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Breaking down the emotional tracks — from "All Too Well" to "You’re on Your Own, Kid" — that hold the coveted track 5 slot.
Taylor Swift has always been a big fan of musical traditions: there's her ongoing fascination with the hour of 2 A.M., a long-standing habit of including talking interludes in her lead singles, the golden years of hidden messages in liner notes. But perhaps the most unwavering and constant institution in the Swift musical catalogue — which officially hit ten studio albums, following the release of this year’s Midnights — is the legendary track five, which over the years has come to be known as each album's most emotionally raw track.
For the casual listener, track five can usually be counted on to be a solid addition to any album; for the die-hard Swiftie, it's the holy grail, a look into the darkest page in Swift's notebook — and, almost always, cause for fervent obsession (Swift once even put out a whole merch collection based on the track number). "I didn’t realize I was doing this, but as I was making albums, I guess I was just kind of putting a very vulnerable, personal, honest, emotional song as track five," Swift said during an Instagram Live in summer 2019 while promoting her seventh album, Lover. “So because you noticed this, I kind of started to put the songs that were really honest, emotional, vulnerable, and personal as track five."
It's safe to say that Swift, one of this generation's best songwriters, has succeeded in this regard on all nine of her track fives — but since this is the internet, it's time to argue over which one did it the best. Ahead, a ranking of all of Taylor Swift's track five songs.
10. "Cold As You"
(Taylor Swift, 2006)
On her debut album, Swift comes out swinging on her first-ever track five, singing of frigid temperatures that still have never been "as cold as you." (Freezer) burn! Yet, when compared to her forthcoming offerings, this one doesn't quite pack the same hefty emotional punch — though, keep in mind she was 16 when this came out.
Best lyric: "And you come away with a great little story / Of a mess of a dreamer with the nerve to adore you"
9. "White Horse"
(Fearless, 2008)
Just two songs after she sings about Romeo coming to save her from feeling so alone, Swift ruminates on what happens after the fairy tale ends, when the prince and his titular steed simply can't get the job done anymore. It's a smart twist on the pop song ("Love Story") that turned her into America's sweetheart, and by releasing it on the same album, shows she had a whole lot more up her sleeve. (Plus, bonus points for having peak-Laguna Beach hot Stephen Colletti in the music video.)
Best lyric: "I was a dreamer before you went and let me down"
8. "All You Had To Do Was Stay"
(1989, 2014)
From the glittering hyper-pop album 1989, "All You Had To Do Was Stay" is a certifiable bop. It's also perhaps Swift's best f*ck you to f*ckboys, as she reprimands an ex-love for changing his mind too many times. Classic f*ckboy shit. While this is certainly danceable, it's not necessarily the most tear-jerking of the bunch which, let's be honest, is what we want from a track five at this point; "Clean" or even "Wildest Dreams" would have made more sense in the slot. The downright emo screaming of "You ended it!" pre-bridge bumps it up a few spots, though.
Best lyric: "People like you always want back / The love they pushed aside / But people like me are gone forever / When you say goodbye"
7. "tolerate it"
(evermore, 2020)
The newest offering into the track five fold is a simple concept: wanting more from someone who doesn't appreciate you back. It's arrangement is just as simple: Aaron Dessner's piano-driven melody and not much more. "I decided on track five because of the lyrics of ‘tolerate it’ and how it’s so visual, and conveys such a specific kind of hurt," Swift said before the album's release. With this particular song, she proves you don't need much to do so.
Best lyric: "If it's all in my head tell me now / Tell me I've got it wrong somehow"
6. "The Archer"
(Lover, 2019)
The most sparse of Swift's track fives is also her most haunting. While other songs from the list take aim at potential lovers or scorned enemies, "The Archer" puts the bullseye firmly on the singer herself. Wistful and regretful at the same time, Swift's voice glides over heavy reverb (courtesy of Jack Antonoff) as she laments her shortcomings — and as a songwriter, finds power in recognizing them.
Best lyric: "I never grew up / It's getting so old"
5. “You’re On Your Own, Kid” (Midnights, 2022)
Writing a song about the perils of fame can be fraught, a topic in which the listener has no way to relate. But that’s never been a problem for Taylor. On “You’re On Your Own, Kid” she dives into the feeling of isolation — and after the past few years, whom among us doesn’t know what that’s like?
Best lyric: “I hosted parties and starved my body/Like I'd be saved by a perfect kiss”
4. "my tears ricochet"
(folklore, 2020)
A good number of the sparse, storytelling-heavy songs on 2020's surprise quarantine album could quality for the track five slot ("exile" certainly comes to mind). Instead, Swift went with "my tears ricochet," a song she described as being about what happens when the person you trust most in your life stabs you in the back, i.e., a divorce — or a nasty ownership battle with a vindictive nemesis whose name rhymes with Pooter Faun. Either way, it's a solid addition to the canon, crafted around a rage-filled eulogy — and notably is the only song on folklore written solely by Swift.
Best lyric: "And if I'm dead to you, why are you at the wake?"
3. "Delicate"
(Reputation, 2017)
On Swift's most aggressive album, "Delicate" is a shockingly vulnerable contrast (until you get to the album's final track "New Years Day," that is). Like she had previously done on 1989's standout "Out Of The Woods," the songwriter perfectly captures the fragile grey area of the start of a new relationship: You like them, but do they like you? Did you say the wrong thing? Do they feel the same? Turns out there's a word for that uncertainty, even if until now it's felt unable to articulate: delicate.
Best lyric: "Do the girls back home touch you like I do?"
2. "Dear John"
(Speak Now, 2010)
Let's say it plain and simple: Taylor snapped on this one. While she'd frequently drop hints in liner notes or on talk shows alluding to who certain songs may be about, not since her breakout "Hey Stephen" did she so plainly name someone IN THE SONG TITLE. And this wasn't just someone from high school in Pennsylvania; no, the John in question here is John Mayer. (To note: Swift never confirmed Mayer was 100 percent the John in question but... come on.) "The song ‘Dear John’ is sort of like the last email you would ever send to someone that you used to be in a relationship with," she wrote on her website at the time. "Usually people write this venting last email to someone and they say everything that they want to say to that person, and then they usually don’t send it. I guess by putting this song on the album I am pushing send."
Best lyric: "But I took your matches / Before fire could catch me / So don't look now / I'm shining like fireworks / Over your sad empty town"
1. "All Too Well"
(Red, 2012)
"All Too Well" is not just the golden standard of track fives, it's the golden standard of all Taylor Swift songs. In just over five minutes, Swift details the rise and fall of a relationship in painstaking detail: the long drives upstate, the scarf left behind, the phone call that ended things. It's all hyper specific, and yet completely universal; the breakup song to end all breakup songs. Simply, it's Swift at her very best. Taylor, if you're reading this, thank you for this one. And please, please, release the ten-minute version.
Best lyric: "And you call me up again just to break me like a promise / So casually cruel in the name of being honest"
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