The Countdown

Taylor Swift’s 10 greatest breakup songs, ranked

On the eve of Swift’s 11th studio album, Roisin O’Connor delves into the pop mastermind’s knack for writing breakup songs – and ranks the most devastating of the bunch

Thursday 18 April 2024 10:10 BST
Taylor Swift releases ‘The Tortured Poets Department’ on 19 April
Taylor Swift releases ‘The Tortured Poets Department’ on 19 April (Getty)

Taylor Swift knows how to write about breakups. Her candid, confessional songwriting style has traversed love in all its forms, but among her most adored songs are the ones that delve into the confusion, grief and loss that swirl around a relationship’s end. Others, while still addressing a romantic split, are about acceptance, and the ability to reflect on the past while still pushing forwards.

Her forthcoming album, The Tortured Poets Department, seems destined to serve as the apotheosis of this talent. The record follows the end of Swift’s six-year relationship with actor Joe Alwyn, widely believed to be the subject of songs about happier times on her 2019 record, Lover (“Cruel Summer”, “Lover”, “I Think He Knows”), 2020’s Folklore (“Invisible String”), and 2023’s Midnights (“Karma”).

Glance at its tracklist, and the record looks set to cover Swift’s own notes on heartbreak, with a number of song titles – such as “So Long, London” and “I Can Fix Him (No Really I Can)” – apparently referring to past relationships. Ahead of the album’s release, here are Swift’s greatest heartbreak songs to date.

10) ‘Now That We Don’t Talk’

A wildcard entry, this song is one of the best to emerge from Swift’s “Vault” of previously unreleased tracks. It features on her re-recorded version of 1989, and pulsates with that same anthemic, Eighties-indebted build. We hear her wondering about an old flame: “I guess I’ll never know,” she murmurs, watching her ex from a distance. “I miss the old ways/ You didn’t have to change/ But I guess I don’t have a say/ Now that we don’t talk.”

Her voice hits a falsetto on the chorus with ease, supple and trilling, almost carefree as she sings: “I guess I paid the price of what I lost.” Ultimately, her curiosity is tempered by acceptance and she concedes the split was for the best.

Taylor Swift performs during her Eras tour
Taylor Swift performs during her Eras tour (REUTERS)

9) ‘Back to December’

Swift’s third studio album, Speak Now, not only heralded her first steps out of the country scene and into pop – but it also marked her transition from a wide-eyed girl dreaming of princes to a young woman finding her way.

On “Back to December”, Swift sings of her regret for the way she treated someone who was nothing but good to her. Tubular bells, stark acoustic strums and sweeping strings conjure up a desolate winter backdrop as Swift trudges through the snow. “It turns out freedom ain’t nothing but missin’ you,” she sings. Devastating stuff.

Swift performing ‘Back to December’ at the CMAs in 2010
Swift performing ‘Back to December’ at the CMAs in 2010 (Getty Images)

8) ‘All You Had to Do Was Stay’

Heartbreak comes in many forms, and in this case, Swift serves it up as irresistibly catchy pop à la Robyn’s “Dancing on My Own”. The painfully underrated “All You Had to Do Was Stay” from 1989 is near-frantic with exasperation, as she chastises her ex for letting her slip through his fingers: “The more I think about it now, the less I know/ All I know is that you drove us off the road.” Then, there’s the contempt she injects into the line: “People like you always want back the love they pushed aside/ But people like me are gone forever when you say goodbye.” Ouch.

That falsetto “stay” of the song, Swift revealed, came to her in a dream in which her ex came to her door and all she could say in response was exactly that.

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“It was almost operatic,” Swift told Time in 2014. “I woke up from the dream saying the weird part into my phone, figuring I had to include it in something because it was just too strange not to.”

Copies of ‘1989 (Taylor’s Version)’ on display in record stores
Copies of ‘1989 (Taylor’s Version)’ on display in record stores (Getty Images)

7) ‘Dear John’

It’s no coincidence that many of these songs happen to be the fifth track on their respective albums. Swifties began noticing that track five on any give record would typically be the saddest. Swift acknowledged this herself in an Instagram Live before releasing “The Archer”, the fifth song from her 2019 album Lover. “Instinctively I was kind of putting a very vulnerable, personal, honest emotional song as track five,” she said.

Track five on Speak Now is “Dear John”, widely rumoured to be about Swift’s ex John Mayer, whom she dated when she was 19 and he was 32. In a masterstroke, both the opening guitar tones and the harmonising on the song are strongly redolent of Mayer’s signature sound (he somewhat bitterly dismissed it as “cheap songwriting” in a 2012 interview).

On it, Swift tackles the complicated feelings she experienced in her late teens while dating someone much older: “Dear John, I see it all now that you’re gone/ Don’t you think I was too young to be messed with?/ The girl in the dress, cried the whole way home.”

Cover art for ‘Speak Now (Taylor’s Version)’
Cover art for ‘Speak Now (Taylor’s Version)’ (AP)

6) ‘My Tears Ricochet’

Yet another track five makes the cut here – and this one is a testament to Swift’s world-building prowess. On “My Tears Ricochet”, she treads the shallows of a grey sea, haunted by ghostly siren echoes: “I didn’t have it in myself to go with grace,” she whisper-sings, as if doubled over in pain. “And so the battleships will sink beneath the waves/ You had to kill me, but it killed you just the same.”

She wrote the first lyrics after watching Marriage Story, the Oscar-nominated film about a couple going through divorce, and the result is one of her most devastating laments – depicting the shuddering aftermath of a battle from which no one emerges unscathed.

5) ‘Miss Americana and The Heartbreak Prince’

‘The damsels are depressed’: Swift’s ‘Miss Americana and the Heartbreak Prince’ is a protest anthem for the US
‘The damsels are depressed’: Swift’s ‘Miss Americana and the Heartbreak Prince’ is a protest anthem for the US (Getty Images for TAS Rights Mana)

A different kind of heartbreak: “Miss Americana and The Heartbreak Prince” shows Swift mourning a loss of innocence in the wake of the 2016 presidential election. There’s a magnificent and instinctive drawing together of her own “downfall” that same year, as she helplessly surveys the smouldering remains of her kingdom.

But this is a protest song, and one that cleverly adapts Swift’s teenage themes of prom, ballgowns and school hallways for an analogy about the country’s politics: “American glory faded before me/ Now I’m feeling hopeless, ripped up my prom dress/ Running through rose thorns, I saw the scoreboard/ And ran for my life,” she sings. But from heartbreak comes resilience, and Swift sneaks in a cheerleader’s chant even as she sounds defeated: “And I don’t want you to GO / I don’t really wanna FIGHT / ‘Cause nobody’s gonna WIN.”

4) ‘We Are Never Ever Getting Back Together’

Taylor Swift in the music video for ‘We Are Never Ever Getting Back Together'
Taylor Swift in the music video for ‘We Are Never Ever Getting Back Together' (YouTube)

To many critics, the lead single from Red was a step back from the matured songwriting of Speak Now, but the song signalled a move into the self-effacing, tongue-in-cheek style that would earn her plaudits on 1989. It was also her first single to top the US Billboard chart, heralding what would become a years-long era of Swift’s chart domination.

It is easy to see why: the track features some of Swift’s best hooks. The lyrics (perfectly syncopated) drip with sarcasm: “I’m really gonna miss you picking fights/ And me falling for it, screaming that I’m right/ And you would hide away and find your peace of mind/ With some indie record that’s much cooler than mine.” Maybe it’s more break-up than heartbreak, but Swift encapsulates the rage and indignation over an annoying ex like no one else.

3) ‘Getaway Car’

On Reputation, Swift embraced the public’s painting of her as the villain. From the venomous vite of “Look What You Made Me Do” to the villainous glee on “I Did Something Bad”, the singer revelled in her newfound status as America’s Most Hated.

That went for romance, too. On “Getaway Car”, Swift takes the money and runs, leaving her disorientated lover behind in the dust. Longtime collaborator/co-conspirator Jack Antonoff crafts a cinematic, Eighties-style soundscape redolent of Bonnie Tyler or Cyndi Lauper.

‘I was screaming “go, go go”’ - Swift on ‘Getaway Car’
‘I was screaming “go, go go”’ - Swift on ‘Getaway Car’ (2018 Invision)

2) ‘All Too Well’

One of the greatest songs of Swift’s career gained new significance when she released a 10-minute version on her re-recording of Red. The new insight added further depth to a track that already perfectly demonstrated how she has mastered the art of storytelling: the slow build, the lyrical details, the way her vocal delivery grows stronger with conviction on each verse.

“You call me up again just to break me like a promise/ So casually cruel in the name of being honest,” she cries out on the track, which is heavily rumoured to be about Jake Gyllenhaall. It’s an eviscerating portrait of post-breakup torment – and wildly fun to sing along to (all 10 minutes of it).

1) ‘You’re Losing Me’

Taylor Swift in artwork for her 10th album ‘Midnights’
Taylor Swift in artwork for her 10th album ‘Midnights’ (Beth Garrabrant)

This diamond from Swift’s Vault – written during the same sessions that produced Midnights – is written from the perspective of a relationship whose flame is flickering weakly, on the verge of going out. There are lyrical references to happier times: the room they loved “because of the light” might be the same one she danced around on “Cornelia Street” – only now she sits in the dark. The faded synths are strangely redolent of the bright, celestial nods to Sufjan Stevens on Folklore’s “The 1”, but the carefree skip in her step is replaced by a dull tread.

“I sent you signals and bit my nails down to the quick/ My face was gray, but you wouldn’t admit that we were sick,” she sings.

Then comes the chorus with its thudding heartbeat, as Swift riffs on emergency room lingo: “You’re losing me.” Her lover comes running down the corridor, but it’s too late.

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