Already have an account?
Get back to the

An Unofficial Ranking of Taylor Swift’s Emotionally Devastating Track 5 Songs

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Bob Levey/TAS23/Getty Images for TAS Rights Management

Taylor Swift’s discography is filled with confessional lyrics, but the singer is known for going especially deep on the fifth track of each of her records.

“Track five is kind of a tradition that really started with you guys because I didn’t realize I was doing this, but as I was making albums, I guess — I don’t know why — but instinctively I was just kind of putting a very vulnerable, personal, honest, emotional song as track five,” Swift explained during a July 2019 Instagram Live.

She continued: “So, because you noticed this, I kind of started to put the songs that were really honest, emotional, vulnerable, and personal as track five. So, that has definitely happened in the case of track five on this album Lover.”

Swift has continued the tradition since Lover, placing some of her most heart-wrenching songs in the notorious album slot. Us Weekly ranked all of the Grammy winner’s track fives to date.

Keep scrolling to see our rankings:

12. All You Had to Do Was Stay (1989)

Despite being a well-crafted and catchy breakup anthem, “All You Had to Do Was Stay” lacks the emotional depth of other track fives. With the exception of the lyric “All I know is that you drove us off the road,” which fans have interpreted as a nod to Swift and ex Harry Styles’ 2012 snowmobile accident, Swift favors general statements over specific details on this track. The result is a perfectly palatable tune — one of the more underrated ones from 1989 — but let’s just say we don’t need a 10-minute version of it.

Most Devastating Lyric: “You were all I wanted, but not like this.”

11. Tolerate It (Evermore)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Kevin Mazur/Getty Images for TAS Rights Management

During a December 2020 interview with Apple Music’s Zane Lowe, Swift said she got the inspiration for “Tolerate It” while reading the 1938 novel Rebecca.

“When I was reading Rebecca by Daphne Du Maurier, I was thinking, ‘Wow, her husband just tolerates her. She’s doing all these things and she’s trying so hard and she’s trying to impress him and he’s just tolerating her the whole time,’” she said.

Swift added that she related to Rebecca “because at some point in my life I felt that way” and described “Tolerate It” as a song “about trying to love someone who is ambivalent.”

Although Swift proved with “Tolerate It” that she can write soaring melodies over a rhythmic piano part in 10/8 time, the song still feels a bit clunky, and the poignant portrait of an imbalanced relationship gets lost in lyrics about polishing plates and laying “the table with the fancy s–t.”

However, the song is a standout moment during the Eras Tour with its theatrical staging. Swift sits across from an indifferent lover at a long dining table, eventually making her way across the expanse between them to make one final plea to him during the last chorus.

Most Devastating Lyric: “I made you my temple, my mural, my sky / Now I’m begging for footnotes in the story of your life.”

10. How Did It End? (The Tortured Poets Department)

Since The Tortured Poets Department is a double album — the second half, titled The Tortured Poets Department: The Anthology, was kept secret and released two hours after the initial drop — some fans have argued that “How Did It End?” is a track five.

The song nods to the rumor mill that begins churning as soon as a relationship ends, especially one that played out in the public eye. Swift compares probing curiosity that masquerades as “empathy” to a “hunger” for answers about why the romance ran its course.

The themes in “How Did It End?” — namely, how privacy is eroded by fame — have been explored by Swift before; however, the most refreshing, vulnerable moment of the song comes at the end when Swift admits that she can’t speak to how the love story fell apart because she isn’t sure herself.

Most Devastating Lyric: “I still don’t know, how did it end?”

9. Cold As You (Taylor Swift)

Even though Swift was just 16 when she cowrote her first-ever track five with Liz Rose, “Cold As You” demonstrates the razor-sharp lyricism that Swift is known for. It feels almost like a precursor to “Dear John” with its pointed lines about a love interest whose “condescending” attitude and carelessness has left openhearted Swift wondering how people can be so cold.

“Cold As You” shows real maturity — how did a 16-year-old write “You come away with a great little story of a mess of a dreamer with the nerve to adore you”?? — but still manages to be the kind of song you’d want to listen to while sitting with your head against the bus window after your middle school crush ignored you in the hallway. It’s a song about heartbreak and betrayal written before Swift had experienced much of either.

Most Devastating Lyric: “So I start a fight cause I need to feel something, and you do what you want cause I’m not what you wanted.”

8. My Tears Ricochet (Folklore)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
TAS Rights Management/Getty Images

Folklore’s track five was inspired in part by Swift’s complicated history with Scott Borchetta, who founded her first record label, Big Machine.

The duo worked together closely from 2005 until 2018, when Swift signed with Republic Records. They had a falling out when Scooter Braun bought the masters for Swift’s first six albums in 2019. Swift claimed via Tumblr at the time that “Any time Scott Borchetta has heard the words ‘Scooter Braun’ escape my lips, it was when I was either crying or trying not to.”

On “My Tears Ricochet,” Swift leans into the drama of the loss by likening it to a death, singing, “If I’m dead to you, why are you at the wake?” Compared to some of Swift’s more anthemic, universal songs, this one is highly specific to her experience, making it less relatable. However, plenty of listeners who have weathered earth-shattering betrayals may feel that Swift is singing right to them.

Most Devastating Lyric: “And I can go anywhere I want / Anywhere I want, just not home.”

7. White Horse (Fearless)

“White Horse” is the perfect first heartbreak song. That fairytale and/or Hollywood ending you grew up believing in? That’s been shattered by a dude with the “face of an angel” that “comes out just when” he needs to beg for forgiveness.

While Swift’s youthful performance of “Cold As You” sounds a bit like she doesn’t fully understand the sadness she’s singing about, “White Horse” is heartbreakingly sincere. Swift ties up the song perfectly by swapping out one lyric during the final chorus to reveal that she’s leaving the boy who let her down for bigger and better things. Bonus points for the way Swift’s voice breaks with emotion when she sings, “I’m gonna find someone someday who might actually treat me well.”

Most Devastating Lyric: “My mistake, I didn’t know to be in love you had to fight to have the upper hand.”

6. So Long, London (The Tortured Poets Department)

Years after singing about how she loves her London boy on Lover, Swift leaves the city and the relationship she associated with it behind on this TTPD ballad. The lyrics speak to the weariness that comes with fighting for a doomed relationship for too long.

“I stopped CPR, after all it’s no use / The spirit was gone, we would never come to / And I’m pissed off you let me give you all that youth for free,” Swift sings.

At first listen, it’s easy to miss all the pain contained in this track five. The vocals are strikingly subdued and detached-sounding compared to many of the other songs on this list. That’s because Swift has already weathered all the sadness and “tragedy” she could stand during this relationship. She’s tired, and she’s finally moving on.

Most Devastating Lyric: “My friends said it isn’t right to be scared every day of a love affair / Every breath feels like rarest air when you’re not sure if he wants to be there.”

5. Delicate (Reputation)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Don Arnold/TAS24/Getty Images for TAS Rights Management

No song better sums up the vulnerability simmering beneath the rage and bravado of Reputation than “Delicate.” Swift sings about finding love at her lowest point, fearing that she might be falling too fast, and then falling anyway.

In the chorus, Swift lays all her armor down and uses none of her usual wordplay or imagery. Instead she asks, simply and plainly, “Is it cool that I said all that? Is it chill that you’re in my head?” The song epitomizes the at times embarrassing second guessing that comes with the early stages of a new relationship.

“Delicate” is made richer given the context of what was going on in Swift’s life when Reputation was released, namely her feud with Kim Kardashian and Kanye West and the subsequent #TaylorSwiftIsOver social media backlash. However, its multilayered poignancy may be lost on the uninitiated listener, as half of the song’s brilliance lies in what Swift doesn’t say.

Most Devastating Lyric: “My reputation’s never been worse, so you must like me for me.”

4. The Archer (Lover)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Buda Mendes/TAS23/Getty Images for TAS Rights Management

With sparse, synth-heavy instrumentation, “The Archer” is often dismissed as one of the sleepier tracks on Lover. However, Swift was never so candid in the pre-Folklore era as she is on this song. Before she admitted to not feeling like a natural on Folklore’s “Mirrorball” or confessed that she feels like a problem who will probably be betrayed by her own future daughter-in-law on Midnights’ “Anti-Hero,” Swift shared some of her biggest insecurities within the lyrics of “The Archer.”

In the chorus, Swift sings, “Who could ever leave me darling, but who could stay?” Here we see the confidence of earlier tracks on the album like “The Man” fall away. On her best days, Swift sees the empire she’s built and the talent she’s proven. On her worst days, she sees the mess and the tragedy that comes with it. “All of my enemies started out friends,” she sings, a painful nod to some of her highly-publicized feuds and falling outs.

Lover stands in stark contrast to the era that preceded it, Reputation. Bubblegum pink replaced black, butterflies replaced snakes, and we were reminded that Swift’s body of work has always been about love stories, not vendettas. However, “The Archer” serves as a refreshing moment of doubt about that rebrand.

“Combat, I’m ready for combat / I say I don’t want that, but what if I do?” Swift sings. In other words, she’s not so sure she’s ready to call off the dogs and let bygones be bygones when the wounds aren’t fully healed.

Most Devastating Lyric: “Who could ever leave me darling, but who could stay?”

3. Dear John (Speak Now)

“Dear John” is over six and a half minutes long and every second of it packs a punch. More than a decade before Merriam-Webster named “gaslighting” its word of the year in 2022, Swift expertly described a calculated love interest who “changed the rules” to his “chess game” daily.

While the speculation that the song is inspired by John Mayer has generated a lot of conversation, it’s not the reason “Dear John” has stood the test of time. The takedown of a man who’s an expert at “keeping lines blurry” with girls who are “too young to be messed with” feels timelier than ever, and the triumphant bridge makes this track five more than a cautionary tale; it’s a reclamation of power after temporarily losing yourself in someone who doesn’t care. Far from feeling “run dry” with “tired lifeless eyes,” Swift is “shining like fireworks over your sad empty town.”

Most Devastating Lyric: “Well maybe it’s me and my blind optimism to blame / Or maybe it’s you and your sick need to give love then take it away.”

2. You’re On Your Own, Kid (Midnights)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Taylor Hill/TAS23/Getty Images for TAS Rights Management

Swift takes us through several stages of her life on this track five, from accepting that a crush will never see her as more than a friend to discovering her ability to escape through songwriting.

The song marks the first time Swift referenced disordered eating in her music after opening up about her struggles with body image in the 2020 documentary Miss Americana. After repeated mentions of “parties of better bodies,” Swift sings in the last verse, “I hosted parties and starved my body like I’d be saved by a perfect kiss.”

While “You’re On Your Own, Kid” laments the loneliness that Swift felt through much of her coming-of-age journey — and the things she sacrificed to get where she is today — the song’s final message is ultimately a hopeful one. During the final verse, “You’re on your own, kid” transforms from a bleak reality into a comforting mantra as Swift realizes that she’s always made it through whatever life throws her way.

Bonus points for the fact that this song inspired the Eras Tour friendship bracelets trend with the lyric, “So make the friendship bracelets, take the moment and taste it / You’ve got no reason to be afraid.”

Most Devastating Lyric: “I hosted parties and starved my body like I’d be saved by a perfect kiss.”

1. All Too Well (Red)

Every Emotionally Devastating Taylor Swift Track Five Song, Ranked
Ethan Miller/TAS23/Getty Images for TAS Rights Management

“All Too Well” is the seminal Swiftie text, and for good reason. The song displays Swift’s storytelling ability at its finest as she recalls drives upstate and late-night slow dances by the light of an open refrigerator. While each chorus features new memories and new lyrics, the repeated refrain “I remember it all too well” is present in all of them as Swift grapples with the burden of being able to recall every detail of an ill-fated love story.

During the “All Too Well” bridge, which is one of Swift’s finest, Swift compares herself to a “crumpled up piece of paper,” unsure of how to put the gravity of the experience into words, the very thing she does best.

Most Devastating Lyric: “And you call me up again just to break me like a promise, so casually cruel in the name of being honest / I’m a crumpled up piece of paper lying here cause I remember it all, all, all too well.”

In this article

Got a Tip form close button
Got a tip for US?
We're All Ears for Celebrity Buzz!