It's no secret that Taylor Swift is a master songwriter, but her The Tortured Poets Department being the most recent example of her strong songwriting development.

Her Track 5 songs, however, are truly some of the best Swift has to offer, having been purposely placed in that position as a long-running tradition of hers. Swifties will recognize that the Track 5 songs are always going to be Swift's hardest hitters on any given album, mainly because of how deep and personal Swift is willing to go. She pulls no punches on these particular songs, displaying some of her very best artistry in an effort to be as vulnerable as possible with her beloved audience.

With the Track 5 songs being some of Swift's best work, it's an extremely difficult endeavor to rank them against one another. The parameters for this particular ranking are that the best of these songs achieve a healthy variation of the following factors: excellent writing, cultural impact, fan-favoritism, and production. The following 11 of Swift's Track 5 songs so far from all her studio albums are ranked according to these parameters, listed from worst to best.

11 All You Had To Do Was Stay

1989 (2014)

There truly is no "worst" when it comes to Swift's Track 5 songs, but for the sake of this ranking, there has to be a song that takes this title - and, surprisingly, it goes to Track 5 on Swift's most revered album, 1989. "All You Had to Do Was Stay" isn't a bad song by any means, but it's a deviation from Swift's typical Track 5 formula that's quite jarring. Rather than leaning into the devastation of her own lyrics, it remains faithful to 1989's upbeat pop sound, giving the illusion that this song is happier than it actually is.

It's worked for Swift since then, in tracks such as "I Can Do It With a Broken Heart," but not as a Track 5 specifically. This is because, sadly, the writing on "All You Had to Do Was Stay" falls short of what Swift is often accomplishing on these highly-acclaimed tracks. Though the message may fit, with Swift lamenting about her lover choosing to leave her rather than work things out and stay, it's lost behind constant repetition and a heavy pop beat. It fits with 1989's overall sound, but it simply cannot compete with the other Track 5 songs.

10 Cold As You

Taylor Swift (2006)

The next song on this ranking could certainly be seen as a controversial move, given how beloved it is. "Cold As You" ranks here if only because this song debuted before Swift had truly cemented her own Track 5 tradition. With this being on her debut album, it was the first time Swift tackled a Track 5, and thus she could only improve from this point forward. That's exactly what she would go on to do, getting better and better with each new Track 5, but even "Cold As You" still stands strong on its own.

"Cold As You" is beloved by Swifties, but it simply pales in comparison to her future creations.

"Cold As You" certainly set the tone for Swift's Track 5 songs, packing an emotional punch. Here, Swift sings about how the person she was once with never allowed her the proper vulnerability, icing her out time and time again. She even sings, "You never did give a damn thing, honey / But I cried, cried for you / And I know you wouldn't have told nobody if I died, died for you" - a haunting picture of what this relationship must have looked like. "Cold As You" is beloved by Swifties, but it simply pales in comparison to her future creations.

9 Fifteen

Fearless (2008)

Adhering to many of the same justifications that were provided above, "Fifteen" arrives in the next spot on this ranking. Swift was still getting her footing with both her Track 5 tradition and her songwriting in general, and as iconic as "Fifteen" on Swift's first Album of The Year Award winner truly is, it's still a far cry from what she would go on to create - which is a testament to how fantastic all these songs really are. As iconic and nostalgic as "Fifteen" is, though, its writing doesn't align with what has now become the Track 5 method.

It does, in many ways, act as a precursor to Track 5 on her next album after Fearless, but "Fifteen" is still more of a sweet and reassuring love letter to her younger self, and thus her younger fans, than anything else. Swift sings, "But I've found time can heal most anything / And you just might find who you're supposed to be / I didn't know who I was supposed to be / At fifteen," teaching an important life lesson through her own experiences. This is an important message, but the writing of her other Track 5s still manages to sur it.

8 Delicate

reputation (2017)

Swift wasn't afraid of shaking things up with the release of reputation in 2017, which functioned as her comeback to the spotlight after the hate train that had driven her out of the public eye for at least a year's time. "Delicate" is a prime example of that, and it's become an important song within the fandom, if only for the audience participation it gets at her live shows. As a song on its own, however, it's definitely a solid one - but similarly to "All You Had to Do Was Stay," it simply deviates from the Track 5 form.

On "'Delicate", Swift sings about the titular delicacy of new relationships, and how frightening it can be to open up to someone new. "Is it cool that I said all that?" Swift asks in the chorus. "Is it chill that you're in my head? / 'Cause I know that it's delicate." The music video only further elevates this theme, allowing Swift's character to truly dance like no one's watching instead of restraining herself. It's an iconic piece of her discography, but it's still not completely up to par with the standard Swift has set for her Track 5 songs.

7 Tolerate It

evermore (2020)

Now on the part of the ranking that really hurts, we have "tolerate it" from 2020's evermore, one of the most devastating songs Swift has ever written. The placement of this one alone proves how tough the competition is; this has long since been regarded as one of Swift's most gut-wrenching masterpieces, and for good reason. On "tolerate it", Swift sings about a relationship where she feels as if her partner is simply tolerating her and her love for them rather than actually reciprocating, leaving her in a one-sided romance.

It's a completely heartbreaking picture of what it's like to love someone more than they'll ever love you.

"If it's all in my head tell me now," Swift begs on the chorus. "Tell me I've got it wrong somehow." She wants to believe so badly that she's just overthinking it, but she provides evidence in other parts of the song that she's not. She even likens the pain of this to a "dagger" that she can remove. It's a completely heartbreaking picture of what it's like to love someone more than they'll ever love you, and it's only the pure artistry and impact of the other Track 5 songs that make them rank higher than this one.

6 You're On Your Own, Kid

Midnights (2022)

Up next is the most recent Grammy Award-winning Track 5 from Swift, "You're On Your Own, Kid" from 2022's Midnights. This song isn't quite a deviation from the typical Track 5 tradition for Swift, though it's certainly different from heavy-hitters like "tolerate it." What makes this particular Track 5 stand out so much is how its lyrics created its own culture; it's on this track that Swift sings "So make the friendship bracelets," the single line that led to friendship bracelets becoming a definitive symbol of Swift and her Eras Tour.

"You're On Your Own, Kid," however, earns this higher spot for much more than a lyric about friendship bracelets. It's a touching tribute to everything Swift has been through in her life, leading up to her fully making the realization that she already has everything she needs on her own to thrive - because she's the one who's been carving her own path all this time. It's relatable for anyone who's felt as if they've been fighting through life, and also just as comforting. This deep meaning, along with excellent writing and production, sets it just outside the top 5.

5 Dear John

Speak Now (2010)

Perhaps one of Swift's most scathing yet clever songs to date is "Dear John" on Speak Now. While "Cold As You" may have been the start of the Track 5 tradition for Swift, "Dear John" is what cemented it as the place on Swift's albums for peak vulnerability through songwriting. This song has only continued to build on its own legacy with Speak Now (Taylor's Version), as the rerecording of this song created an overwhelming surge of - to the point where Swift had to remind the Swifties to be kind before she played it live on her Eras Tour.

This is because "Dear John" is a brilliant play on words, as it not only riffs on the Dear John letters that would be written to soldiers, but it also directly addresses the person Swift has written this song about (presumably, of course). Swift calls him out in her songwriting for being much too old to treat someone like Swift the way he did, essentially parading her around and treating their relationship like nothing more than a game. This is what truly set the standard for Track 5s, easily making it one of Swift's very best.

4 The Archer

Lover (2019)

One of Swift's most beloved Track 5 songs is "The Archer" off Lover, a track that was so revered at the time of its release that its title was in the top trends on Twitter. "The Archer" sees Swift taking a deep look at herself when it comes to how she handles relationships, and she reflects on her push-and-pull nature of struggling to let anyone get close and ultimately self-sabotaging. It's an extremely relatable narrative, and the songwriting here is only further enhanced by the production of the track she's singing on.

"The Archer" even made it into the Lover set on The Eras Tour, although it was cut later on to make room for The Tortured Poets Department set.

As Swift's storytelling builds, with her hoping for things to be different this time around, the production also builds with her, beginning as a quiet, tense sound that grows into the thudding of an archer's heartbeat. Even more masterful is the ending, which is abrupt - painting the image of the archer ultimately releasing their arrow. In all respects, "The Archer" is a true masterpiece in this regard, acting as a prime example of Swift's masterful storytelling that's only been topped by 3 other Track 5 songs.

3 My Tears Ricochet

folklore (2020)

Preceding "tolerate it" a few months earlier in 2020 was "my tears ricochet," a Track 5 that somehow managed to be even more devastating than the former. Swift has said that many of the songs she wrote for both folklore and evermore, more so the former, were based on fictional narratives - such as the folklore love triangle - but Swifties have collectively agreed that nothing about "my tears ricochet" is fictional. It's all raw emotion and storytelling from Swift, likely linked to a very real and very heartbreaking battle she was fighting for her own music.

Swift paints the picture of a funeral, her own funeral, in what many have deciphered as a metaphor for the sale of her masters for her first six albums by her old record label - which has since led to the rerecording projects of her Taylor's Versions. This is because of one line in particular: "And when you can't sleep at night (you hear my stolen lullabies)," with the "stolen lullabies" presumably referring to her old music. This deeply personal and devastating significance behind the song easily makes it one of Swift's best, and most memorable, Track 5s.

2 So Long, London

The Tortured Poets Department (2024)

It was known before anyone had even listened to "So Long, London" that it was going to become one of Swift's best Track 5 songs yet, if only because of what its title alone promised. The Tortured Poets Department was an album that Swift said she had to write, no doubt to help herself cope with the end of her 6-year relationship - which is the subject of this particular track. Her ex was British, and the two had a home together in London, but this song title refers to him as a symbol of London rather than the city itself.

Similar to "The Archer," the production on "So Long, London" only further enhances Swift's songwriting, building in intensity the more Swift laments about wasting her youth in a relationship that she tried so hard to keep alive. Her voice in the beginning mimics church bells to both resemble English churches and maybe even to emulate the sounds heard at either a wedding or a funeral. Still, by the end, Swift still wishes him nothing but the best: "Two graves, one gun / You'll find someone." This heartbreaking yet very real story thus earns its place beneath only one other.