Summary

• Swift’s track 5 songs are chosen for their emotional depth, vulnerability, and powerful storytelling.
• Not all track 5s are created equal – some, like “All You Had To Do Was Stay,” fall short in conveying true emotion.
• The standout track 5, “All Too Well,” remains a fan-favorite and showcases Swift’s songwriting mastery.

Whether they’re more fitting to the particular placement criteria or simply of higher quality, some of Taylor Swift‘s 11 track 5 songs across her vast musical discography are better than others. With the release of what turned out to be a double album, The Tortured Poets Department: The Anthology, Swift brought her career total albums to 11 (along with four re-recorded Taylor’s Versions). On every Taylor Swift album since her debut in 2006, the prolific artist has selected the most soul-baring song to occupy the fifth spot on the album’s tracklist.

Although it’s a completely deliberate practice now, Swift wasn’t always aware of her tendency to make her track 5s sad songs. “Track 5 is a tradition that really started with you guys,” Swift explained in an Instagram Live session one month before dropping Lover in 2019. “I didn’t realize I was doing this, but as I was making albums…instinctively I was putting a very vulnerable, personal, honest, emotional song as track 5.” Swift has continued this sad track 5 trend for 18 years, though the tradition has generated some track 5s that are definitively more soul-baring than others.

Honorable Mention:
Although “How Did It End?” is the fifth song on the second instalment of
The Tortured Poets Department
, since
The Anthology
is not considered a separate album but rather an extension of
TTPD,
it is not technically one of Swift’s “track 5″s.

11 All You Had To Do Was Stay

Albums: 1989 (2014), 1989 (Taylor’s Version) (2023)

The worst track 5 song in Taylor Swift’s discography has to be “All You Had To Do Was Stay” from her fourth studio album, 1989. On “All You Had To Do Was Stay,” Swift reminds her returning lover that if they want her back, they shouldn’t have left in the first place. It’s meant to be an anthem about standing your ground and staying strong when an ex comes crawling back but the damage is already done, but ultimately, “All You Had To Do Was Stay” is just a middle-of-the-road song that fails to leave any lasting impression.

“Clean” would have made much more sense as a track 5, but “All You Had To Do Was Stay” just doesn’t compare to the heavy hitters in its company in terms of overall quality.

It’s rare for track 5 to be one of the most forgettable songs on its respective album, but “All You Had To Do Was Stay” fails to stand out on 1989. It’s lyrically underwhelming and makes little sense as a track 5. 1989 is Swift’s most consistently upbeat and positive album that’s least defined by heartbreak, giving her slim pickings for a track 5 placement. “Clean” would have made much more sense as a track 5, but “All You Had To Do Was Stay” just doesn’t compare to the heavy hitters in its company in terms of overall quality.

10 Delicate

Album: Reputation (2017)

One of the two track 5 singles in Swift’s discography, “Delicate” sees Swift ruminating on whether her current reputation will drive a prospective lover away. The song appears on her 2017 comeback album, Reputation, which was released after her public scandal with Kim Kardashian and Kanye West left her reputation in ruins.

Even though the lyrics are anxiety-ridden and vulnerable
,
“Delicate” is sonically deceiving and does not fit the mold

of a track 5 enough to rank it any higher than second-to-last.

Like “All You Had To Do Was Stay,” “Delicate” feels too upbeat and playful to be a track 5. Even though the lyrics are anxiety-ridden and vulnerable, “Delicate” is sonically deceiving and does not fit the mold of a track 5 enough to rank it any higher than second-to-last. Swift faced a similar problem with Reputation as she did with 1989 in that Reputation was predominantly revenge anthems and smitten love songs, so there weren’t many that could work.

“Delicate” is unique in that it is the only track 5 about the beginning of a relationship in which she ponders what the future will bring, while most of Swift’s track 5s see her reflecting on a relationship after it ends or looking inwards at her own journey. Points for originality, but “Delicate” still does not feel like a proper track 5.

9 Cold As You

Album: Taylor Swift (2006)

The track 5 that unintentionally started it all, “Cold As You” from Swift’s self-titled debut album set the tone for every song with the same album placement to follow. On the inaugural track 5, Swift compares enduring her emotionally unavailable lover’s icy demeanor to the coldest place she’s ever visited. On her website, Swift described the song as capturing “that moment where you realize someone isn’t at all who you thought they were, and that you’ve been trying to make excuses for someone who doesn’t deserve them.”

“Cold As You” ranks higher than “All You Had To Do Was Stay” and “Delicate” because the lyrical content and overall tone are much more in line with what a track 5 should feel like.

Some of the best lyrics on Swift’s debut album can be found on “Cold As You,” particularly, “And you come away with a great little story/Of a mess of a dreamer with the nerve to adore you.” “Cold As You” ranks higher than “AYHTDWS” and “Delicate” because the lyrical content and overall tone are much more in line with what a track 5 should feel like. Despite being a lyrical standout on the album, the more juvenile songwriting on “Cold As You” still isn’t as refined as most of her later stuff, including the majority of her track 5s.

8 White Horse

Albums: Fearless (2008), Fearless (Taylor’s Version) (2021)

The only Grammy-winning track 5 (discounting the ten-minute version of “All Too Well,” which is track 30 on Red (Taylor’s Version)), “White Horse” was the second single off Swift’s sophomore album, Fearless. Serving as the flip side to Fearless’ optimistic, happily-ever-after track 3, “Love Story,” “White Horse” is about the fairytale illusion shattering as Swift realizes her prince charming isn’t who she thought he was. She decides she deserves better and sets off to find someone “whomight actually treat me well.”

The marginally hopeful ending keeps “White Horse” from being as earth-shattering as the best track 5s.

Just as a good track 5 should, “White Horse” spoils the fantasy that the album spent the first four songs constructing. Still, “White Horse” doesn’t quite pack the same gut punch as other track 5s to rank it any higher. It’s sad, sure, but the marginally hopeful ending keeps “White Horse” from being as earth-shattering as the best track 5s.

“White Horse” won Best Country Song and Best Female Country Vocal Performance at the 2010 Grammy Awards.

7 The Archer

Album: Lover (2019)

After steering off course on 1989 and Reputation‘s track 5s, Swift returned to form with “The Archer” on her seventh studio album Lover. “The Archer” also marked Swift’s first track 5 that wasn’t explicitly about a romantic relationship, old or new. Instead, on “The Archer,” Swift confronts and unpacks her own neurosis and looks inward at her self-sabotaging behavior and harmful tendencies.

Ultimately, “The Archer” lands below the remaining track 5s because it feels stagnant.

Though this introspective examination features some of Swift’s most creatively expressed lyrics, “The Archer” lands below the remaining track 5s because it feels stagnant. Although it picks up a bit on the pre-choruses, by never letting the beat drop, the unchanging production evokes the feeling of anxiety that she’s describing in the song. This creative choice may have served a purpose in the song itself, but it prevents “The Archer” from encompassing the full range of soul-crushing emotion present in other track 5s.

6 You’re On Your Own, Kid

Album: Midnights (2022)

Featured as track 5 on Swift’s 10th studio album, Midnights, “You’re On Your Own, Kid” chronicles Swift’s rise to fame by going right back to the beginning and tracing all the “blood, sweat, and tears” she put into pursuing her dreams. “You’re On Your Own, Kid” serves as a reflection on her coming of age, as she looks back on how far she’s come and all the pain she’d endured along the way.

“Your On Your Own, Kid” is definitely personal like a track 5 ought to be, but truthfully, there were more heartwrenching songs on the 3am Edition of Midnights that would have been better selections for track 5. Had they made the standard edition, songs like “Bigger Than the Whole Sky,” “Would’ve Could’ve Should’ve,” or even “Dear Reader” would have hit harder as track 5s.

“You’re On Your Own, Kid” doesn’t leave the listener emotionally wrecked, which is in many ways a good thing, but renders it less effective as a track 5.

Unlike most of Swift’s track 5s, “You’re On Your Own, Kid” ends on a wholly hopeful note, as Swift reassures herself that even though she’s still on her own, she’s “got no reason to be afraid” and “can face this.” It’s a sweet, comforting conclusion, but one that doesn’t fit as well in the track 5 canon. “You’re On Your Own, Kid” doesn’t leave the listener emotionally wrecked, which is in many ways a good thing, but renders it less effective as a track 5.

5 Tolerate It

Album: Evermore (2020)

A harrowing account of unreciprocated love, “tolerate it” describes an unhealthy relationship dynamic in which the younger partner is completely undervalued by the older one. The lyrics of Swift’s “tolerate it” were inspired by the bookRebecca (1938) by Daphne du Maurier about a woman who marries an older, wealthy widower and realizes she’ll never measure up to his titular dead wife, who is haunting their home.

Swift said she selected “tolerate It” as track 5 on Evermore because it “conveys such a specific kind of hurt.”

Between the emotionally devastating lyrics and unintentionally off-putting yet striking production, “tolerate it” is one of themost crushing songs in Swift’s whole catalog. Swift said she selected “tolerate it” as track 5 on Evermore because it “conveys such a specific kind of hurt.”

However, “tolerate it” loses points because of its detachment from Swift’s personal experience. Although she related to the woman from Rebecca whose husband merely “tolerates” her love, “tolerate it” is a clear departure from the pure autobiographical nature of Swift’s previous track 5s. Some of Swift’s best work on Folklore and Evermore have been fictionalized stories, but when it comes to track 5s, this narrative distance interferes.

4 So Long, London

Album: The Tortured Poets Department (2024)

The latest track 5 to join the club is “So Long, London,” featured on Swift’s 11th studio album, The Tortured Poets Department. On “So Long, London,” Swift bids farewell to the titular city and the lover she’s leaving behind in it after trying to salvage their dying relationship with no reciprocated effort for too long.

Swift’s vocal delivery on the verses compared to the bridge shows the range of her exasperation, transforming from deep, guttural, breathlessness to full-on screaming.

“So Long London” is one of the best songs on The Tortured Poets Department, which has the longest tracklist of any Swift album with 31 songs. Swift lays all her pain and frustrations bare on this heartbreaking ballad, presumed to be about Swift’s breakup with her British actor Joe Alwyn, whom she lived with in London for many years. Swift’s vocal delivery on the verses compared to the bridge shows the range of her exasperation, transforming from deep, guttural, breathlessness to full-on screaming.​​​​​​​ It may be the baby, but “So Long, London” has outdone many of Swift’s previous track 5s.

3 Dear John

Albums: Speak Now (2010), Speak Now (Taylor’s Version) (2023)

Described by Swift as “the last email you would ever send” to an ex-lover, Swift uses “Dear John” as an open letter to a much older man (widely believed to be fellow musician John Mayer) to call him out for severely mistreating and manipulating her when she was only 19 years old. At 6:45 on the re-recorded album, “Dear John” is Swift’s longest track 5 by over a minute. The slow-burn ballad takes its time building up over the first four minutes before exploding on the bridge just like the figurative “fireworks” over the titular John’s “sad empty town.”

Swift’s wise, brilliantly articulated perspective showed immense maturity in both her songwriting and as a person, while simultaneously making the point that she was “too young to be messed with.”

Before “my tears ricochet” from Folklore was released in 2020, “Dear John” was the only track 5 Swift had written entirely herself. Swift’s wise, brilliantly articulated perspective showed immense maturity in both her songwriting and as a person, while simultaneously making the point that she was “too young to be messed with.” This was her first truly great track 5 that has continued to earn its spot in the top 3.

A “Dear John” letter is a type of letter a man’s romantic partner would write to inform him that their relationship is over.

2 My Tears Ricochet

Album: Folklore (2020)

On Instagram, Swift described “my tears ricochet” as a tale of “an embittered tormentor showing up at the funeral of his fallen object of obsession.” In reality, the song is an extended metaphor for Swift’s masters dispute, which led to the destruction of her 15-year friendship and professional relationship with the founder of her former record label, Scott Borchetta. The context adds a layer of tragedy, but this ballad about a sudden, life-altering betrayal is still powerful enough in itself.

“My tears ricochet” was the first song Swift wrote for Folklore, setting the sonic and thematic tone for the rest of her Grammy-winning, career-defining eighth studio album. Ultimately, “my tears ricochet” earns the second spot on the ranking because it was practically born to be a track 5 from the beginning.

Swift acknowledged that while “picking a track 5 is sort of a pressurized decision,” she “knew from day one that [“my tears ricochet”] was probably going to be it.”

In Swift’s concert documentary, Folklore: The Long Pond Studio Sessions, on Disney+, Swift and producer and co-writer Jack Antonoff concurred that “my tears ricochet” was one of the saddest songs on the album, which earned it track 5 status. Swift acknowledged that while “picking a track 5 is sort of a pressurized decision,” she “knew from day one that [“my tears ricochet”] was probably going to be it.”

1 All Too Well

Albums: Red (2012), Red (Taylor’s Version) (2021)

Arguably Swift’s most famous and quintessential track 5, “All Too Well” was released on Swift’s fourth studio album Red, and quickly became a fan-favorite. On “All Too Well,” Swift reflects on a failed relationship that left her emotionally destroyed. She recalls specific, expository details from that time to evoke vivid imagery and paint a full picture of their relationship, including the agonizing aftermath.

“All Too Well” was already considered an unparalleled feat in storytelling for Swift and a songwriting masterpiece before the extended cut was
released
from the vault.

“All Too Well” is widely believed to be about Swift’s relationship with Jake Gyllenhaal in 2010-2011, when she was 20-21 and he was 29-30. New lyrics on the 10-minute version about a significant age gap and missing Swift’s 21st birthday further supported this claim.

Like “my tears ricochet,” “All Too Well” was the first song Swift wrote for Red and was 10 minutes long before she shortened it to five-and-a-half minutes for the album. Swift finally shared the 10-minute extended cut on Red (Taylor’s Version) in 2021, but “All Too Well” was already considered an unparalleled feat in storytelling for Swift and a songwriting masterpiece before the extended cut was released from the vault.

As far as crowning the top track 5 in Swift’s discography, “All Too Well” is a no-brainer. Not only is it the best of the eleven songs with this notable tracklist placement, “All Too Well” is considered by many to be Swift’s best work to date. Though the ten-minute version overshadowed it and took its place as Swift’s magnum opus, the original “All Too Well” remains track 5 on both versions of Red and no other song in Taylor Swift‘s discography has managed to beat it just yet, regardless of their tracklist placement.