Taylor Swift released her self-titled debut album 15 years ago this October. In the decade-plus since “Tim McGraw,” the first song and first single from her first album, she’s been a country darling, a pop mega-star, and a quarantine savior; she’s sold 50 million albums worldwide and won 10 Grammys, including Album Of The Year twice (the first solo female artist to pull off that feat), 12 CMA Awards, and one Emmy; donated millions to charity; and starred in Cats. But her greatest accomplishment is providing the soundtrack to the lives of her millions of faithful 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 her social media (she was an early adopter to and frequent presence on MySpace, Tumblr, and Twitter), and that’s the main reason why 15 years into her career, she’s arguably more popular than ever.
With the upcoming anniversary, the Swift-inspired “Driver’s License” at the top of the charts, her “Love Story” re-recording out this week, and the acclaim from Folklore and Evermore still in the near-past, now seems a good time to rank Taylor Swift’s best 50 songs. Why 50? Because I couldn’t make it through her 170-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”
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 our buddy Ben’s basement. They all went upstairs to grab another 24-pack of Coors Light (obviously), while I stayed downstairs where the radio playing. The music was background noise with my friends 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 instantly hooked. Over a decade later, I still am.
49. “Wildest Dreams”
That ability to evoke a specific time of her life — and by proxy, ours — through her music is one of the reasons why Swift’s popularity has endured for 15 years. Take, “Wildest Dreams,” the breathy single from 1989 that sounds extremely mid-2010s (she was also listening to 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.
There are plenty of artists/bands who have released two great albums in the same year. But few artists/bands have released two great albums in the same year with both albums sounding unlike anything they have released before. Folklore (Uproxx‘s favorite album of 2020) and Evermore (it didn’t come out during the eligibility period, but I imagine it would have ranked high, too) are Swift’s rootsy “indie” albums. There’s an emphasis on cardigan-weather atmosphere and character-arc narratives over matching the pop maximalism of 1989, Reputation, and Lover. I slightly prefer Folklore, but Evermore is no slouch, including the late album highlight “Ivy.” It’s part of Evermore’s “unhappily ever after anthology of marriages gone bad that includes infidelity, ambivalent toleration, and even murder,” Swift wrote in a letter to fans. It sounds the way Folklore and Evermore’s album covers look, with stark, nature-heavy details of “roots in my dreamland” and “house of stone, your ivy grows / And now I’m covered in you.” It’s haunting.
47. “Should’ve Said No”
“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 the 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 great songs to cope; we listen to Taylor Swift to cope.
“Starlight” isn’t the most lyrically complex song (“And we were dancing, dancing / Like we’re made of starlight, starlight” is one of her more generic, if still effective choruses), but it is a character study precursor to Folklore and Evermore. But unlike anything from those albums, “Starlight” is ripe for the dance floor. Swift’s inspiration for the song came from a photo of Ethel and Bobby Kennedy, the grandparents of her then-boyfriend, Connor Kennedy. “I came across this picture of these two kids dancing at a dance. It immediately made me think of how much fun they must have had that night,” she said. “Starlight” does a splendid job of replicating the feeling of limitless teenage nights.
45. “Death By A Thousand Cuts”
No one writes a better bridge than Taylor Swift. There are multiple rankings of her best bridges online, and last year, one of the Swift fan accounts I follow on Twitter (yes, “one of”) had followers vote for their favorite. I expected another song to finish number one (I’ll get to it later in this ranking — much, much later), but it came in second behind “Death By A Thousand Cuts,” a song I mostly associated with a twinkly piano. In fact, I had never really considered the song’s bridge before, but once I did, I was a changed man. 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 just hits differently, y’know?
I love a good kiss-off song. If it sounds like a backyard hootenanny, even better. “Mean” is one of the more catchy-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…
43. “Cowboy Like Me”
I’ll admit that this song, which tells the tale of two bandits falling in love, didn’t grab me the first time I heard it. But a week later, I took a nap while listening to Evermore (an excellent nap album — this not an insult, it’s just very cozy) and “Cowboy Like Me” was playing when I woke up. It sounded like I was still in a beautifully hazy dream. Kacey Musgraves will be doing the world a disservice if she doesn’t cover “Cowboy Like Me” on her next tour.
“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 first album where country star Taylor Swift became crossover star TAYLOR SWIFT (the 12-times platinum Fearless is still her best-selling album). She landed the jump.
“For sale: baby shoes, never worn” is a six-word story that’s often attributed to Ernest Hemingway, but there’s a 99.9 percent chance that he didn’t write it. It’s unclear who to credit, though, so the Hemingway myth has endured. Whoever it was, they told a complete narrative in the length of a tweet. The same can be said of these 10 words: “You made a rebel of a careless man’s careful daughter.” There’s a novel’s worth of detail in that single line from the glittery pop-country stomper that is “Mine,” and unlike “for sale: baby shoes, never worn,” we actually know who wrote it.
40. “I Knew You Were Trouble”
Taylor Swift was plenty popular before Red, but she wasn’t considered “cool.” That was part of her appeal: she was genuine and vulnerable and a heart-on-her-sleeve romantic, none of which were seen as “cool” in the early 2010s (I’d argue things have changed in pop music since, partially because of Swift, but that’s an essay for another time). “I Knew You Were Trouble” was the first time I remember the trendy kids, the same ones listening to “some indie record that’s much cooler than mine,” paying attention to Swift. It’s easy to hear why: “Trouble” is a banger, one that’s aged better than most dubstep-indebted songs from this era. That bass drop still hits with the impact of a truck driving through a brick wall. Also, the screaming goat remix. Never forget the screaming goat.
How many Taylor Swift-loving couples have played “Lover” at their wedding? Hundreds? Thousands? The stunning title track from Swift’s most liberated 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 would be OK, too.
Swift tends to collaborate with the same songwriters multiple times. She’s penned numerous songs with Liz Rose (more on her later), Jack Antonoff (same), pop music genius Max Martin, the National’s Aaron Dessner, and Grammy-winning producer Shellback, among others. But she only worked with electropop icon Imogen Heap once. I would love to hear more from these two together, as they’re currently batting 1.000 with the 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, you’re drowning, but you can “finally breathe.” It took a flood of emotion to get there, but you’re finally clean.
I often think about this tweet: “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 coming 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,” there might be no 1989 or Folklore.
36. “Our Song”
“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 “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!” she wrote long ago on her website. If the young, exclamation point-loving Swift, writing for the high school talent show in her freshman year, had any idea that “Our Song” would become “our song” for other young lovers, she might have added a few more !!!s.
I can’t casually listen to “Happiness” in public. I don’t want to start crying around strangers, not to mention how difficult it is to blow your nose while wearing a mask. “Happiness” is a slow haze of a song, possibly written with The Great Gatsby in mind. Does Swift transform Jay Gatsby telling Daisy Buchanan that she’ll “always have a green light that burns all night at the end of your dock” into, “All you want from me now is the green light of forgiveness”? Maybe! Or maybe it’s just a good metaphor. All I know is, “green light of forgiveness” is also the name of a self-help book… like the kind of help that I need after listening to “Happiness.”
“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. The lights from the “mirrorball” bring happiness and joy to millions, but it’s a fragile object; if it breaks, it does so into a million pieces. The show must go on, though. It’s a feeling that Swift has returned to time and time again through her career, but rarely with the depth of “Mirrorball.” The song also 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.” She, with deep resignation, 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.”
Even in 2008, Taylor Swift on the same compilation album as 3 Doors Down, Goo Goo Dolls, and Nelly was a weird fit. 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 catalogue (it was also her 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 she won the Horizon Award at the 2007 CMA Awards and saw label president Scott Borchatta crying (her feelings for Borchatta 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 on a compilation album behind a halfway-decent 3 Doors Down song).
32. “Back To December”
I have never been particularly interested in obsessing over which famous ex-boyfriend Taylor Swift wrote [fill-in-the-blank song] about — with the exception of “Back To December.” It’s extremely funny that one of her prettiest and mournful songs (“Maybe this is wishful thinking / Probably mindless dreaming / But if we loved again, I swear I’d love you right”) is about Taylor Lautner, the Twilight star who isn’t Kristen Stewart and Robert Pattinson. That’s like if Mitski’s “Your Best American Girl” was secretly inspired by Rupert Grint (no offense to Rupert Grint). “Back To December” is also a rebuke to the inaccurate and sexist claim that she only wrote songs about guys who did her wrong. She’s the one doing apologizing here, albeit to — and I cannot stress this enough — The Adventures Of Sharkboy And Lavagirl in 3-D actor Taylor Lautner.
I just wanted to take another listen to “Exile,” which answers the question, “What if ‘Shallow,’ except instead of Lady Gaga and Bradley Cooper, it’s Swift and Bon Iver?”
30. “The Lucky One”
Whenever I listen to “The Lucky One,” I think of my favorite Britney Spears song, “Lucky.” (It’s not the best Britney song, mind you, but my favorite. Swift even covered it once. The best is “Toxic.” There is no debate here.) Beyond having the word “luck” in the title, obviously, both songs are about a famous person who looks like they have it all, but inside, they’re unhappy. It’s a familiar story made personal by experience: Swift and Spears are two of the most photographed singers on the planet, and they’ve both had their secrets “splashed on the news, front page.” At the time of the song’s release, Swift expressed her fear that “you’ll be walking down the street and your skirt will blow up and you’ll be in the news for three months,” but all the paparazzi and gossip is worth it to “get on a big stage and sing your songs.” “The Lucky One” could have been Swift plotting her escape from world-conquering fame, but she (and hopefully Lucky) preserved.
29. “Long Story Short”
Taylor Swift unsuccessfully acknowledged her history with Kanye West (and later, Kim Kardashian) on “Look What You Made Me Do,” the posturing first single from Reputation that came to define that album’s, well, reputation. But on “Long Story Short,” she’s moved on from the feud. “I tried to pick my battles ’til the battle picked me,” Swift sings over an appealingly glitchy beat, later adding, “I was in the alley, surrounded on all sides / The knife cuts both ways / If the shoe fits, walk in it ’til your high heels break.” It was a bad time, she played house with the wrong guy, but now she’s found someone who makes her truly happy (current boyfriend Joe Alwyn) and all the old drama seems silly in retrospect. Long story short, this time she’s ready for whatever comes next.
Red is my favorite Taylor Swift album because of songs like “Treacherous.” It wasn’t released as a single, she’s unlikely to perform it live again unless there’s a 10th anniversary tour (coming in 2022?!?), and it’s not even the song most associated with Harry Styles’ mis-quoted tattoo. But “Treacherous,” as well as other non-singles like “Holy Ground” and “I Almost Do,” hold Red together as her best front-to-back album. It’s her Revolver, the exquisite median between her bubblegum-country past and pop-superstar future. Fun fact: “Treacherous” was co-written by Dan Wilson, who also wrote “Closing Time” for his own band, Semisonic, and “Someone like You” for Adele.
27. “My Tears Ricochet”
“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 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.
26. “Holy Ground”
This is the most accurate review of “Holy Ground.”
WHY IS BEST TAYLOR SONGS TO GALLOP TO A THING AND WHY IS IT SO FUNNY BYE😭😭 pic.twitter.com/y1ovxubDtT
— joud💛💛 (@champagnerush13) January 30, 2021
My only complaint is that it should be in the top three, at least.
25. “Shake It Off”
“Shake It Off” is Taylor Swift’s bar mitzvah song. “What’s a bar mitzvah song?” you’re rightfully asking. It’s a song that will get everyone, from nine-year-old kids to 90-year-old grandparents, to the dance floor at the bar mitzvah. Or quinceañera. Or sweet sixteen party. Basically, “Shake It Off,” which kicked off Swift’s pop mastermind phase, is a song that everyone in the world knows. (Other recent examples: “Get Lucky” by Daft Punk, “Happy” by Pharrell Williams, “Single Ladies (Put a Ring on It)” by Beyoncé, “Hey Ya” by Outkast. They’re mainstays in every Google search result for “songs that get people dancing.”) If you asked 10 casual pop music listeners to name three Taylor Swift songs, I guarantee all 10 would include “Shake It Off” in the three. You don’t need to hear “Shake It Off” again, but when it comes on, you can’t resist it.
24. “New Year’s Day”
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 and a new you, 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 (probably Jake Gyllenhaal, who will show up again later) missed her party entirely. But two albums later, Swift has found someone who not only attended the party, he also picked up bottles with her on the 1st. “New Year’s Day” may sound simple (Swift is accompanied only by a piano, sparse guitar, and synth in one of her loveliest arrangements), but it’s dealing with complex emotions. Hold onto it like a memory.
23. “New Romantics”
Taylor Swift is not exactly lacking for hits. She’s had seven 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,” and “Willow”), and a staggering 128 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, despite sounding like pop music euphoria. “New Romantics” was also bafflingly left off 1989 (it appeared on the deluxe version), but it’s a perfect soundtrack to closing down the dance floor with your closest friends.
22. “Getaway Car” / 21. “Out Of The Woods” / 20. “Cruel Summer”
I don’t know how to separate these songs, the Jack Antonoff trifecta. The Bleachers founder has worked with Swift (and Lorde, and Carly Rae Jepsen, and Lana Del Rey, and Tegan And Sara, and FKA Twigs, and The Chicks, and…) since 2013, including much of Folklore and Evermore, but 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?”, and I 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?
19. “This Is Me Trying”
Taylor Swift’s best songs are about specific experiences, but they resonate because they deal with universal feelings. For instance, “This is Me Trying” is about how Swift was feeling in 2016 and 2017, “where I just felt like I was worth absolutely nothing” and she 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. There are nods to suicide and addiction, and it’s full of self-doubt and regret. Like how I regret that it 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.
18. “Blank Space”
Before the “mouth-f*ck you forever” misunderstanding, 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 someone who isn’t her, and 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,” she said. “I have no complaints.” Speaking of misunderstandings…
When Folklore was released, there was a lot of conversation about how “Betty” was Swift’s queer anthem (a more successful one than “You Need to Calm Down”) and that maybe, just maybe, it confirmed the rumors that she was bisexual. I mean, there’s a case to be made from the first verse: “Betty, one time I was riding on my skateboard / When I passed your house / It’s like I couldn’t breathe.” But the “I” 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 to Billboard. “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 / Was what I did to you.” 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, the harmonica makes every song better. I don’t make the rules. It just is.
16. “Sparks Fly”
In being “denied the chance to purchase my music outright” from Scooter Braun, who sold her master recordings for around $300 million, Swift announced last year that she’s re-recording her first six albums (everything before Lover) to regain artistic and financial control. It’s going to be a fascinating experiment for numerous reasons, but the thing that I’m most interested in is the subtle differences a 31-year-old will bring to the 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 a 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. Can she channel that same level of anything-is-possible youthfulness again? I can’t wait to find out.
15. “The Archer”
“The Archer” was when I knew everything was going to be OK. I like Reputation more than a lot of people, but if it’s not Swift’s weakest album, it’s only one spot above the self-titled album. “Me!” and “You Need to Calm Down,” the first two songs we heard from Lover, are also two of her least satisfying singles. 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, she’s been the prey, but most of all, she proved she was back with “The Archer.”
14. “Champagne Problems”
“I love a sad song.” That’s the understatement of the century from Swift talking about “Champagne Problems.” The mournful track, co-written by Alwyn, is on its surface about “longtime college sweethearts [who] had very different plans for the same night, one to end it and one who brought a ring,” as Swift described it. But there’s further depth to the song about privilege and first-world problems, a.k.a. “Champagne problems.” In the grand scheme of things, rejecting a wedding proposal isn’t a life or death scenario when there are starving kids, etc. etc. etc. But it can feel like it when you’re the one being proposed to, especially if you decline the invitation to marriage. “She would’ve made such a lovely bride,” they’ll say, if she wasn’t “f*cked in the head.” Eventually, the man in the song finds another woman whose picture he’ll keep in his wallet, leaving the original would-be bride alone with her unremembered champagne problems. Swift wasn’t kidding: she does love a sad song. But so does Alwyn. Maybe love won’t slip beyond their reaches.
13. “Long Live”
The most underrated Taylor Swift song comes in at lucky #13. “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.”
12. “Dear John”
Track five holds a special place in the heart of every Taylor Swift fan. It’s where she puts her songs that are peak-emotionally devastating. “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 while promoting Lover. In other words, if you’ve uncontrollably sobbed while listening to a Swift song (guilty!), it was probably a track five. “Dear John” was her first track five masterpiece — it’s also her longest song, period, and there’s a lot happening in those six minutes and 43 seconds. Generally, it’s about an older guy manipulating a younger woman; definitively, it’s about 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.”
11. “You Belong With Me”
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. And I think that it makes a song more personal.” 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 it with all-caps passion) — is Swift’s coming out party as a generational talent.
“Ronan” is a heartbreaking stand-alone single that Swift wrote about Ronan Thompson, who died from cancer when he was four years old. She learned about Ronan after reading a blog by his mom, Maya, who recounted her initial phone call with Swift. “The tears started pouring down my cheeks as soon as I heard her say those words [‘I wrote a song for Ronan’]. But her words didn’t stop there. Not only did she write a song for you, but she wanted to know if it would be alright to perform it on the nationally televised Stand Up 2 Cancer show which is on every major network and is seen in over 100 countries,” she wrote. “Ronan” is Swift’s best non-album track, even if it’s too much of a tearjerker to be an every-day listen. “You were my best four years.”
9. “The Last Great American Dynasty”
In his memoir Chronicles, Bob Dylan discusses how he revitalized his career in the late 1980s by, essentially, playing the guitar differently. “I never used this style, didn’t see that there’d be any purpose to it. But now all of a sudden it came back to me, and I realized that this way of playing would revitalize my world,” he wrote. That passage came to mind the first time I heard “The Last Great American Dynasty.” Swift opened up a whole new world for herself by juicing her songwriting with experiences that weren’t her own. “Dynasty,” for instance, is a character study about socialite Rebekah Harkness, once one of the richest women in America, whose Rhode Island-based “Holiday House” is now owned by Swift. She didn’t personally know Harkness, but through the richness of her lyrics (“They say she was seen on occasion / Pacing the rocks, staring out at the midnight sea / And in a feud with her neighbor / She stole his dog and dyed it key lime green”), it feels like they’re BFFs. They would have a marvelous time ruining everything together.
One more Britney anecdote: my first date was at a Britney Spears concert. It was the Oops… I Did It Again tour, and I had an elaborate plan to give my crush a necklace during the section of “Oops” where the astronaut gives Britney a necklace. “But I thought the old lady dropped it into the ocean in the end.” Well, baby, I borrowed $20 from my mom and got you a crappy necklace from the mall. (Also, I’m sorry for calling you “baby.”) I chickened out at the last second, however. The date was going terribly enough without my presentation of a cheap piece of jewelry to poor Allison. But it could have gone worse. I could have taken my date to the Speak Now tour and stared into her eyes during the part of “Enchanted” where Swift sings, “I was enchanted to meet you” before pleading, “Please don’t be in love with someone else.” I didn’t do this (even the fictional scenario makes me cringe), but I imagine many others have, as “Enchanted” is a romantic song about the anxiety that comes with wondering if your crush (in Swift’s case, Owl City’s Adam Young) is thinking about somebody else. Kind of like how my date Allison was thinking about being anywhere else that night.
7. “Cornelia Street”
While renovations were being done on her Tribeca penthouse previously owned by Lord Of The Rings 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 song’s probably about Alwyn, but it resonates with anyone who’s gone the long way to avoid the coffee shop where you and your ex used to go.
6. “State Of Grace”
“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 said on Good Morning America. “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 epic — and the best U2 song since “Beautiful Day.”
“Is it cool that I said all that?” That’s not a question you often hear in pop songs. It’s not “Can I Hold Your Hand?” It’s “I Want to Hold Your Hand.” But that tentativeness is what makes “Delicate” the one true masterpiece on Reputation and a top-five Swift song overall. 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.
4. “Love Story”
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 key change for the ages, Swift turns Shakespeare’s tragedy into a stirring (and catchy as hell) ode to inevitable love. No wonder (Taylor’s Version) is coming out in time for Valentine’s Day.
Swift has performed “Style” every time that I’ve seen her live (three for three), and without fail, it gets one of the loudest reactions from the crowd. The seductive 1989 single — and the one song from the album that sounds like it could have been released in the 1980s — 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. With songs this good, Swift will never go out of style.
2. “The Story Of Us”
Shakespeare might not have enjoyed “Love Story,” but I bet he would have gotten a kick out of the tragedy in “The Story Of Us.” (He wishes the story had been told in five acts, but long-dead beggars can’t be long-dead choosers.) Inspired by an awkward encounter with an ex (Mayer, again) 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 Swift going full-blown pop-punk (with bonus fiddle): “I’m dying to know / Is it killing you like it’s killing me?” The second the world gets back to normal, I’m going to the nearest karaoke room and belting “The Story Of Us” at the top of my lungs.
1. “All Too Well”
As with all song rankings, it’s tempting to be a contrarian at the top, to go against the near-unanimous consensus for an artist’s crowning achievement. Nah: “All Too Well” is the best Taylor Swift song. It’s also my favorite song by any artist ever, one that I wear like a scarf wrapped around my neck (as long as I don’t leave it at Maggie Gyllenhaal’s house). I write a line from the powerful bridge — “Running scared, I was there, I remember it all too well” — on my arm in Sharpie every time I run a race, as I’m too scared to get an actual tattoo, and if I had to pick my single favorite Swift lyric, it would be, “And you call me up again just to break me like a promise / So casually cruel in the name of being honest.” “All Too Well” is the song that I want to send to people who are interested in taking a deeper dive into Swift’s discography outside of the hits, but I’m always hesitant to do so, because I’m afraid our friendship would curdle if they didn’t like it.
It’s also an emotionally exhausting experience, so Swift rarely breaks it out in concert anymore (only 96 times since 2013; for the sake of comparison, she’s played another song from Red, “We Are Never Ever Getting Back Together,” 218 times in that same time period). But during the Reputation tour, she talked about the song’s unexpected impact:
“I feel like this song has two lives to it in my brain. In my brain, there’s the life of this song where this song was born out of catharsis and venting and trying to get over something and trying to understand it and process it. And then there’s the life where it went out into the world and you turned this song into something completely different for me. You turned this song into a collage of memories of watching you scream the words to this song, or seeing pictures that you post to me of you having written the words to this song in your diary, or you showing me your wrist, and you have a tattoo of the lyrics to this song underneath your skin. And that is how you have changed the song ‘All Too Well’ for me”
“All Too Well,” which was originally 10 minutes long (it’s 5:28 on the album) and written on a day when Swift was “just, like, a broken human, walking into rehearsal just 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 a masterpiece “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 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 single best song, one that everyone who hears it will remember all too well.