#72, "All Too Well," Taylor Swift (2012)

150 Favorite Songs: #72, “All Too Well,” Taylor Swift (2011)

I’m not sure that any songwriter has ever written with the same intimacy as Taylor Swift did during the Red era. I’m not exactly a Swiftie—I like a lot of her music, but a lot of it also leaves me cold—but there is just no denying what she does with “All Too Well” is absolutely masterful songwriting, hitting on every single level it aspires to reach. That was true when it was a five minute lament, and it’s even more true in the ten minute howl she released in 2021, when she re-recorded and reissued Red as part of the (Taylor’s Version) series. When I write about it here, I’ll be talking about the ten minute version, but mostly everything I have to say about that one is true about the original recording, too, since it contains the same DNA, just shorter.

Let’s start with the scarf. It’s one of a number of highly specific details in the song, something that tells us that this is a story about Taylor Swift and a man (Jake Gyllenhaal, by all accounts, who must have had a pretty bad time in 2011 and 2021) she dated for a time around her twenty-first birthday. The details remain specific: the man has a sister (presumably the great Maggie Gyllenhaal), his keychain says “fuck the patriarchy” on it, he used to play tee-ball, his mom seemed to push their relationship more than he did, he tried to network with her dad when they first met, etc, etc. And there’s a school of thought around writing that those details can be alienating; Jon Brion once told Rhett Miller that his songs were too self-referential, that “no one wants to hear the actual details of your life,” and Miller wrote recently about the way that got into his head; “My songs were getting broader and broader,” he wrote. “There were fewer half-empty Empty Bottles and more general observations about ‘love’ and ‘life.’”

Swift has had success with those kinds of songs, of course. “You Belong With Me” is pretty generic, with details that could come from any teen rom-com; “Love Story” takes its imagery from a SummerStock production of Romeo and Juliet. But “All Too Well” is so hyper-specific that it becomes universal, which is a trick that writers who are ready to do their best work tend to figure out. You don’t need to find a universal image instead of the scarf you left at this shit-ass guy’s sister’s house, because everyone has done something like that, and knowing that we’re listening to something that feels like the reality of someone’s life makes us reflect on our own. Those details place us so firmly in Taylor’s worldview that even as things get more general, they don’t feel that way. When she sings, “Maybe we got lost in translation, maybe I asked for too much, or maybe this thing was a masterpiece before you tore it all up,” we are connecting with what a fuckin’ asshole Jake was to her, embracing the song as a first-person fantasy rather than looking for scraps to connect with.

And, of course, this is a song by Taylor Swift, who has done a very good job of making sure we know the details of her life outside of her music, too. That’s something she’s seemed to chafe against at times—The Tortured Poets Department has more than one song where she seems to blame her fans for the boundaries they expect her to place on her personal life, despite having very intentionally cultivated their interest in it—but on “All Too Well,” she really is at the height of her powers, and those things work in sync together. Listen to the way she structures the ten-minute version: Full-on specificity to start, with three runs through the verse/pre-chorus/chorus, then a bridge and the song starts to slow down. We dip into the chorus from time to time as the song seems to meander, and then she’ll show up again with another verse. The effect is a little bit like you’re sitting around a bar with Taylor Swift as she’s grousing about her ex, punctuating the lulls in the conversation with something else she just thought of: “he said if we had been closer in age, maybe that would have been fine, and that made me want to die!” she bursts out after the fourth round; you sit there and watch the end of the game on the TV for a bit, and then she drops “I was never good at telling jokes but the punchline goes, ‘I’ll get older, but your lovers stay my age,’” and the whole table cracks up. The song gets prettier and more dreamlike as it proceeds, so these outbursts really grab your attention, and they’re all well-placed. It feels very much like Taylor Swift is telling the listener her secrets. It builds off of that specificity to take full advantage of the intimacy that she, as a rarity among songwriters/celebrities, can really build with her audience, and she knows exactly what to do with it. It’s just incredible writing.

And then there are the lyrics, which I would undersell to describe as simply her finest work—if Bob Dylan had written “you kept me like a secret / but i kept you like an oath” on Blood on the Tracks, it would be the best line on Blood on the Tracks. She’s never been the best singer, but she knows how to deliver a Taylor Swift line as well as Neil Young knows how to deliver a Neil Young line: the pause when she sings “it’s supposed to be fun / turning twenty-one” is one of the more devastating moments ever recorded, as damaging in its understated way to Jake Gyllenhaal as “Hit ‘Em Up” was to Biggie or “Ether” was to Jay Z. Brutal.

There are a lot of good reasons for men in their thirties to not date twenty year-old women, but if that’s you, and the ethical concerns escape you, please consider your self-preservation instinct: “All Too Well” is the sort of opus of raw big feeling that a person can really only write when they’re very young, but which an artist at that age is desperate to find an excuse to unleash. The intimacy that is built by all of the detail in “All Too Well” is all about connecting on a feelings level, aimed—if not exclusively, then at least intentionally—at an audience that was and is built largely on young women, a good portion of whom are young enough that they haven’t yet had their hearts broken in the “All Too Well” way. Which is the other thing I really love about the song—it is the sort of statement that a person can really only make when they’re heartbroken and in their early twenties, when feelings are impossibly big and every heartbreak feels like it might kill you. If you’re young and you hear it, it’s almost aspirational; if you’re older, it is a chance to connect with that depth of feeling. I think there’s a lot of power in being that age, when the feelings are still as big as they were when you were a teenager, but a good artist has had the time to hone their talent, and can communicate those feelings skillfully. There are many great breakup songs written by people in their thirties or forties or later, because by then, you have more perspective. Heartbreak is still painful, but it no longer feels like the end of the world because you’ve had your heart broken before, and the world didn’t end then, either. On “All Too Well,” Taylor Swift hadn’t yet learned that lesson, and she wrote her best song because of it.