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All of Taylor Swift’s Famously Devastating Track 5’s, Ranked

Photo-Illustration: Vulture, Cliff Lipson/CBS via Getty Images and YouTube

2020 will go down in infamy for a lot of reasons but at least, for once, two of them have nothing to do with Taylor Swift. This marked the year where Swift chucked the rulebook and gave us not one, but two, surprise albums (not to mention a surprise concert film for the first). evermore marks her ninth studio album, and her third in just 16 months, following August 2019’s Lover and July’s folklore. Which means something very specific to Taylor Swift fans: we have gotten a third of Taylor’s mythic track fives in less than a year and a half.

Early into her career, a pattern started to emerge of track five denoting the moment on each of her albums where Taylor really, fully gets cathartic. Fans started noticing it around 2012’s Red and “All Too Well,” and Taylor acknowledged the phenomenon in one of her Instagram Lives leading up to the release of Lover, saying, “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 5. So because you noticed this, I kind of started to put the songs that were really honest, emotional, vulnerable, and personal as track five.” Sure, Taylor explores her feelings on all of her songs, that is kind of her thing, but there is a certain vulnerability that comes with a Taylor Swift track five, and there is always a heightened level of anticipation for what these songs will hold. Taylor’s songs are always deeply personal, but there is a level of emotional rawness on these tracks that her others do not touch. These are the tracks where she lays herself bare, sans armor. While other songs dance around these themes, track five has always addressed them head on.

But is one track five better than another? If they were to be ranked, how does each stand alone and as part of a set? Would the criteria be lyrical content? Vulnerability? How likely they are to make you want to call a therapist because Oh wow, I have a lot to unpack here? All of the above, and then some. Below, I’ve ranked the nine existing Taylor Swift track fives. And to complete such a daunting task, I have developed a very scientific point system by which each song will be judged and ranked based on the following four qualities:

1. Lyrics (5 points)
2. The level of vulnerability conveyed  (5 points)
3. Extent to which the song makes me want to call a therapist (5 points)
4. How much the song makes me want to grab a hairbrush and dramatically perform it into a mirror (5 points)

For a total of 20 points possible. And so, we begin…

9. “Cold As You,” Taylor Swift (2006)

Swift’s inaugural track five. “Cold As You” takes a look at a relationship that was not-so-great. Not bad. Not terrible. But taxing in its own way. It is absolutely the most country track five on the list, and Taylor’s teenage twang really shines through. The lyrics — “And when you take, you take the very best of me. So I start a fight ‘cause I need to feel somethin’, and you do what you want ‘cause I’m not what you wanted” — really got to me at age 15, but over a decade of experience later, on both the listener and Swift’s part, it definitely sticks out as the first track five. It’s missing some of the power these tracks gained as Taylor matured and her songwriting strengthened. But there is still something special about it and the mess of a dreamer who wrote it.

Lyrics: 3/5
Vulnerability: 3/5
Call Your Therapist: 1/5
Grab That Hairbrush: 4/5
Total: 11/20

8. “White Horse,” Fearless (2008)

“White Horse” is when the glass shatters and the realization hits that life might not actually be a fairytale, and you might have to save yourself. Taylor learned this lesson pretty early on, and thankfully has been generous with that wisdom in her songwriting from her earliest days. “White Horse” shouts out the track five that preceded it with the line “I was a dreamer before you and it let me down.” And that is the sentiment written all over this song: you let me down, but who’s fault was it? It is absolutely one of the most vulnerable tracks on Fearless, but she wouldn’t figure out how to carry that theme all the way through an album’s first act and beyond — not just the fifth song — until her next album, Speak Now.

Lyrics: 3/5
Vulnerability: 3/5
Call Your Therapist: 2/5
Grab That Hairbrush: 4/5
Total: 12/20

7. “All You Had to Do Was Stay,” 1989 (2014)

All he had to do was stay. But he didn’t! And so we got this incredible bop. It is definitely the most upbeat of all the track fives, but do not be fooled: “Let me remind you this was what you wanted. You ended it. You were all I wanted. But not like this.” The flavor of vulnerability in this song is staying strong when someone you really care about ends things and then comes back, but you stand your ground and turn them away. It shows Taylor’s growth from her first album to her fifth, and is reflected in the sound; it’s synthy and dancey but with screams! A great change of pace for the fans of track fives who want to dance while they cry. Oh. Just me?

Lyrics: 3/5
Vulnerability: 4/5
Call Your Therapist: 1/5
Grab That Hairbrush: 5/5
Total: 13/20

6. “Delicate,” reputation (2017)

6. “Delicate,” reputation (2017)

One, two, three let’s dance. Another track five that is more pop song than emotional ballad but boy is it a track five. Taylor is essentially standing in front of her crush screaming, “IS IT OKAY THAT I LIKE YOU?” and hoping that doesn’t ruin everything. We know now, three years later, that it did not in fact ruin everything but in that moment you really just don’t know. Relationships are just so damn delicate, you know? Is it cool that I said all that?

Lyrics: 3/5
Vulnerability: 4/5
Call Your Therapist: 2/5
Grab That Hairbrush: 5/5
Total: 14/20

5. “The Archer,” Lover (2019)

“The Archer” is basically “Anxiety Disorder: The Song” and I am equal parts surprised and not surprised that it took seven albums for Taylor to really face her neurosis head-on. “I wake in the night, I pace like a ghost. The room is on fire, invisible smoke. And all of my heroes die all alone. Help me hold onto you.” With lyrics like that, there’s no mistaking this for anything but Lover’s track five. Taylor said she explored different types of love on her seventh album, and “The Archer” really hits home on both the romantic and self-love fronts. While the two track fives before it were upbeat, this one goes back to the slower, more melodic form that Swift track fives usually take.

Lyrics: 4/5
Vulnerability: 4/5
Call Your Therapist: 5/5
Grab That Hairbrush: 2/5
Total: 15/20

TIE: 4/3. “my tears ricochet,” folklore (2020)

In the recently released Long Pond Studio Sessions — the Netflix concert film where Swift and her collaborators perform folklore for the first time Jack Antonoff says that, for him, folklore starts with “my tears ricochet,” as it was the first song she wrote for the album. He also goes on to say, “I think it’s one of the best songs you’ve written, which is I think why you crowned it as a track five.” Taylor responds saying that picking a track five is a “pressurized decision” (sorry, Taylor, you did this to yourself!), but she knew from day one this would probably be it. And oh what a track five it is. It may or may not be told from the perspective of a ghost?! … Or a superhero?! Anything is possible with a track five. This song also contains some of her most cutting lyrics ever: “And I can go anywhere I want, anywhere I want. Just not home. And you can aim for my heart, go for blood. But you would still miss me in your bones.” Chills. Every. Time.

Lyrics: 5/5
Vulnerability: 3/5
Call Your Therapist: 4/5
Grab That Hairbrush: 5/5
Total: 17/20

TIE: 4/3. “tolerate it,” evermore (2020)

The newest track five, but it really packs a familiar punch. A lingering theme throughout Taylor’s music from album to album is not being enough in love — whether due to self-doubt or being with the wrong person, it’s a recurring presence. “tolerate it” is drenched in that idea. It’s the track five for those who love more than they are loved, a terrible situation to be in. It’s so deeply a track five, there is really no other track on evermore that could fit in its place. Like … “While you were out building other worlds, where was I? Where’s that man who’d throw blankets over my barbed wire? I made you my temple, my mural, my sky. Now I’m begging for footnotes in the story of your life.” Ouch.

Lyrics: 5/5
Vulnerability: 4/5
Call Your Therapist: 6/5
Grab That Hairbrush: 2/5
Total: 17/20

2. “Dear John,” Speak Now (2010)

Oof. Okay. “Dear John.” Where do I begin with this song? It is the longest track five, at 6:43, and it is an emotional marathon. It is a “Dear John” letter to an older man that manipulated her in a relationship — who is most likely her ex John Mayer — and Taylor really lets it all out. Taylor was 20 years old when Speak Now was released, and it takes a lot of strength to release a song like this, even if it isn’t about an incredibly popular musician. But it was! Probably! And she got a lot of flack for it. In hindsight, it’s empowering. She calls out the guy in the song for e v e r y t h i n g he did. She took his matches before fire could catch her and lit fireworks with them.

Lyrics: 4/5
Vulnerability: 5/5
Call Your Therapist: 4/5
Grab That Hairbrush: 5/5
Total: 18/20

1. “All Too Well,” Red (2012)

Arguably the most famous Taylor Swift track five of them all (so far). “All Too Well” was never a single, but it absolutely should have been. Taylor has teased fans with the existence of a ten-minute version of the song for years now, and honestly, it is time for the teasing to stop. You can find the CD it’s on, Taylor. Maybe it’s right by the scarf? Lyrically, “All Too Well” is a standout track bar none. “And you call me up again just to break me like a promise, so casually cruel in the name of being honest” absolutely describes several relationships I have personally talked about in therapy, and probably would for anyone else with a pulse and a past. While the other eight songs on this list are incredible tracks, “All Too Well” remains the crowning Taylor track and the queen of track fives. “All Too Well” feels like the heart of Taylor Swift: It is unvarnished and honest, narrative and melodic, it’s angry and sad and reminiscent at the same time. And the only reason it doesn’t earn a perfect score on this rank is because calling out a much older, very famous man (allegedly) at age 20 is peak “I’m an open book” behavior and the best use of her power that cannot be topped, even by “All Too Well.”

Lyrics: 5/5
Vulnerability: 4/5
Call Your Therapist: 5/5
Grab That Hairbrush: 5/5
Total: 19/20

All of Taylor Swift’s Famously Devastating Track 5’s, Ranked