Taylor Swift released her first album 18 years ago. Since then, she’s been a country darling, a pop mega-star, and a quarantine savior; she’s sold 100 million albums worldwide and won 14 Grammys, including Album Of The Year four times (the first artist to ever pull off that feat). But her greatest accomplishment is providing the soundtrack to the lives of her faithful Swiftie listeners. Swift’s songs have gotten me through hard times, and she’s made the good times even better. She has a unique ability to connect to her fans, whether through her songwriting or on social media (she was an early and frequent presence on MySpace, Tumblr, and Twitter). It’s the main reason why nearly two decades into her career, she’s more popular than ever.
With her 11th studio album The Tortured Poets Department out now, it’s a good time to refresh the ranking of Taylor Swift’s best 50 songs, which was originally published in early 2021. Why 50? Because I couldn’t make it through her 200-plus songs without sobbing. (I couldn’t make it through the top 50 without crying, either, but it’s more manageable.)
Are you ready for it? Let the games begin.
50. “Tim McGraw” (Taylor Swift)
I remember the first time I heard Taylor Swift. It was the summer between my freshman and sophomore years of college, during that weird transitional period of your life when you’re settling on an identity for your adult self. My reunited high school friends and I were hanging out and drinking beers in someone’s basement. They all went upstairs to grab another 24-pack of Coors Light, while I stayed downstairs where the radio was playing. The music was background noise with my buddies around, but now that I was by myself, I started to concentrate on the song on the radio: “But when you think ‘Tim McGraw’ / I hope you think my favorite song / The one we danced to all night long / The moon like a spotlight on the lake.” I had to wait until the song was over to find out who it was, but I was hooked. Over 15 years later, I still am.
49. “Wildest Dreams” (1989)
The ability to evoke a specific (ahem) era of her life — and by proxy, ours — through her music is one of the reasons why Swift’s popularity has endured for so long. Take, “Wildest Dreams,” the breathy single from 1989. It sounds extremely mid-2010s (Taylor must have been listening to a lot of Lana Del Rey and Beach House around this time), but it’s not grounded in that time period, either. It’s an enduring cinematic ballad about a doomed relationship.
48. “Change” (Fearless)
Even in 2008, it was a weird fit to have Taylor Swift on the same compilation album as the Goo Goo Dolls and Nelly. That album, AT&T Team USA Soundtrack, was put together for the 2008 Summer Olympics. Swift didn’t write “Change,” one of the hardest-rocking songs in her catalog and first top-10 song on the Billboard Hot 100, specifically with the Olympic Games in mind. But it has an underdog origin that many Olympic athletes can surely relate to. Swift signed to Big Machine Records when she was still a teenager. At the time, she was the only artist on the label, and “I began to understand that it would be harder for me on a smaller record label to get to the places and accomplish the things that artists were accomplishing on bigger record labels,” she said. Still, Swift stuck with Big Machine and started writing “Change” about her “uphill climb” as an artist. The song remained unfinished until the 2007 CMAs, where she saw label president Scott Borchetta crying after she won an award (her feelings for Borchetta have since soured). “That’s when I finished [the song], because I knew I couldn’t finish it until something like that happened. It was absolutely the most amazing night of my life, getting to see the emotion of all the people who worked so hard for me,” Swift explained. “So I wrote that song about that.” “Change” would later appear as the final track on Fearless, but Swift would never forget where she came from (track two behind a halfway-decent 3 Doors Down song).
47. “Lover” (Lover)
How many Taylor Swift-loving couples have played “Lover” at their wedding? Hundreds? Thousands? The beautiful title track from Swift’s brightest album is made for slow dances under outdoor string lights (this scene from The Leftovers finale, basically). “Can I go where you go? / Can we always be this close?” she sings to her, her, her, her lover. “Lover” is about domestic bliss and looking forward to a life of contentment. But if the first dance never ends, that’s OK, too.
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46. “Our Song” (Taylor Swift)
“Our Song” was made for road trips with the windows down, barbecues on sunny days, and long days at the pool. It’s an upbeat number about a young couple who seemingly have it all, except a song. “But he says, ‘Our song is the slamming screen door / Sneakin’ out late, tapping on your window / When we’re on the phone and you talk real slow / ‘Cause it’s late and your mama don’t know.” It’s young love at its most innocent, and the final song on her debut album because, as Swift wrote long ago on her website, “the last line of the chorus is `play it again.’ Let’s hope people take it as a hint to go ahead and play the album again!” (They did.) If the young, exclamation point-loving Swift had any idea that “Our Song” would become “our song” for other young lovers, she might have added a few more !!!s.
45. “Mr. Perfectly Fine” (Fearless) (Taylor’s Version)
It was casually cruel of Taylor to not include “Mr. Perfectly Fine” on Fearless. It has an intoxicating hook and memorable chorus: “Hello, Mr. Perfectly Fine / How’s your heart after breaking mine?” The way she sings “the best seat, in the best room” with a scoff gets me every time. “Mr. Perfectly Fine” proved that her vault songs weren’t left off the original albums because they weren’t good enough; they are more than perfectly fine.
44. “mirrorball” (folklore)
“mirrorball” is the soundtrack to the world’s saddest disco. Gently sway along as Swift spins in her tallest heels, shining not for herself but just for you. “mirrorball” reminds me of a part in the Netflix documentary Miss Americana where Swift mentions that female artists have to constantly reinvent themselves to stay relevant in the misogynistic music industry, like a “new toy.” With deep resignation, she offers to “change everything about me to fit in,” but through it all, she’s “still a believer,” even if she doesn’t know why. All any of us can do is “try, try, try.”
43. “Loml” (The Tortured Poets Department)
I’m a sucker for a Taylor Swift piano ballad. “Loml” is the quietest song on The Tortured Poets Department, but her hushed vocals pack quite the punch. She’s mourning the end of a legendary relationship that ended up being momentary: “You shit-talked me under the table talking rings and talking cradles / I wish I could un-recall how we almost had it all.” By the end of the song, “Loml” has curdled from “love of my life” into “loss of my life.” Ouch.
42. “The Archer” (Lover)
“The Archer” was when I knew everything was going to be OK. “Me!” and “You Need to Calm Down,” the first two singles from Lover, left something to be desired. Was she in a creative spiral? Hardly. “The Archer,” the third single, is Taylor Swift at her most confessional, which is to say, Taylor Swift at her best. I still get chills when she switches from “they see right through me” to “I see right through me” over the throbbing synth and kick drum. She’s been the archer and she’s been the prey, but as long as she keeps writing songs as good as “The Archer,” I hope Taylor never goes away.
41. “You’re On Your Own, Kid” (Midnights)
Stevie Nicks took time during one of her concerts to praise Taylor Swift for writing Midnights standout “You’re On Your Own, Kid.” While describing the sadness she felt following the death of Fleetwood Mac bandmate Christine McVie, Nicks said, “Thank you to Taylor Swift for doing this thing for me, and that is writing a song called ‘You’re On Your Own, Kid.’ That is the sadness of how I feel.” She added, “I’m having to learn to be on my own, kid, by myself. So, you help me to do that. Thank you.” If the woman who penned “Silver Springs” is thanking you for your lyrics, you did something right.
40. “Death By A Thousand Cuts” (Lover)
No current songwriter pens a better bridge than Taylor Swift, and the twinkly “Death By A Thousand Cuts” is her most underrated. It didn’t immediately grab me like “All Too Well” or “Cruel Summer,” but once it did, I was a changed person. Where the rest of the track bubbles and pops, the “ranting bridge” on “Thousand Cuts” is pure breathless resolve: “My time, my wine, my spirit, my trust / Tryna find a part of me you didn’t take up / Gave you so much, but it wasn’t enough / But I’ll be alright, it’s just a thousand cuts.” A Taylor Swift bridge hits differently (so does “Hits Different,” but we’ll get there).
39. “this is me trying” (folklore)
Taylor Swift’s best songs are about specific experiences, but they resonate to her millions of listeners because they deal with universal feelings. For instance, “this is me trying” is about Swift’s state of mind in 2016 and 2017, when she felt like she was worth “absolutely nothing” and retreated from the public eye. That’s the specific. But attempting to open up to someone even when you don’t know what to say, other than, “I just wanted you to know that this is me trying”? That’s universal. “this is me trying” is a tough listen. It’s full of self-doubt and regret, like how I regret that the song came out in 2020 and not when I was in high school. “I got wasted like all my potential” would have been my AIM away message for years.
38. “I Bet You Think About Me” (Red) (Taylor’s Version)
Reputation has the most references to drinks, but it’s “I Bet You Think About Me” that will go down as Taylor’s best drinking song. It begins the way all the best dive bar tunes do: sh*t talking an ex- in the wee small hours of the morning. “3 a.m. and I’m still awake, I’ll bet you’re just fine / Fast asleep in your city that’s better than mine / And the girl in your bed has a fine pedigree / And I’ll bet your friends tell you she’s better than me, huh,” she sings, sounding more sarcastic than hurt. Personally, I can’t think of a better last-call drinking partner than Chris Stapleton.
37. “Dear John” (Speak Now)
Track five holds a special place in the heart of every Taylor Swift fan. It’s the emotionally devastating centerpiece of her albums. “I didn’t realize I was doing this, but as I was making albums, I guess I was just kind of putting a very vulnerable, personal, honest, emotional song as track five,” she said. In other words, if you’ve ever uncontrollably sobbed while listening to a Swift song (guilty!), it was probably to a track five. “Dear John” was her first track five masterpiece — it’s also her second longest song ever, and there’s a lot happening in those six minutes and 43 seconds. Generally, it’s about an older guy manipulating a younger woman; expressly, it’s about (allegedly?) John Mayer being a dick to Swift. He should have gone into the witness protection program after, “All the girls that you’ve run dry have tired lifeless eyes.”
36. “betty” (folklore)
When folklore was released, there was a lot of conversation about how “betty” was Swift’s queer anthem and that maybe, just maybe, it confirmed the rumors that she was bisexual (this speculation about her sexuality has always been a little weird to me; her people agree). “Betty, one time I was riding on my skateboard / When I passed your house / It’s like I couldn’t breathe,” she sings in the first verse. But the “I” in the lyrics isn’t Swift; it’s Swift singing as 17-year-old James, who “has lost the love of his life basically and doesn’t understand how to get it back,” she explained. “I think we all have these situations in our lives where we learn to really, really give a heartfelt apology for the first time. Everybody makes mistakes, everybody really messes up sometimes.” Swift once sang that she had “no time for tears” over a high school breakup because she’s “just sitting here planning my revenge,” but in “betty,” she flips the perspective. She’s now the one racked with guilt for the “worst thing that I ever did.” Does James deserve forgiveness? Will he ever kiss Betty on the porch in front of all her stupid friends again? That nuanced ambiguity highlights Swift’s evolution as a songwriter. Also, a harmonica makes every song better. I don’t make the rules. It just is.
35. “Would’ve, Could’ve, Should’ve” (Midnights)
“Would’ve Could’ve Should’ve” is the song I listened to the most while working on this ranking. Every time I clicked play on the Midnights bonus track, I would enter a trance-like state and not be snapped out of it until Taylor, her voice strained from vulnerability, sings, “Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first.” It’s like stumbling upon a movie on cable that you tell yourself you’re only going to watch until the next commercial. Then [SpongeBob SquarePants voice] four hours later, you’ve gone straight from The Fellowship of the Ring into The Two Towers. “Would’ve Could’ve Should’ve” is my precious.
34. “Shake It Off” (1989)
“Shake It Off” is Taylor Swift’s bar/bat mitzvah song. “What’s a bar mitzvah song?” you’re rightfully wondering. It’s a term I made up (that has decidedly not caught on) to describe a song that will get everyone, from nine-year-old kids to 90-year-old grandparents, on the dance floor at the bar/bat mitzvah. Or quinceañera. Or sweet sixteen party. It’s an omnipresent earworm. Other examples include “Get Lucky” by Daft Punk, “Happy” by Pharrell Williams, “Single Ladies (Put A Ring On It)” by Beyoncé, and “Hey Ya” by Outkast. You don’t need to hear “Shake It Off,” which kicked off Swift’s pop mastermind phrase, ever again, but when it comes on, you can’t resist it.
33. “Red” (Red)
I often think about this tweet, from back when they were still called tweets: “Is there a line reading from a film that continually pops up in your brain like a catchy lyric?” Mine is the way Gaston says “crazy old Maurice” in Beauty And The Beast, but that’s besides the point. I bring up this Very Good Tweet, because it works for songs, too. “Red” is not my favorite Taylor Swift song (it’s up there, though!), but it does feature one of my favorite moments in any Taylor Swift song. It comes about 2:30 minutes into the track, when Swift howls “burning it was red” over a searing guitar solo. It’s a moment of catharsis two-thirds of the way through one of her most subtly important songs. Before “Red,” Swift was afraid to leave the comfort zone of her first three albums, but “when I wrote that song, my mind started wandering to all the places we could go,” she explained. “If I were to think outside the box enough, go in with different people, I could learn from and have what they do rub off on me, as well as have what I do rub off on them.” Without “Red,” her career might look – and sound — a lot different.
32. “Don’t Blame Me” (Reputation)
When Taylor sings “I get so high,” she means it. She gives a towering vocal performance on “Don’t Blame Me,” a Reputation deep cut that found a second life on TikTok before becoming a highlight of the Eras Tour and subsequent concert film (a $20 tip for the first DJ to play the “Don’t Blame Me”/”Look What You Want Me Do” mashup in the club). She sounds like a preacher giving a fiery sermon to her flock — it’s Taylor’s “Like a Prayer.”
31. “Anti-Hero” (Midnights)
Is “Anti-Hero” Taylor’s most iconic chorus? Not necessarily the best, but the most well-known, the one that’s so buried into the collective consciousness that, to use another example, you can’t hear someone say “we’re halfway there” without wanting to add “living on a prayer.” Under that guideline, I lean towards “Shake It Off,” only because “it’s me, hi” is a frequent enough expression in casual conversation. Taylor is synonymous with “haters gonna hate, hate, hate, hate, hate.” But “Anti-Hero” is a close (and catchy) second.
30. “Mean” (Speak Now)
I love a good kiss-off song. If it sounds like a backyard hootenanny, even better. “Mean” is one of the catchiest-yet-vicious songs in Swift’s discography, with cutting lines like, “You, with your voice like nails on a chalkboard / Calling me out when I’m wounded / You, picking on the weaker man.” Swift penned “Mean” after a music journalist (widely thought to be Bob Lefsetz) wrote that she killed her career following a performance at the Grammys with Stevie Nicks where she sang off-key, and that she was “too young and dumb to understand the mistake she’d made.” Swift told CBS News that the things “this dude” said about her “just floored me and like leveled me.” “Mean” is her “Positively 4th Street,” her “Get In The Ring” (minus the spoken-word rant), and if you claim to not like it, you’re a liar, and pathetic, and alone in life…
29. “happiness” (evermore)
I can’t casually listen to “happiness” in public. I don’t want to start crying around strangers. “happiness” is a slow haze of a song, possibly written with The Great Gatsby in mind. Does Swift take Jay Gatsby telling Daisy Buchanan that she’ll “always have a green light that burns all night at the end of your dock” and turn it into “all you want from me now is the green light of forgiveness”? Maybe! Or maybe it’s just a good metaphor. Good song, either way.
28. “Should’ve Said No” (Taylor Swift)
“Should’ve Said No” was a last-minute addition to Swift’s self-titled debut. She was all of 16 years old when she wrote this angsty up-tempo song, which was inspired by “something really, really dramatic and crazy” that happened to her at the time (her boyfriend cheated on her). Swift needed “to address it in the form of music,” because that’s the difference between Taylor Swift and everyone else: she writes songs to cope; we listen to Taylor Swift’s songs to cope.
27. “‘tis the damn season” (evermore)
Taylor’s best holiday song isn’t “Christmas Tree Farm” or anything on The Taylor Swift Holiday Collection (still waiting on that Taylor’s Version). It’s “‘tis the damn season.” She never mentions Christmas by name, but through her sorrowful lyrics, she evokes the melancholy feeling of the supposed most wonderful time of the year. Listen to this song when you’re flying back to your hometown where your ex- still lives for maximum impact.
26. “Guilty As Sin?” (The Tortured Poets Department)
Taylor Swift hasn’t done anything “wrong” in “Guilty As Sin?” But she’s tempted to. The Tortured Poets Department highlight finds Taylor longing for someone who she won’t allow herself to be with. It might be because she’s in an existing relationship that feels like a cage, or maybe she’s just afraid of how she’ll be perceived for being with this person. To cope, she keeps “these longings locked in lowercase inside a vault / Someone told me there’s no such thing as bad thoughts, only your actions talk.” But she can’t stop thinking about him, especially in the bedroom: everything they could do, she’s “already done it in my head.” It’s make believe, but it feels so real (and a good reminder that “Downtown Lights” by The Blue Nile is a classic).
25. “Enchanted” (Speak Now)
I still think it’s extremely rude that Taylor Swift only included one song from Speak Now into every Eras Tour show, but at least she picked a good one. “Enchanted” is about “a guy who I was enchanted to meet, obviously,” she explained years ago. “He was somebody that I had talked to a couple of times on email, and then I was in New York and went to meet him. I remember just the whole way home thinking, I hope he’s not in love with somebody.” The guy is suspected to be Owl City’s Adam Young, who later covered “Enchanted” as a response to Taylor with some minor lyrical tweaks: “Oh, Taylor, I was so enchanted to meet you, too.” He never heard back, but at least he got a fairytale-like ballad (and a perfume) out of it.
24. “Clean” (1989)
Swift tends to collaborate with the same people multiple times: professional songwriter Liz Rose, Bleachers frontman Jack Antonoff, pop music genius Max Martin, the National’s Aaron Dessner, Grammy-winning producer Shellback. But she only worked with electropop icon Imogen Heap once. They should have penned more songs together: they’re batting 1.000 with 1989 closer “Clean,” which effectively mimics the moment you realize you’re over someone. One second, the breakup clings to you “like a wine-stained dress I can’t wear anymore.” The next, gone was any trace of the relationship. It took a flood of emotions to get there, but you’re finally clean.
23. “New Year’s Day” (Reputation)
It’s tempting to think that you’re with The One on December 31 when the booze is flowing and the mood is joyous. But what about on January 1? It’s a new year, but you’re left with the figurative remnants of last year’s you — and the literal mess from the party. Will The One still be there? He wasn’t in “The Moment I Know” from Red. He missed the party entirely. But two albums later, Swift found someone who not only attended the New Year’s Eve party with her, he also helped her pick up bottles the next morning. Hold onto them like a memory.
22. “Blank Space” (1989)
Before the “mouth-f*ck you forever” misunderstanding from “mad woman,” there was “Starbucks lovers.” It’s impossible to hear “Blank Space,” with its chilly minimalist production, and not think of the intentionally over-the-top music video, where Swift leans into the circa-2014 public perception of her as an “insane,” knife-wielding jealous lover. Her mascara is smeared, she catches her blandly-handsome man texting another woman, she smashes his car with a golf club. She’s a nightmare dressed like a daydream. It’s effective satire, which of course many people missed. “Half the people got the joke, half the people really think that I was like really owning the fact that I’m a psychopath,” Taylor said at the time. “I have no complaints.”
21. “Fearless” (Fearless)
“Fearless” is about the thrill of firsts. The first date, the first kiss, the first dance in “a storm in my best dress.” It implores you to take a chance on an unknown, because even if it doesn’t work out, at least you had the experience. “Fearless doesn’t mean you’re completely unafraid and it doesn’t mean that you’re bulletproof,” Swift explained with the perspective of someone much older than her 20 years at the time. “It means that you have a lot of fears, but you jump anyway.” Here’s another first: “Fearless” is the first song on the 12-times platinum album (plus however-many-more from the Taylor’s Version edition) where country star Taylor Swift became crossover star TAYLOR SWIFT. She landed the jump.
20. “my tears ricochet” (folklore)
“my tears ricochet” is one of Taylor Swift’s finest vocal performances (it’s also the only song on folklore where she has sole writing credit). Her trembling voice sounds cracked at first, but she’s not ready to give in; as the bridge hits, her determination swells. “my tears ricochet” was inspired by Marriage Story, the Oscar-winning drama from Barbie co-writer Noah Baumbach starring Scarlett Johansson and Adam Driver as a couple going through a divorce. Swift has never been married, but while writing folklore, she found herself “very triggered by any stories, movies, or narratives revolving around divorce, which felt weird because I haven’t experienced it directly. There’s no reason it should cause me so much pain, but all of a sudden it felt like something I had been through.” Her tears ricocheted not for the end of a marriage, but for the culmination of her relationship with Big Machine Records.
19. “Getaway Car” (Reputation)
18. “Out Of The Woods” (1989)
17. “Cruel Summer” (Lover)
I don’t know how to separate these songs, which a Redditor accurately dubbed “the Antonoff Anthem.” Jack Antonoff has worked with Swift (and Lorde, Carly Rae Jepsen, Lana Del Rey, Tegan and Sara, FKA Twigs, The Chicks…) since 2013, including much of folklore and evermore, and these are his masterpieces. They’re big, propulsive anthems that are fun to scream — not sing, but SCREAM — along to. I love the way Swift twists the word “cruel” into knots and the rasp when she describes her man “grinning like a devil.” I love the chaotic repetition of “are we out of the woods yet?” I also love the behind-the-scenes video of Swift and Antonoff solving a lyrical riddle about motel bars and stolen keys. But seriously, where’s the “Cruel Summer” music video?
16. “You’re Losing Me” (Midnights)
“You’re Losing Me” begins with a heartbeat and an exhale, as if Taylor is warning us: get ready. But nothing can prepare you for “how long could we be a sad song / ’til we were too far gone to bring back to life?” The second of three bonus tracks on Midnights to make this list compares a dying relationship to a medical emergency (once a Grey’s Anatomy fan, always a Grey’s Anatomy fan). She can’t find a pulse, her heart won’t start anymore for you, you’re losing me. The heartbeat is present throughout the entire song, but once the other instruments fade away, it’s the only noise to fill the otherwise-deafening silence. The relationship has flatlined.
15. “Holy Ground” (Red)
I was reminiscing just the other day about the peak of the pandemic, when we all tried to find things that would distract us from the boredom and, y’know, constant depression and fear. For me, that was running. I ran more than I ever had before, often the same route. I wanted the miles, but I didn’t love the idea of planning a different route every day, so I ran the same streets — and listened to the same songs. On one hill, in particular, I would almost always play “Holy Ground.” The galloping beat made a strong accompaniment to my elevation-conquering plodding. If I timed it right, I would make it to the top by the first “holy ground.” And then I would spend the jog back down the hill wondering if she’s singing “ooh-ayy” or “hol-ayy” beginning in the bridge (apparently it’s “the sounds of my happy emotions” — the more you know!).
14. “Delicate” (Reputation)
“Is it cool that I said all that?” That’s not a question you often hear in pop songs. It’s “I Want To Hold Your Hand,” not “Can I Hold Your Hand?” But that tentativeness is what makes “Delicate” a modest (and, let’s face it, sexy) triumph. With her graceful vocals manipulated by a vocoder, Swift wonders what the new man in her life, the one in dark jeans and Nikes, has read about her. It’s a familiar anxiety for anyone with an active Twitter account when they’re applying for a job or going on a first date. But if they’re still interested after looking you up on Google, they must like you for you.
13. “Sparks Fly” (Speak Now)
In being “denied the chance to purchase my music outright” from Scooter Braun, who sold her master recordings for around $300 million, Swift announced in 2020 that she would re-record her first six albums (everything before Lover) to regain artistic and financial control. It’s been a fascinating (and successful) experiment for numerous reasons, including hearing the subtle differences someone who is now in her 30s brings to songs that her teenage self wrote and recorded. “Sparks Fly,” written at 16 and recorded at 20, is pure fairy-tale exuberance. As an adult, you know better (or at least you should know better) than to be with someone who deep down you know is a “bad idea.” But as an anything-is-possible teenager, you’re not thinking long term; you’re in it for the kisses in the pouring rain, the kind that you see in movies. Or hear in Taylor Swift songs.
12. “You Belong With Me” (Fearless)
Taylor Swift is one of the most successful songwriters of the past 20 years, but she’s had help along the way. Many of the best songs in the early stages of her career, including “You Belong With Me,” were co-written by Liz Rose, a Nashville veteran who’s also worked with Little Big Town, Carrie Underwood, and, fittingly, Tim McGraw. Rose told Billboard that the magic of “You Belong With Me,” an irresistibly effervescent mix of country, pop, rock, and high school tropes, is due in part to the mega-chorus and how it “makes you want to stay until the end of the song.” As the first single from her blockbuster sophomore album, that lively chorus — “IF YOU COULD SEE THAT I’M THE ONE WHO UNDERSTANDS YOU” (she’s singing with all-caps passion) — is Swift’s coming out party as a generational talent. We’ll be there until the end of the song, and beyond.
11. “Hits Different” (Midnights)
How did “Hits Different” not make the original album? How??? “Hits Different” — the best song to ever have the word “antithetical” in the lyrics — was first released as a bonus track on the Target-exclusive Lavender Edition of Midnights before making its streaming debut on the Til Dawn Edition. But all this confusion could have been avoided if “Hits Different,” which has a melancholic Swift reeling from a particularly messy breakup (“Now the sun burns my heart and the sand hurts my feelings / And I never don’t cry at the bar”) over a deceptively upbeat melody, had made the original tracklist. Maybe she was embarrassed about going to the club and throwing up on the street? Taylor, we’ve all been there.
10. “Long Live” (Speak Now)
Here’s what I wrote in my original write-up for “Long Live”:
“Long Live” is a triumphant power ballad that might be more well known if it played during the climactic scene in a The Fault In Our Stars-like teen movie (I would also accept the end credits of the Game Of Thrones prequel series with the lyric about having “the time of my life fighting dragons with you”). This hasn’t happened — yet — but Swift seems to like it, at least, as it was resurrected for the Reputation tour in a mashup with “New Year’s Day.”
I feel like I willed “Long Live” playing over the Taylor Swift: The Eras Tour end credits into existence?
9. “State Of Grace” (Red)
“State Of Grace,” a soaring stadium-ready anthem with shimmering guitars and pounding drums, should be track 1 on every Taylor Swift playlist. It’s a mood setter about “when you first fall in love with someone — the possibilities, kind of thinking about the different ways that it could go,” Swift explained. “It’s a really big sound. To me, this sounds like the feeling of falling in love in an epic way.” The word “epic” is thrown around a lot these days, but it’s applicable here. There is no other Taylor Swift song that sounds like “State Of Grace.” Why mess with perfection? It’s the best U2 song since “Beautiful Day.”
8. “Cornelia Street” (Lover)
While renovations were being done around 2016 on her New York City penthouse in Tribeca that was previously owned by director Peter Jackson, Swift moved into a townhouse on Cornelia Street. She didn’t live there for long (it also didn’t take TMZ too long to find her), but she’ll never forget her time in the West Village. “Cornelia Street” is a finely observed song about the indelible connections made between a person and a place. “I hope I never lose you, hope it never ends,” she sings, “I’d never walk Cornelia Street again.” The happy memories of sitting on the roof and being barefoot in the kitchen would wither if the relationship soured. The relationship did sour, but “Cornelia Street” still resonates with anyone who’s gone the long way to avoid the coffee shop where you and your ex used to go.
7. “champagne problems” (evermore)
“I love a sad song.” That’s the understatement of the century from Swift talking about writing “champagne problems.” This mournful track is about “longtime college sweethearts [who] had very different plans for the same night, one to end it and one who brought a ring,” as she described it. But there’s further depth to the song about privilege and first-world problems, a.k.a. “Champagne problems.” Rejecting a wedding proposal isn’t literally a life or death scenario, but it can feel like one in the moment. Especially if you say no. You can hear the voices in your head while the other person is still on their knee: “She would’ve made such a lovely bride / What a shame she’s fucked in the head.” Swift loves sad songs, and we love sad Taylor Swift songs.
6. “The Story Of Us” (Speak Now)
Inspired by an awkward encounter with an ex-boyfriend at an awards show, Swift put into words the “standing alone in a crowded room” feeling of being near someone who once meant so much to you, but now you’re purposefully ignoring one another. It’s the closest Swift has come to full-blown pop-punk (with an angsty country twang): “I’m dying to know / Is it killing you like it’s killing me?” One of her best karaoke songs.
5. “Style” (1989)
Swift has performed “Style” every time that I’ve seen her live (seven for seven), and without fail, it gets one of the loudest reactions from the crowd. The seductive 1989 single sounds big when played at full volume in the car, but it’s massive in a stadium, especially when Swift gets to the chorus. My god, that chorus. This thing explodes. “You got that long hair, slicked back, white t-shirt / And I got that good girl faith and a tight little skirt,” she sings (you can practically hear the wink) over a Daft Punk-inspired “funky electronic” groove. “Style” is the most 1980s-sounding of any of the 1989 songs.
4. “Is It Over Now?” (1989) (Taylor’s Version)
“Is It Over Now?” is about a man in Swift’s life — possibly the same guy who shares a last name with a song title on 1989, hm? — who has been two-timing her. “You dream of my mouth before it called you a lying traitor / You search in every maiden’s bed for something greater.” In the second verse, she appears to reference the “red blood, white snow” that led to 20 stitches in a hospital room (to say nothing of the “blue dress on a boat” imagery). To add insult to injury, the guy’s new girl looks exactly like Swift. “Is It Over Now?” fills in lore for Swift completists — and for normal people, it’s a damn good song, full of drama, clever turns of phrase, and a propulsive bridge. I wish “Is It Over Now?” was never over.
3. “New Romantics” (1989)
Taylor Swift is not exactly lacking for hits. She’s had 11 songs top the Billboard Hot 100 (“We Are Never Ever Getting Back Together,” “Shake It Off,” “Blank Space,” “Bad Blood,” “Look What You Made Me Do,” “Cardigan,” “Willow,” “Cruel Summer,” “All Too Well (10-Minute Version),” “Anti-Hero,” and “Is It Over Now?”), and a staggering 232 songs overall on the chart, the most for any female artist ever. That being said, it’s a crime “New Romantics” never cracked the top 10. Heck, it never got higher than No. 46 (even the Taylor’s Version, when everyone should have known better, only reached #29), despite sounding like pop music euphoria. Taylor has a chill distance to her voice during the verses, but once the chorus hits, she’s all glee. “New Romantics” is the perfect soundtrack to closing down the dance floor with your best friends.
2. “Love Story” (Fearless)
Or, the song in which Taylor Swift literally re-writes William Shakespeare. In “Love Story,” Swift depicts herself as Juliet, one-half of history’s most famous star-crossed lovers. The other half: Romeo, who she asks to “take me somewhere we can be alone.” She’ll be the princess to his prince, even against her family’s wishes; all he has to do is say “yes.” Everyone who read Romeo And Juliet in eighth grade knows what happens next, right? Wrong. In a plot and key change for the ages, Swift turns Shakespeare’s tragedy into a stirring ode to inevitable love.
1. “All Too Well (Red)
It’s always tempting to be a contrarian with these kinds of lists, to go against the near-unanimous consensus for an artist’s crowning achievement. Nah: “All Too Well” is the best Taylor Swift song. This thing was a masterpiece at 5 minutes, and it’s still a classic at 10 minutes.
“All Too Well,” which was written on a day when Swift was “feeling terrible about what was going on in my personal life,” is a masterpiece of details. The plaid shirt, the upstate sing-along, the photo of the little kid in glasses with a twin-sized bed — it’s a vivid montage of memories from a relationship that was magical “until you tore it all up.” Swift could have torn up the lyrics to “All That Well” on that fateful day she wrote it (with help from co-writer Liz Rose and producer Nathan Chapman). It could have been too raw, too much of an emotional scab that she wasn’t ready to pick at. But she released her head-banging catharsis into the world, and it turned into an anthem and her best song, one that everyone who hears it will remember all too well.