The stereotype about Taylor Swift‘s music is that she only writes about breakups. While that excludes some of the more adventurous songs in her catalog, the stereotype isn’t all wrong. Swift has made a name on being able to color a song with vivid feeling and vignettes. She can take the circumstances of her life and paint stunning portraits that somehow remain universal. I revisited some of these songs and ranked them by how devastating they were. While this list isn’t comprehensive, it’s still a well-rounded look at Swift’s singular talent for a breakup song.
Videos by American Songwriter
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“Bejeweled”
“Bejeweled” carries very little emotional weight. In fact, Swift seems completely emotionally detached. She’s in the revenge stage of the breakup and finding ample ways to seem superior. This is a breakup song for those who are starting to shrug off the heartache.
“Tell Me Why”
“Tell Me Why” might have come from a place of real heartache, but it’s softened by a sense of naivety. It doesn’t feel like a breakup that’s too emotionally devastating because it feels like little more than school-ground romance.
“All You Had To Do Was Stay”
Swift is in the bargaining stage of her breakup in “All You Had To Do Was Stay.” She’s not shattered, and she’s ready to ask some hard questions of her ex. “Had me in the palm of your hand / Then why’d you have to go and lock me out when I let you in,” she sings, beginning to heal.
“White Horse”
“White Horse” does feel a tad juvenile, but it’s still emotional. This feels like it was written about Swift’s first big breakup—her first brush with real, consequential heartbreak. The sad meter is ticked up just a little more here.
“Back To December”
A breakup is hard enough in general; it’s even worse when you’re wracked with regret. Swift has oodles of regret in “Back To December,” wishing she could apologize to her ex for letting him go.
“Clean”
Swift attempts to shed an old flame in “Clean.” Many of us know what it’s like to be bogged down by the memory of someone who’s no longer in our lives. Swift explains this simple idea beautifully in this up-tempo breakup song.
“Cardigan”
You’d be forgiven for not knowing that “Cardigan” is a breakup song. The subject matter is loose enough to be endlessly interpreted. But when you dig into the lyrics, you reveal a heartbreaking reality.
“You’re Not Sorry”
When we get broken up with, it’s easy to fall for any apologies—anything to soften the blow. But, Swift accepts that false promises mean nothing in “You’re Not Sorry.” Accepting that nothing will revive your relationship is a hard truth, giving this song a certain sting.
“Dear John”
“Dear John” was at one point Swift’s most heartbreaking song, and it remains emotionally taxing. Swift bares her soul in “Dear John,” throwing any emotional caution to the wind.
“Tolerate It”
Though Swift’s Evermore isn’t expressly about her real life, she sings the songs in this tracklist with enough conviction that the emotional weight is felt. “Tolerate It” is about a woman who’s been neglected by someone close to her. Though she’s had more dramatic circumstances in her songs, the quiet devastation of this song hits hard.
“So Long, London”
“I’m pissed off you let me give you all that youth for free,” is one of Swift’s most devastating lyrics. Time wasted is a common theme in music, but few people have articulated it as clearly as this.
“All Too Well (10 Minute Version)”
It doesn’t get much more devastating in Swift’s catalog than “All Too Well.” While the original version is heartbreaking enough, she added salt to the wound with the extended mix. It’s Swift at her most transparent.
(Photo by Kevin Winter/TAS23/Getty Images for TAS Rights Management)
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