When we first published our ranking of Taylor Swift's best songs in October 2022, she was on the verge of releasing her 10th album, Midnights. Oh, how things have changed.
Since then, she's released re-recorded versions of Speak Now and 1989 for her Taylor's Version series, adding a pile of bonus cuts to each. And, even more importantly, her Eras Tour has been the biggest event in live music, as she has revisited and recontextualized songs from across her catalogue. (She also became a billionaire and the first musician named Time Person of the Year.)
With so much having evolved to make her into undeniably the biggest pop star in the world — and with the new album The Tortured Poets Department arriving tomorrow (April 19) — we're revisiting our list. We've expanded the list from 20 to 25 to reflect how much the past couple years have changed how we view her discography.
Given that her Eras Tour is still underway, and new LPs and more Taylor's Version albums in the pipeline, who knows how long this ranking will last. But for now, here are Taylor Swift's 25 best songs.
25. "Wildest Dreams"
1989 (2014)
"Say you'll remember me / Standing in a nice dress / Staring at the sunset, babe"
Combining the gothic luxury of "Young and Beautiful" with a chorus lifted from Born to Die deep cut "Without You," "Wildest Dreams" yassifies Lana Del Rey, as a sultry Swift purrs about getting tangled up in the sheets with a bad boy who's handsome as hell. She totally nails it, delivering an uncharacteristically randy torch song about how her lover will miss her once she's gone. Thanks to this song, these memories will definitely follow him around.
24. "22"
Red (2012)
"We're happy, free, confused and lonely in the best way"
Swift has a knack for writing songs that perfectly capture a specific age — like the fearful flights of imagination of "seven" or the romantic naïveté of "Fifteen." She captures "22" as a time of pure joy and excitement, when your friends mean everything and the future's possibilities still feel limitless. It's a miserable, magical time that Swift conveys with one of her hugest pop choruses ever.
23. "exile" (feat. Bon Iver)
folklore (2020)
"I think I've seen this film before / And I didn't like the ending"
As a general rule, Swift's duets are best forgotten (and that includes her weak and thankfully infrequent attempts at rap remixes). The very notable exception is "exile," with Bon Iver providing the comically deep intro verse as well as its heart-swelling bridges. It's a perfect showcase for Jason Vernon's evocative vocals, featuring some nimble call-and-response interplay between him and Swift. It's also Swift's best work with co-writer William Bowery. We wish him well!
22. "State of Grace"
Red (2012)
Taylor Swift goes... arena rock? Well, not quite. But with its anticipation-building intro of thunderous drums, distorted electric guitar strums and even some little squeals of feedback, Red opens with a heavier soundscape that she's ever made before or since. Evoking the cinematic, atmospheric surge of U2, it's the perfect heart-soaring accompaniment to some of Swift's most earnest lyrics about romantic possibilities.
21. "Cornelia Street"
Lover (2020)
"We bless the rains on Cornelia Street / Memorize the creaks in the floor"
Swift has always displayed a deft understanding of how specifics make stories universal. When you pair that with one of the most unexpectedly satisfying beat-drops in her catalogue, courtesy of Jack Antonoff, you get the understatedly effervescent love letter to love itself that is "Cornelia Street." Bookended by her direct (and super casual) admission of "I rent a place on Cornelia Street," over jaunty synths and a trilling keyboard line, she somehow manages to reference "Africa" by TOTO and develop unnervingly gorgeous polaroid lyrics in the same breath, the ink as indelible as the memories.
20. "cardigan"
folklore (2020)
"I knew you'd haunt all of my what-ifs"
This one-that-got-away love story applies the narrative technique of "show, don't tell" to songwriting. Swift packs her lyrics with cinematic images, including the very "All Too Well"-esque metaphor of a cardigan kicked under the bed. And, just like a fashionable art film, Swift leaves it open-ended, since it's never quite clear whether her prediction that "you'd come back to me" has actually come true. As the lead single from folklore, "cardigan" was the first taste of her new direction with producer Aaron Dessner of the National, flipping the script on Swift's past self-deprecating joke about "some indie record that's much cooler than mine."
19. "New Year's Day"
reputation (2017)
"Please don't ever become a stranger / Whose laugh I could recognize anywhere"
The sigh of relief at the end of reputation sees Swift return to the core of the one she fashioned for herself: being a whip-smart songwriter. Shedding all of the clamouring drum machines, "I'm Too Sexy" samples and features from both Ed Sheeran and Future, "New Year's Day" is a straight-laced piano ballad that seems to allude to the vengeance having all been in good fun, as she remembers what truly mattered behind closed doors: the memories that will hold on to you. "I want your midnights / But I'll be cleaning up bottles with you on New Year's Day," she sings, painting vivid scenes with starkly unguarded turns of phrase and further harkening a future (just not the rapper) of midnight-stroked returns like clockwork.
18. "Red"
Red (2012)
"Losing him was blue, like I'd never known / Missing him was dark gray, all alone"
Red is the moment when Swift began pivoting from her country origins into full-blown pop — and that shift happens in real-time on the title track. Beginning with banjo plucking that's pure country, the song turns into a stomping roots rocker with a perfectly straightforward metaphor comparing colours to emotions. It's in the post-chorus that Swift reveals the newest trick up her sleeve: stuttering, chopped up vocals that allude to the electronic dance pop she would soon dive into headfirst. It's a joyful first step into a new sound.
17. "The Story of Us"
Speak Now (2010)
"You held your pride like you should've held me"
On the best dance-country banger this side of "Cotton Eyed Joe," Swift captures the racing heartbeat, sweaty palms and clothing-fidgeting awkwardness of raucous silence and feeling alone in a crowded room. She only takes a chapter away from the punchy percussion and chugging guitars when she reaches the bridge, offering the pen to her former paramour only to take it back after the final chorus with an exasperated spoken declaration of "the end." And in some ways, that also signalled the beginning of Swift stepping away from her fiddles and banjo-strums to delve further into four-on-the-floors.
16. "Out of the Woods"
1989 (2014)
"The rest of the world was black and white / But we were in screaming colour"
"Out of the Woods" is a juggernaut, the quiet simmer of its verses accelerating into surging choruses, Swift's hypnotic repetitions of the title phrase conveying a pulsing intensity that takes on a new dimension during the hospital scene of the euphoric bridge. It feels like a polaroid blown up infinitely larger than its actual size, exemplifying the best of Swift's ability to make a moment into something everlasting.
15. "marjorie"
evermore (2020)
"All your closets of backlogged dreams / And how you left them all to me"
It's not that uncommon to lose a grandparent with whom you shared similarities, but the experience feels so singular. With fluttering, cyclical textures that call to mind Sufjan Stevens and a simmering electronic pulse, Swift's eulogy to her maternal grandmother, who inspired Swift's own pursuit of music, will move you regardless. Opera singer Marjorie Finlay's soprano is even sampled towards the end of the beautiful dedication, capturing the best of evermore's melting down of a grief-stricken winter into poetic catharsis.
14. "Blank Space"
1989 (2014)
"You can tell me when it's over / If the high was worth the pain"
To this day, "Blank Space" remains one of Swift's biggest power moves. She shook off the "maybe she's the problem" misogyny of writing songs about relationships and satirized her media casting as a serial dater bouncing from one handsome celebrity to the next and turned it into one of her biggest hits. With glamorously unreliable narration, "Blank Space" embodies shiny solipsism with minimal, percussion-driven production à la Lorde's Pure Heroine and winkingly wicked vocals, in full control of mining romance for content. It's gonna be forever or it's going to go down in flames — and she's never been afraid to name names.
13. "Lover"
Lover (2019)
"We could leave the Christmas lights up till January / This is our place, we make the rules"
After the futuristic, aggro synthpop of reputation, Swift did a full 180 with Lover's swooning title track. Amidst a cloud of wall-of-sound reverb, she sweetly celebrates the mundanities of domestic love, singing about letting friends crash in the living room and leaving the Christmas lights up a little too long. The waltzing feel is just a few harmonies short of full blown doo-wop, making for an absolutely classic piece of songwriting that's possibly her most retro-sounding track ever — although we question why her friends need to sleep in the living room. Surely she's got a guest bedroom?
12. "Getaway Car"
reputation (2017)
"Think about the place where you first met me"
Before Jack Antonoff was known for making boring albums with pop stars, he was known for making very good albums with pop stars — and he and Swift were at the peak of their collaborative powers on "Getaway Car." It's a glitzy synthpop banger, bringing high drama to a night of romantic intrigue and a gigantic chorus. It laid the groundwork for the glossy pop sheen she would continue to explore on Midnights (but without the same success).
11. "Fearless"
Fearless (2008)
"Run your hands through your hair / Absentmindedly making me want you"
I may not have had somebody tell me they loved me and believed them when I was 15, but I did spot my first "Fearless" foot tattoo at a music festival. It was two years earlier, at 13, when Fearless was released, and I ate, slept and breathed it, giving copies of the CD to multiple friends for their birthdays that year. While a lot of the individual songs on the album (and many a lyric about princesses and getting stuck in the friendzone) don't hold up quite as well in retrospect, as soon as those glimmering threads of mandolin kick in on the title track, the melody cracks open as undeniably as the rush of realizing you're braver than you think you are in someone's presence.
10. "Delicate"
reputation (2017)
"Is it cool that I said all that? / Is it chill that you're in my head?"
reputation still stands as Swift's most polarizing album. Although I suspect that was probably her plan all along, some of the choices she made — and songs as a whole, let's be real — remain entirely baffling. The electropop experimentation fully succeeds on "Delicate," the album's first glimpse of vulnerability from a shadow Swift preoccupied by the masks we wear in the name of upholding façades. Aside from tropical house beats and smoggy synths, her only disguise here is the vocoder she sings into, which lends a song about playing it cool an oddly pure, forlorn quality.
9. "Mean"
Speak Now (2010)
"All you are is mean / And a liar, and pathetic / And alone in life and mean"
What makes "Mean" so immensely satisfying is that Swift has already won. She imagines a strawman argument with a spiteful hater from her past, telling him that, someday, she'll be "livin' in a big old city" and "big enough so you can't hit me." Of course, everyone knows that, by 2010, Swift already was all of those things, and she savours this chance to punch down (making up for all of the listeners who will never get a chance for revenge on their own naysayers). She wrings a beautiful melody out of a dead-simple chord progression and promises to end the pattern of cruelty, singing, "I bet you got pushed around / Somebody made you cold / But the cycle ends right now / 'Cause you can't lead me down that road." But then, just one minute later, she breaks her own promise with unparalleled pettiness, prodding the critic as "a liar" and "pathetic" and "alone in life." Damn, Taylor — why you gotta be so mean?
8. "Our Song"
Taylor Swift (2006)
"Our song is the slamming screen door"
My favourite Taylor Swift anecdote is that she wrote "Our Song," her first chart-topping hit, for her Grade 9 talent show. I like to imagine whoever had the bad luck of performing after her, and how they probably did a crappy lip sync dance to "Hollaback Girl" or something. They must have felt deeply inadequate after hearing Swift's mind-blowingly well-written story of young love, which imagines the soundtrack of a teenage relationship as a slamming screen door, tapping on windows, and the quiet murmur of late-night telephone calls.
7. "the last great american dynasty"
folklore (2020)
"Free of women with madness, their men and bad habits / And then it was bought by me"
It takes a truly great storyteller to write a twist ending into a four-minute pop song. "the last great american great dynasty" tells the true story of Rebekah Harkness, a widowed mid-century socialite who freaked out the neighbours with her Bitch Pack of fabulous friends. In a stunning reveal in the final line of the bridge, Swift shares that she herself is the new owner of Harkness's Holiday House in Rhode Island, casting herself as the latest loud woman to upset the gossipy old-money elites.
6. "Would've, Could've, Should've"
Midnights (3am Edition) (2022)
"Give me back my girlhood, it was mine first"
"Would've, Could've, Should've" shows what Midnights would have, could have, and probably should have been if she hadn't worked with Antonoff on the whole tracklist. This bonus track, produced by folkmore collaborator Aaron Dessner, packs an emotional wallop that far outstrips anything on the core album. Returning to painful memories of a manipulative past relationship, Swift gouges listeners with lines about poison, dancing with the devil and memories that feel like weapons. It stings, but the sweetly soaring chorus is perfectly soft.
5. "Love Story"
Fearless (2008)
"I close my eyes and the flashback starts / I'm standin' there, on a balcony in summer air"
Love songs don't get much more classic than "Love Story," as Swift likens the song's central characters to the most famous protagonists in all of romantic literature, Romeo and Juliet. It takes the naïve giddiness of a middle school crush to the furthest extent possible, culminating in a proposal and an ascendent key change. It's all a bit juvenile — but it was one of the highlights of Swift's Eras Tour film, as well as an emotional gut-punch in The Bear, proving the song's enduring power for listeners of all ages.
4. "Style"
1989 (2014)
"You got that James Dean daydream look in your eye / And I got that red lip classic thing that you like"
Oops! Is my good-girl faith showing? This is such a tight little skirt! Whether it feels more plucked from the opening scene of an '80s movie or a Daft Punk album, the funk guitar-driven synthwave atmosphere of "Style" instantly conjures night driving. Swift's terse vocal delivery — especially in the second verse, when she sounds on the verge of tears repeating, "Some other girl" — sells the impossibility of the dream at hand. Likewise, the second half of the chorus brings in a minor chord to assure listeners that these two people coming back to each other won't ever find the outcome they're looking for — but hey, it makes for a perfect pop song.
3. "august"
folklore (2020)
"Back when I was livin' for the hope of it all, for the hope of it all / 'Meet me behind the mall'"
The crown jewel of folklore's teenage love triangle trilogy with "cardigan" and "betty," Swift shines brightest when she brings the character trope of the other woman (who has historically been done nothing but dirty) to life so empathetically. After all, what is she guilty of besides living for the hope of it all? Though doomed, the summer romance was just as real for her as it was for the couple that presumably prevails, as emphasized by the lush, cinematic outro, trailing off after an altered bridge, lost in bittersweet thoughts of what was — materializing its memory in images of rusty doors, empty wine bottles and sun-soaked skin — and what might have been.
2. "Cruel Summer"
Lover (2019)
"So cut the headlights, summer's a knife / I'm always waiting for you just to cut to the bone"
Co-written with arty electro-rocker St. Vincent, the dizzying vocal run in the chorus bears the unmistakable stamp of Annie Clark, but channeled into the straightforward synthpop that Swift does so well. "Cruel Summer" looks back on a fleeting summer relationship, presenting a series of snapshots from a brief fling: sneaking in through the garden gate, the glow of a vending machine, the shape of a new lover's body. But while the lyrics look back with wistfulness, the thumping beats and rave-y synths throw the listener right into headrush excitement of infatuation. How on earth "ME!" and "You Need to Calm Down" were chosen as singles instead of this remains a mystery. (Fan demand finally got "Cruel Summer" sent to radio in 2023, and it topped the Billboard Hot 100 more than four years after its initial release. It has since tied "Teardrops on My Guitar" as Swift's fifth-longest-charting hit of her career.)
1. "All Too Well"
Red (2012)
"And you call me up again just to break me like a promise / So casually cruel in the name of being honest"
When Swift finally released the legendary 10-minute version of "All Too Well" last year, it was a fun piece of fan service, but the main takeaway was that the original version was already absolutely perfect. Swift gives just enough information to place the listener inside of a breakup story that's as vivid as a movie: cold air, childhood photos, plaid shirt days, and a stunning image of "dancing 'round the kitchen in the refrigerator light." The 10-minute version revealed the bitterness behind this breakup song — the age gap, getting stood up on her birthday, either Jennifer Anniston or Anne Hathaway asking her what happened — but the original five-minute edit wisely omits these details, leaving a song that's more wistfully nostalgic in tone. While the love affair may have maimed, there are still sweet memories left to keep like a forgotten scarf.
