In the Taylor Swift world, track five of an album only means one thing – all aboard the super-highway to heartbreak and pain. Tugging on the heartstrings with stabbing lyrics and climactic bridges, Taylor Swift’s infamous track fives are consistently her most anguish-filled songs; they have achieved folklore (sorry) status among her fans. And because we love suffering, we’ve decided to rank them.
When it comes to being torn into tiny little emotional tatters, catchiness doesn’t really enter into the equation. Instead, we’ve weighed up a number of factors, including: solo sob potential, stirring instrumentals, and how intensely the lyrics make you want to hunt down the ex that hurt our Taylor. Please proceed with caution if you’re currently heartbroken.
8‘All You Had To Do Was Stay’ (2014)
Sure, this is a cracking song, but how are we supposed to cry when we’re busy vibing? Possibly the biggest track-list mistake in her career, track five on ‘1989’ undeniably should’ve been ‘Clean’, or ‘This Love’. Maybe in an attempt to fully separate from her country roots, Taylor was willing to sacrifice the lineage of tracks fives here?
7‘White Horse’ (2008)
Think Taylor Swift heartbreak songs, and ‘White Horse’ is probably the first that springs to mind. As much as Swifty insists that she’s no princess, and love isn’t a fairytale, she still gives a lot of airtime to a knight in shining armour (and his aforementioned steed) here. This comes at the expense of emotional heft, and so this one doesn’t qualify for track five greatness. Ultimately, this song doesn’t make its listener want to smash something in a cathartic rage. Look elsewhere when the heartache hits.
‘Delicate’, from ‘Reputation’, is a difficult one. Sure, it ticks the box of being intensely specific, introducing us to her current partner, the actor Joe Alwyn, with an infamous dive bar scene that returns again and again in future albums to come. It’s tender and sweet, and feels very close to Taylor’s heart in a way that’s true to the track five tradition. But it’s also quite cheerful, capturing the uncertainty and stomach-flutters of falling for somebody. In general ‘Reputation’ lacks a sad ballad, and track five doesn’t quite deliver on that front.
5‘Cold As You’ (2006)
Swift’s first ever track five, ‘Cold As You’ comes in heavy with the classic country heartbreak banjo; archetypal debut album era Tay-Tay. And as a first effort, this really lays down the template she’s stuck with ever since. Specific enough to make its unlucky subject shudder and packed full of sharp lyrics, it culminates in a truly huge chorus – by the end, you’ll probably be screaming “you never did give a damn thing, honey” as if your cowboy husband has just cheated on you. It’s deliciously melodramatic, and a line like “I’ve never been anywhere cold as you” remains a top 10 Taylor smack-down lyric.
4‘The Archer’ (2019)
In a track five mood but in a conspicuous public place where you’d rather not bawl your eyes out in an unseemly and snotty fashion? Stick on ‘The Archer’, which feels like the musical equivalent of getting the bus home with miserable, glazed-over eyes, tear-ducts stinging but holding out for home. “Who could ever leave me darling but who could stay” – what a heart-wrencher. The vague Stranger Things theme vibe is a bit of a curveball. Just imagine if this song had been on ‘Folklore’…
3‘Dear John’ (2010)
‘Dear John’ holds so much power that some fans utterly despise its (alleged) subject John Mayer, despite knowing very little about the man otherwise. This, folks, is what a track five is all about. With lyrics so cutting and so specific that John Mayer admitted to being “humiliated” by it, this song goes straight for the throat. It would be perfect if it wasn’t for the life-affirming lyric “I’m shining like fireworks over your sad, empty town“. We came here to cry, Taylor, not to feel better.
2‘All Too Well’ (2012)
If you believe the fans, Jake Gyllenhaal must have done something to upset Taylor Swift. Her relationship with the actor allegedly inspired ‘All Too Well’ and in the process unlocked some kind of feral power. Boasting Swift’s greatest bridge, ‘All Too Well’ builds and builds until you have no choice but to lose it when she sings “you call me up again / Just to break me like a promise”. The ultimate post-breakup big euphoric cry soundtrack, and one of the definitive track fives.
1‘My Tears Ricochet’ (2020)
Co-producer Jack Antonoff was spot on when he called ‘My Tears Ricochet’ Swift’s greatest track five to date. “I think it’s one of the best songs you’ve written,” he told her during a chat in the recent documentary Folklore: The Long Pond Studio Sessions. Written completely solo and host to some of her most gut-wrenching lyrics (“And if I’m dead to you, why are you at the wake?”), this song feels like Taylor’s ultimate track five. And you could see it in her face when she performed it for the doc – this is a song written out of pain.