brother, Patrick Alwyn). Swifties are already analyzing what these casting details could reveal about the song itself; O’Brien’s and Sink’s ages, 30 and 19, respectively, are suspiciously similar to that of Swift and Gyllenhaal at the time of their rumored relationship—she was 21, and he himself was 30. If there’s one thing fans know about Swift after years of decoding the Easter eggs she leaves in her songs and in cryptic social media messages, it’s that nothing she does is accidental.

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Over the years, none of Swift’s exes have received the same level of scrutiny from fans (with the possible exception of the much-maligned John Mayer) as Gyllenhaal has. Take an example from 2020, eight years on from Red’s initial release: The actor posted a childhood photo of himself on Instagram sporting glasses, and Swifties were quick to spam the comments with the “All Too Well” line “You used to be a little kid with glasses in a twin-sized bed,” because they were sure that Jake was confirming that this little kid was him, as they thought. The chances seem high that Swift’s extended take on the song will give us even more lyrical glimpses into one of her shorter, more secretive relationships, something that fans who find connection with the artist’s personal life cannot wait to pore over.

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But the reason behind what makes “All Too Well” a fan favorite and modern classic is much simpler than Easter eggs and breadcrumb trails. Its greatest gift is managing to strike that hard-to-nail balance between uniquely personal and universally relatable. Regardless of if the scarf or stories of childhood tee-ball games or gestures toward Gyllenhaal are purely lyrical inventions, what matters most about this song is how much it resonates with listeners, no matter their own stories. “And I know it’s long gone and there was nothing else I could do/ And I forget about you long enough to forget why I needed to,” Swift sings, perfectly summing up the process of moving on, when the initial sting of loss has passed and what once felt earth-shattering begins to feel more like a distant memory. And as for “Time won’t fly, it’s like I’m paralyzed by it/ I’d like to be my old self again/ But I’m still trying to find it”—Taylor, you are sick and twisted for dropping that line on us, and I love you for it.

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Even 13-year-old me, whose greatest heartbreak was witnessing my class crush ask another girl to go to California Pizza Kitchen with him, was overtaken in a way that could only be described as feral every time I scream-sang, “You call me up again just to break me like a promise/ so casually cruel in the name of being honest.” And who has ever described a breakup better than this: “Maybe this thing was a masterpiece ’til you tore it all up?” No one but Taylor, that’s who.

Swift is such a masterful storyteller that listening to “All Too Well” is like going through an entire relationship, from start to finish—the sorrow, the betrayal, the inability to move on—right alongside her. We, too, feel like we were on that little town street, because, in a way we have been. As sweet as “You Belong With Me” and searing as “Blank Space” are, they don’t capture the same sense of intimacy that “All Too Well” is steeped in that makes it such a triumphant, singular success in a catalog full of them. “All Too Well” is so widely treasured because it isn’t just a song, it’s an experience; it’s a vulnerable glimpse into Swift’s angsty heartbreak that is so visceral it’s impossible not to feel it within your own heart too.

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