Muse turned Menace? A ranking of Taylor Swift’s exes by their breakup songs

Taylor Swift has built a musical empire by transforming heartbreaks into hits, but some breakups leave a nastier scar than the others. Here’s a ranking of the men behind her deeply impactful sad songs, from the least devastating to the most.

5. John Mayer-Sad, empty town resident

John Mayer has been the gracious recipient of death threats (internet users’ favourite past-time) which in this case was prompted by the story Taylor Swift told listeners about their eyebrow raising age-gap relationship through her song writing.

Although Swift and Mayer have exercised their right to remain silent about a relationship, the Karma singer’s pointed, raw and gut-wrenching lyrics will definitely have you doing a double take at the nature of their 2009 dynamic.

Lyrical Analysis

The regret, disgust and persistent trauma of a complex relationship when you are freshly legal is undoubtedly sharper in Would've, Could've, Should've, but that doesn’t mean Swift didn’t give insights into the manipulative ways of the promising grown man soon after she parted ways with him.

A mature Swift reflects on her teenage self on Midnights with lyrics like “And I damn sure never would've danced with the devil /At nineteen,” which was the age she could be seen singing duets with a 32-year-old Mayer onstage.She also scathingly reflects on their star-studded nature by asking Mayer “If clarity's in death, then why won't this die? / Years of tearing down our banners, you and I.”

Swift admits she’s still coping with whatever went down between them and wants him erased from her narrative, however, even her younger self felt Mayer was more sinister than he seemed.

In her 2010 track, boldly named Dear John, Swift writes, “Dear John, I see it all now, it was wrong /Don't you think nineteen's too young /To be played by your dark, twisted games when I loved you so?” among other distressing hints. “And I'll look back and regret how I ignored when they said / ‘Run as fast as you can,’” she sang at the time, a lyric she mirrors in her more biting, sharp and clenched admission of the regret she feels years after.

Ranking

Mayer ranks low on this list- not because Swift’s heartbreak isn’t devastatingly raw, but because Swift is painting a gloomier picture of psychologically abusive relationship rather than your average breakup.

4. Jake Gyllenhaal-Scarf thief

The man that inspired Swift’s 10-minute magnum opus comes second to last? Stick with me and hear me out before you crucify me anyway. Swift sings the track with lingering passion, resentment and some residual hurt about the man that made an age-gap their biggest issue.

Its no secret that their three month relationship clearly left a mark that time cannot erase for her or her fans, because it was fiery and passionate red. So, it’s difficult, and honestly somewhat subjective to place Swift’s 10-minute masterpiece this low, but in actuality, it’s a highly personalised letter to Gyllenhaal, telling him to never forget the details and nuances of their sad, beautiful tragic love affair.

Lyrical Analysis

Swift sings, “And you were tossing me the car keys, "Fuck the patriarchy" /Keychain on the ground, we were always skippin' town” which, as did her songs about Mayer, make the listener feel somewhat excluded with their specificity. However, the song also has lines such as “And there we are again when nobody had to know / You kept me like a secret, but I kept you like an oath,” that pack a punch for anyone listening.

Swift also writes, “And you call me up again just to break me like a promise /So casually cruel in the name of bein' honest /I'm a crumpled-up piece of paper lyin' here,” because she remembers their love affair all too well, making it one of the most painful and memorable lines in the extended version.

Meanwhile, the lesser famed track Sad, Beautiful Tragic, about Gyllenhaal also has similar themes to the behemoth that is All Too Well, but in a sadder, broody manner. In a soft tone, the Red singer croons, “We both wake/ In lonely beds/ In different cities/ And time/ Is taking its sweet time erasing you.” The track reminisces on a relationship that was doomed, sad and achingly beautiful.

Ranking

All in all, Gylenhaal is undeniably cemented in the glowing track that separates itself from the rest of Swift’s discography. All Too Well is much loved and admired by the singer and her fan base and often lauded as the best breakup song but upon taking a closer look, Swift seems to have had more heartbreaking experiences elsewhere.

If the songwriting genius had written a 10-minute song about her later relationships, it certainly would have passed All Too Well in terms of hurt, which is precisely why it ranks lower, Moreover, the track has taken a life of its own, and become something Swift and her fans bond over, rather than sit and cry to.

3. Joe Jonas- Mr. Perfectly fine

This Jonas brother may have been blasted by Swift for ending their relationship over the phone with a 25-second phone call in a deliciously petty pop culture moment, but Last Kiss will make you see the far less glamourised impact it had on the beloved songwriter.

The three-month relationship of two prominent, rising stars and its crazy fallout sparked a media frenzy, but a young Swift was also moved to write some of her most poignant, sad songs as of yet, with Last Kiss and You All Over Me.

Lyrical Analysis

The thirteenth track on Speak Now is gut-wrenching and its simple, yet vivid lyricism paired with Swift’s shaky voice quite literally, hits different. Swift candidly sings for the bridge, “So I'll watch your life in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe,” giving life to emotions that heartbroken listeners would know all too well.

Last Kiss ends with Swift’s inability to come to terms with the breakup after all the beautiful memories she sings about, so she tells Jonas that his name will be forever on her lips.

Another underrated country song about this duo comes from the vault, You All Over Me, which explores the lingering impact of a breakup. Swift tells Jonas that she has lived, learned, had him, gotten burned, “But no amount of freedom gets you clean / I've still got you all over me.” The short and sweet track restates how she felt during Last Kiss, but in a more reflective manner.

Ranking

Last Kiss is sure to put anyone in a somber and melancholic mood, which is precisely why it ranks so high on this list. Swift’s underrated gem deserves more appreciation for all of its elements, from the 27-second intro instrumentals to the unresolved ending, making you realise that her relationship with Jonas had unearthed her ability to write masterpieces.

2. Matty Healy- Situationship final boss

Healy, who marks a start contrast to Alwyn by constantly talking about Swift for a decade since she first looked his way, appears to have inspired some of her most rib-crushing, underrated tracks. The 1975 front man and Swift spent a while swirling into each other’s narratives and spiraling out of it, unbeknownst to listeners. Thus, he became the muse for tracks that are full of longing, desire and an end that left her with no choice but to observe from afar.

Lyrical analysis

In her album, The Tortured Poets Department, Swift references Healy in Chloe Or Sam or Sophia or Marcus and also in the Cardigan sequel, Peter.

She sings in the former, “If you want to break my cold, cold heart / Just say, 'I loved you the way that you were',” which is single-handedly one of the most pointed, crushing blows she has ever come up with.

Similar to this mood-ruiner of a song which leaves one with the sinking feeling of a breakup with someone who is their personality’s counterpart, Swift reaches out to the self-proclaimed Peter Pan after the infamous (might I add, insane) moment during her performance of Cardigan one night during The Eras Tour.

Swift re-visits “Peter losing Wendy,” but with much more hindsight and detail into their fleeting romance that inevitably ended in them separating. Peter depicts the slow fade of a relationship, its hope and love until there’s nothing left to do but turn out the light.

The hard-hitting yet poetic lines read, “The goddess of timing once found us beguiling / She said she was trying, Peter, was she lying? My ribs / Get the feeling she did.”

Swift felt the impact of her crushed hopes of happiness with Healy not just in her heart or in her bones, but much more viscerally, in her ribs.

Ranking

The tracks Healy has lead a mature, literature oriented Swift to write are full of surface level meanings anyone can understand or feel just as personally as the writer did. However, they also contain deeper meanings for literature geeks to read into, such as a nod to Peter and Wendy’s anti-climactic end, or the phrase “to peter out,” meaning “to gradually diminish or come to an end.”

This is what makes the songs about Healy hold a respectable runner-up spot on this list, coming second only to the man that has devastated Swift the most.

1. Joe Alwyn-Loss of her life

Alwyn has left the most prominent impact on Swift’s music, from being the one she ran away with in a getaway car, to becoming the loss of her life. The man of few words has irreversibly stitched himself into her discography, by being a co-writer and contributor in some of her latest albums. Swift’s longest, most private-yet-public relationship appears to have wounded her the most, as she often talks about it as something she will never be able to fully let go of.

Lyrical analysis

In tracks like Loml, You’re Losing Me and The Black Dog the songwriter truly shines as she talks about a relationship that ended simply because it had run its course.

Swift notes all throughout Loml that Alwyn would always call her the love of his love, but in the end flips the script to herself, singing, “Our field of dreams, engulfed in fire / Your arson's match your somber eyes / And I'll still see it until I die / You're the loss of my life.”

Interestingly enough, Swift had already begun foreseeing the end with the guy on the screen in her most heartbreaking song, You’re Losing Me. The track is a very raw, painful and anxious description of a relationship that is close to being over. Nearly every line is something anyone can connect with, and Swift’s sentiments are not masked with allegory or deception.

For the bridge, the So, Long London singer writes, “Stop, you're losin' me / I can't find a pulse / My heart won't start anymore for you,” noting how she feels like they are over for good.”

Ranking

You’re Losing Me, and all the other songs about her relationship with Alwyn in her eleventh studio album containing some of her best lyrical, stripped-down tracks about the end of a relationship are precisely why it ranks at number one. Swift addresses her listeners, Alwyn and herself as she navigates the end of a relationship she truly valued, which is what makes the tracks irreplaceable and oh-so-melancholic. 

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