44. End Game (2017)
The sense that Taylor Swift had slightly lost her grip on her own music during the making of Reputation was underlined by End Game, a messy attempt to bring together Ed Sheeran with rapper Future over an R&B track. The end result is disjointed and completely at odds with her usual watertight songwriting.
43. Today Was a Fairytale (2010)
A reworking of the songwriting tropes found on Love Story, produced for the soundtrack of romcom Valentine’s Day, Today Was a Fairytale is a minor entry in her singles discography: the melody is nothing special, the lyrical conceit feels overfamiliar.
42. Look What You Made Me Do (2017)
Clearly a fan of Carly Simon’s You’re So Vain, Swift had made great capital from playing on the public’s prurient interest in who her songs might be about, but Look What You Made Me Do represented the point where the balance shifted: stripped of the accompanying speculation – and, indeed, its self-referential video – there is not much of a song here.
41. Change (2008)
The unexpected sound of Swift singing about the struggles of being an indie artist – at the time, she was signed to Big Machine, a label set up specifically for her – was subsequently repurposed as a US Olympic theme. A bit generic in its attempts to get fists punching the air, it is not among her most distinguished early efforts.
40. Teardrops on My Guitar (2007)
You could tell that Swift wasn’t prepared to be confined by Nashville from the fact that her second single came in “pop” and “radio” (ie country) versions, the former ditching the mandolin and pedal steel. It was a move that managed to cause a degree of controversy, the last thing you might expect from this well-written but unexceptional song.
39. Back to December (2010)
A beautifully produced and subtly orchestrated ballad that never quite sets your pulse racing, Back to December is notable largely as the first Swift single to provoke speculation about which famous former beau it was directed at: in this case, Twilight actor Taylor Lautner.
38. The Story of Us (2011)
More romantic woe, this time set to music that indicated Swift was heading away from Nashville: chugging post-Strokes guitars and something approaching a post-punk disco beat dominate and there’s not a pedal steel or banjo to be heard. She would go on to make better singles than this in the same vein.
37. Red (2013)
The least appealing of the singles taken from 2012’s Red, the album’s title track is an attempt to bridge the gap between Swift’s past and future: banjo up against stammering electronic vocal effects, melodramatic orchestration and stadium rock chorus. Weirdly, the demo version, stripped of the song’s more epic production touches, packs a bigger punch.
36. Everything Has Changed (2013)
Swift’s first collaboration with Ed Sheeran was feathery, slightly cliched-sounding, middle-of-the-road acoustic pop as cutesy as its accompanying video, featuring a burgeoning romance between primary school-age Swift and Sheeran lookalikes.
35. Fearless (2010)
The title track of Swift’s second album came out almost two years after the album itself and the sense of slightly diminishing returns is hard to miss. It is certainly not a bad song, but the sucker-punch power of earlier singles such as Love Story is noticeably absent.
34. Mine (2010)
The sense that Swift was reaching the limits of the country-pop style that had made her famous haunted 2010’s Speak Now. Its first single was as well turned as ever, sprinkled with great lines – “You made a rebel out of a careless man’s careful daughter” – and yet still carried the faintest hint of retreading old ground.
33. Mean (2011)
The arrival of another of Swift’s lyrical obsessions – the opinions of that latter-day bugbear, the Haters. In this instance, they are “grumbling on about how I can’t sing”. Her rebuke is done with wit – “All you are is mean and a liar and pathetic and alone in life and mean” – although the song itself is musically lightweight.
32. Long Live (2011)
Yet another single from Speak Now, Long Live is notable in so far as it was rerecorded as a duet with Brazilian singer Paula Fernandes. It is an early example of the now-common practice of giving a single wider global reach by releasing it in multiple versions, adding guest appearances by artists who are big in different countries.
31. Sparks Fly (2011)
Sparks Fly is interesting largely as a demonstration of how Swift’s early songwriting style was formed: indistinguishable from the rest of 2011’s Speak Now, it was written when she was 16 – prior to her debut single, Tim McGraw – and dug out due to fan demand six years later, after an early live recording began to circulate.
30. Eyes Open (2012)
Taken from the soundtrack of the first Hunger Games movie, Eyes Open saw Swift experimenting again, this time with a country-free, alt-rock sound, big on the muddy guitars. It is intriguing rather than essential, the sound of an artist searching for a route out of a commercially successful style she had now fully exploited.
29. The Last Time (2013)
Still clearly trying different avenues in her search for a new direction, Swift here attempts big old post-Coldplay stadium rock balladry, complete with a guest appearance from co-writer Gary Lightbody of Snow Patrol and strings arranged by Arcade Fire collaborator Owen Pallett. Not bad, but less fun than the stuff she had recorded with Max Martin.
28. Ours (2011)
Ours is not the most striking song Swift has released – you rather get the feeling it became a single largely out of a desire to commercially rinse the contents of Speak Now – but it has a certain low-key charm, its production understated by the glossy standards of Swift’s country-pop output.
27. Tim McGraw (2006)
Swift’s debut single effectively set out her stall, albeit one she would subsequently overturn: relatable tales of teen romance – sung in a noticeably chewier accent than her later material – set to polished country-pop. It is all extremely well done and sold millions, but there is a reason Swift abandoned this style: you can see its limitations.
26. … Ready for It? (2017)
Blessed with the kind of impermeable hook noticeably absent from its predecessor, Look What You Made Me Do, … Ready For It? also featured Swift rapping – better than you might expect – and feels not unlike the dubstep-inspired I Knew You Were Trouble amplified to blockbuster levels: simultaneously ridiculous and satisfying.
25. You Belong With Me (2009)
When the video for You Belong With Me won an MTV music award, it provoked Kanye West’s famous onstage interruption. The song itself – well-written, more high school-isms, a little less impactful than its predecessor Love Story – had sold 7m copies: worth remembering when considering West’s delusional belief that his protest made Swift famous.
24. Sweeter Than Fiction (2013)
Again, Swift used a soundtrack appearance – this time for the frankly terrifying-sounding One Voice, a biopic of opera-singing Britain’s Got Talent winner Paul Potts starring James Corden – to try something new: bubblegum electropop, in collaboration with Jack Antonoff of Fun. It was Golden Globe-nominated, which is more than you can say for the film.
23. Should’ve Said No (2008)
Written when Swift was 16, lyrically Should’ve Said No is classic cheating country updated for the social media age: “You should’ve known that word of what you did with her would get back to me.” Musically, it’s a post-grunge stadium rock anthem wearing a cowboy hat as a matter of convenience.
22. Delicate (2017)
The musical flip side of Look You What Me Made Me Do and … Ready For It?, Delicate is every bit as concerned about the public perception of Swift – not least that it might affect her romantic life – but sets it to a gentle wash of electronics and equips it with a bulletproof chorus.
21. Bad Blood (2015)
Getting Kendrick Lamar in to guest on the re-recorded version of the Katy Perry-baiting Bad Blood proved to be a masterstroke – his verses are potent and effective – as did stripping back the arrangement, removing the “real” instruments and leaving only beats and electronics: the effect is to make the chorus seem even more anthemic.
20. Begin Again (2012)
Country fans seemed to breathe a sigh of relief when Begin Again followed We Are Never Ever Getting Back Together: here was evidence that Swift hadn’t entirely left her roots behind, in the shape of a soft-focus ballad flecked with keenly observed lyrical details, far better than anything on her previous album, Speak Now.
19. Safe and Sound (2011)
An anomalous collaboration with acclaimed alt-country duo the Civil Wars, also for the Hunger Games soundtrack, Safe and Sound suggests an imaginary alternative career path, in which Swift moved away from pop towards an earthily simplistic, folky style. It was obviously never going to happen, but Safe and Sound is eerie and atmospheric enough to make you think she could have made it work.
18. Wildest Dreams (2015)
Swift effectively does Lana del Rey’s moody, synth-laden schtick, with a smart, pleasing twist. Instead of the default Del Rey position of weeping after a bad-boy boyfriend, her ex is presented as the victim, endlessly haunted by memories of the failed relationship.
17. Our Song (2007)
Bedecked with fiddle and banjo, filled with worries about someone’s momma and cries of “amen”, the self-penned Our Song was aimed squarely at the country market, but the snappy, self-referential lyrics were an early indication that Swift was a smart writer unwilling to deal exclusively in country cliches.
16. Gorgeous (2017)
Unassuming by the standards of the singles that immediately proceeded it, but somehow more appealing, Gorgeous boasts a lovely Abba-esque melody and a lyric that sounded noticeably more, well, lyrical than your average pop track in “you should think about the consequence of your magnetic field being a little too strong”.
15. Me! (2019)
What you might call standard Swiftian topics – “I know that I’m a handful” etc - cannily recast in primary colours and references to children’s books and TV (“spelling is fun!”, “one of these things is not like the others”) and given a post-This Is Me celebrate-your-individuality twist.
14. New Romantics (2016)
It says something about how overstuffed with potential hits 1989 was that New Romantics was relegated to special-edition, bonus-track status. In anyone else’s hands, its galloping urgency and vague hint of the electropop once purveyed by the musical subculture alluded to in its title would have made it the lead-off single.
13. White Horse (2008)
The second huge hit from Swift’s second album Fearless, White Horse is a big weepie ballad, but done with impressive subtlety: is there a more downbeat, underwhelming form of triumph than the chorus’s climactic cry of: “I’m gonna find someone someday who might actually treat me well”?
12. Ronan (2012)
A one-off charity single inspired by a blog in which Maya Thompson – credited as the song’s co-writer – detailed her three-year-old son’s fight against neuroblastoma. What’s striking about Ronan is how fully Swift, who wrote the song when she was 21, inhabits the character of a mother mourning her son; the lyrics are genuinely moving rather than mawkish.
11. We Are Never Ever Getting Back Together (2012)
The artistically underwhelming Speak Now clearly prompted a rethink: out went the last vestiges of Swift’s country past and in came pop super-producers Shellback and Max Martin. She sounds revitalised – smarter, snarkier and tougher, without losing her connection to her teenage audience – on a song laden with hooks.
10. Out of the Woods (2016)
Another collaboration with Antonoff – this time in full-on We Are Young bombast mode – Out of the Woods attracted attention because of the belief that it was about One Direction’s Harry Styles. In reality, it is a fantastic song that transcends the accompanying gossip.
9. New Year’s Day (2017)
Unexpectedly, one of the best singles off Reputation turned out to be one that Swift could have recorded a decade before: a piano-led, largely acoustic depiction of the morning after the night before that boasted a charm that seemed to evaporate when she became too lyrically transfixed on her media image.
8. Fifteen (2009)
The key to Swift’s early success lay in the watertight structure of her songs and the fact that her lyrics felt like realistic reflections of adolescence, rather than something focus-grouped to appeal to teenagers. Both factors are evident in Fifteen: its depiction of teen life, replete with poor old Abigail losing her virginity to a bad lot, seems guileless and unforced.
7. Style (2014)
Style’s exquisitely done homage to widescreen 80s drive-time rock opens with a riff that vaguely recalls Chaka Khan’s Ain’t Nobody, achieves lift-off when it hits the chorus – complete with Moroder-esque synth – and features a lyric that offers an intriguingly ambiguous depiction of a toxic relationship.
6. I Knew You Were Trouble (2012)
Swift apparently asked Shellback and Martin to make I Knew You Were Trouble sound “chaotic”. They duly obliged: it lurches from taut new wave-ish guitars to a controversy-causing dubstep-influenced chorus to sections that recall her ballads. Held together by a sparkling melody, it works as a pop song and a statement of artistic intent.
5. Picture to Burn (2008)
An early example of what has become one of Swift’s most celebrated songwriting tropes. A hapless ex is, metaphorically speaking, kicked in the cojones for three minutes as Swift embraces the image of a vengeful fury: “Go tell your friends I’m obsessive and crazy, that’s fine.”
4. 22 (2013)
Pure pop, from its fizzing chorus to the vaguely rave-influenced synths that drive it along, 22’s melodic sweetness, party-starting atmosphere and self-referentiality – “who’s Taylor Swift anyway? Ew!” – hides a smart examination of the moment when adulthood finally encroaches on your life: “We’re happy, free, confused and lonely … it’s miserable and magical.”
3. Shake It Off (2014)
Its impact has been a little dulled by its ubiquity, but it is worth pointing out that Shake It Off became ubiquitous only because it is a completely irresistible pop song: a hint of Toni Basil’s Mickey in its rhythmic DNA, a chorus you can’t dislodge from your brain, and lyrics that tell our old friends the Haters where to get off with sharp-tongued wit.
2. Love Story (2008)
Perhaps the moment when Swift’s songwriting prowess first fully revealed itself. A classic Springsteen-esque “let’s-quit-this-deadbeat-town” narrative from the perspective of a high-school girl, Love Story is a fantastic song. And if the references to Shakespeare and Hawthorn seem clumsy, they are clumsy in a believably teenage way.
1. Blank Space (2014)
It was perhaps inevitable that Swift’s transformation from Nashville-approved teen country sensation to mainstream pop star would be accompanied by a degree of pearl-clutching on the part of some commentators. But the really striking thing is how little she lost in the process. Blank Space is a perfect case in point: produced by Martin and Shellback, driven by synths, it still bears all the hallmarks that made her famous in the first place. The melody sounds effortless, the lyrics are sharp and funny and self-deprecating, the end result is a pop song so strong it has withstood covers by everyone from Imagine Dragons to Ryan Adams to Father John Misty doing an uncannily accurate impersonation of Lou Reed.
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