All 214 Taylor Swift Songs:
214. “Me!,” Lover (2019)
Most Swift songs grow with each listen. “Me!” is the exception: The more you hear it, the worse it sucks. After the Sturm und Drang of the Reputation era, “Me!” was a return to bubblegum pop, a mission statement that says “I’m through making mission statements.” While self-awareness may be Swift’s superpower, it fails her here. The attempt to reclaim a sense of youthful innocence works only by stripping out anything else that’s interesting or pleasurable about the music. Indeed, there’s something patronizing about kicking off an album full of gems like “Cornelia Street” and “Cruel Summer” with a song that makes Kidz Bop sound like In Our Time. She was seven years past “All Too Well” at this point, long enough to put away the baby food.
213. “Christmas Must Mean Something More,” The Taylor Swift Holiday Collection (2007)
One of two originals on Swift’s early-career Christmas album, “Something More” is a plea to put the Christ back in Christmas. Or as she puts it: “What if happiness came in a cardboard box? / Then I think there is something we all forgot.” In the future, Swift would get better at holding onto some empathy when she was casting a critical eye at the silly things people care about; here, the vibe is judgmental in a way that will be familiar to anyone who’s ever reread their teenage diary.
212. “Better Than Revenge,” Speak Now (2010)
A nasty little song that has not aged well. Whether a straightforward imitation of Avril Lavigne’s style or an early attempt at “Blank Space”–style self-satirization, the barbs never go beyond bratty. (As in “Look What You Made Me Do,” the revenge turns out to be the song itself, which feels hollow.) Best known now for the line about “the things she does on the mattress,” which I suspect has been cited in blog posts more times than the song was ever listened to, and has now been excised from the re-recording.
211. “Look What You Made Me Do,” Reputation (2017)
“There’s a mistake that I see artists make when they’re on their fourth or fifth record, and they think innovation is more important than solid songwriting,” Swift told New York back in 2013. “The most terrible letdown as a listener for me is when I’m listening to a song and I see what they were trying to do.” To Swift’s credit, it took her six records to get to this point. On a conceptual level, the mission here is clear: After the Kim-Kanye feud made her the thinking person’s least-favorite pop star, this comeback single would be her grand heel turn. But the villain costume sits uneasily on Swift’s shoulders, and even worse, the songwriting just isn’t there. The verses are vacuous, the insults have no teeth, and just when the whole thing seems to be leading up to a gigantic redemptive chorus, suddenly pop! The air goes out of it and we’re left with a taunting Right Said Fred reference — the musical equivalent of pulling a Looney Tunes gag on the listener. (I do dig the gleeful “Cuz she’s dead!” though.)
210. “Only the Young,” Miss Americana (2020)
While it’s understandable to wish Swift would have done more during the 2016 election, the effort to affix some blame to her for Hillary Clinton’s defeat rests on flimsy foundations. The Clinton campaign was hardly lacking for celebrity endorsem*nts, and as Swift herself has pointed out, at that moment she was as hated as she’d ever been. Any attempt to link her brand with Clinton’s likely would have rebounded to the detriment of them both. Nevertheless, whether in response to this backlash or simply to the obvious, Swift got more comfortable wading into the partisan arena during the Trump era, an evolution that takes center stage in her 2020 documentary, Miss Americana. This was an admirable thing to do, even if it hasn’t always resulted in good music. As the doc’s closing number makes clear, politics remains an awkward fit creatively. Swift isn’t a natural polemicist, straining her way through clunky couplets about the “big bad man” and his “big bad clan.” Docked at least a dozen spots for the verse about school shootings, the most cringeworthy of Swift’s recent output.
209. “Invisible,” Taylor Swift: Special Edition (2006)
A bonus track from the debut that plays like a proto–”You Belong With Me.” The “show you” / “know you” rhymes mark this as an early effort.
208. “You Need to Calm Down,” Lover (2019)
Unable to express themselves openly in popular art, the queer community historically has needed to operate through secret code. Since this is also Swift’s preferred method of communicating with superfans, it should come as no surprise that many of them thus convinced themselves the singer was implanting in her lyrics and music videos veiled references to her own Sapphic desires. Like ancient Christians expecting the imminent arrival of the Kingdom of God, the Gaylors may be destined never to experience the glorious day they’ve been waiting for, though they have the cold comfort of this Lover single, where Swift came out as an LGBTQ ally and buried the hatchet with Katy Perry, all at the same time. Besides being politically incoherent — was Tweeting at 7 a.m. really the thing that was bad about Donald Trump? — its slangy jabs felt dated even at the moment of release, as did the slight West Indian accents in the chorus. Coming hot on the heels of “Me!” this track did not get the Lover era off to the strongest of starts. As with Reputation, the real gems would emerge on the album proper.
207. “Crazier,” Hannah Montana: The Movie soundtrack (2009)
When approached by the filmmakers about contributing a song to the Hannah Montana movie, Swift sent in this track, seemingly a holdover from the Fearless sessions. In an admirable bit of dedication, she also showed up to play it in the film’s climax. It’s kind of a snooze.
206. “Change,” Fearless (2008)
A bit of paint-by-numbers inspiration that apparently did its job of spurring the 2008 U.S. Olympic team to greatness. They won 36 gold medals!
205. “A Place in This World,” Taylor Swift (2006)
Swift’s version of “Not a Girl, Not Yet a Woman,” this one feels like it missed its chance to be the theme tune for an ABC Family show.
204. “SuperStar,” Fearless: Platinum Edition (2008)
This bonus track is a relic of an unfamiliar time when Swift could conceivably be the less-famous person in a relationship.
203. “Beautiful Ghosts,” Cats soundtrack (2019)
Swift’s first foray into musical-theater writing is less embarrassing than the movie but still far too self-pitying to sit through more than once. Ever the dutiful student, Swift follows all the parameters of the assignment, yet moves like rhyming wanted with wanted come off as rookie mistakes.
202. “We Were Happy,” Fearless (Taylor’s Version) (2021)
There’s a thin line between timeless and basic, and this “from the vault” track stays on the wrong side.
201. “Highway Don’t Care,” Tim McGraw’s Two Lanes of Freedom (2013)
After joining Big Machine, McGraw gave Swift an “and” credit here as a professional courtesy. Though her backing vocals are very pleasant, this is 100 percent a Tim McGraw song.
200. “Don’t You,” Fearless (Taylor’s Version) (2021)
A mid-tempo breakup song from the vault that never achieves liftoff, though Jack Antonoff’s production at least gives it an alluring shape.
199. “A Perfectly Good Heart,” Taylor Swift: Special Edition (2006)
A pleading breakup song with one killer turn of phrase and not much else.
198. “Better Man,” Red (Taylor’s Version) (2021)
Swift’s vault tracks often feel like drafts for ideas that would be more fully sketched out in her official tracks — and never more so than on this one, whose opening notes are reminiscent of the beginning of “I Almost Do.”
197. “Cold As You,” Taylor Swift (2006)
A dead-serious breakup song that proved the teenage Swift could produce barbs sharper than most adults: “You come away with a great little story / Of a mess of a dreamer with the nerve to adore you.” Jesus.
196. “The Outside,” Taylor Swift (2006)
If you thought you felt weird judging songs by a high-schooler, here’s one by an actual sixth-grader. “The Outside” was the second song Swift ever wrote, and though the lyrics edge into self-pity at times, this is still probably the best song written by a 12-year-old since Mozart’s “Symphony No. 7 in D Major.”
195. “Dear Reader,” Midnights (3am Edition) (2022)
An ambient vibe that floats around without ever achieving much.
194. “That’s When,” Fearless (Taylor’s Version) (2021)
Another vault track that bears some vestigial similarities with a more famous Swift song, in this case, “You Belong With Me.” Keith Urban shows up to add a bit of country verisimilitude but not much interest.
193. “The Last Time,” Red (2012)
Red is Swift’s strongest album, but it suffers a bit from pacing issues: The back half is full of interminable ballads that you’ve got to slog through to get to the end. Worst of all is this duet with po-faced Ulsterman Gary Lightbody, which feels about ten minutes long.
192. “Superman,” Speak Now: Deluxe Edition (2010)
A bonus track that’s not gonna make anyone forget Five for Fighting any time soon. But I heard it playing in an airport a few years back, and it was better than I remembered.
191. “Sad Beautiful Tragic,” Red (2012)
Another glacially paced song from the back half of Red that somehow pulls off rhyming “magic” with “tragic.”
190. “Beautiful Eyes,” Beautiful Eyes EP (2008)
The title track of Swift’s early-career EP finds the young songwriter getting a lot of mileage out of one single vowel sound: Besides the eyes of the title, we’ve got I, why, fly, cry, lullaby, even sometimes. A spirited vocal performance in the outro saves the song from feeling like homework.
189. “The Lucky One,” Red (2012)
A plight-of-fame ballad from the back half of Red, with details that never rise above cliché and a melody that borrows from the one Swift cooked up for “Untouchable.”
188. “Glitch,” Midnights (3am Edition) (2022)
The most interesting things here are all in the background: the backing oohs, the noodly bass. The guitar sounds like late-period Graham Coxon.
187. “End Game,” Reputation (2017)
Swift’s embrace of a harder sound on Reputation led her to try her hand at rapping, most notably on this single, which sees her employ an awkward blaccent. Future and Ed Sheeran show up to form a Megazord of soulless late-’10s pop.
186. “Eyes Open,” The Hunger Games: Songs From District 12 and Beyond (2012)
One of two songs Swift contributed to the first Hunger Games soundtrack. With guitars seemingly ripped straight out of 1998 alt-rock radio, this one’s most interesting now as a preview of Swift’s Red sound.
185. “Tied Together With a Smile,” Taylor Swift (2006)
When she was just a teenager with a development deal, Swift hooked up with veteran Nashville songwriter Liz Rose. The two would collaborate on much of Swift’s first two albums. “We wrote and figured out that it really worked. She figured out she could write Taylor Swift songs, and I wouldn’t get in the way,” Rose said later. “She’d say a line and I’d say, ‘What if we say it like this?’ It’s kind of like editing.” This early ballad about a friend with bulimia sees Swift and Rose experimenting with metaphor. Most of them work.
184. “Babe,” Red (Taylor’s Version) (2021)
Sara Bareilles–core.
183. “Innocent,” Speak Now (2010)
The disparate reactions to Kanye West stage-crashing Swift at the 2009 VMAs speaks to the Rorschachian nature of Swift’s star image. Was Swift a teenage girl whose moment was ruined by an older man who couldn’t control himself? Or was she a white woman playing the victim to demonize an outspoken black man? Both are correct, which is why everyone’s spent so much time arguing about it. Unfortunately, Swift did herself no favors when she premiered “Innocent” at the next year’s VMAs, opening with footage of the incident, which couldn’t help but feel like she was milking it. (Fairly or not, the comparison to West’s own artistic response hardly earns any points in the song’s favor.) Stripped of all this context, “Innocent” is fine: Swift turns in a tender vocal performance, though the lyrics could stand to be less patronizing.
182. “Girl at Home,” Red: Deluxe Edition (2012)
This Red bonus track offers a foreshadowing of Swift’s interest in sparkly ’80s-style production. A singsongy melody accompanies a largely forgettable lyric, except for one hilariously blunt line: “It would be a fine proposition … if I was a stupid girl.”
181. “Mary’s Song (Oh My Oh My),” Taylor Swift (2006)
This early track was inspired by Swift’s elderly neighbors. Like “Starlight,” it’s a young person’s vision of lifelong love, skipping straight from proposal to old age.
180. “Come Back … Be Here,” Red: Deluxe Edition (2012)
A vulnerable track about long-distance love, with simple sentiments overwhelmed by extravagant production.
179. “Starlight,” Red (2012)
Never forget that one of the most critically acclaimed albums of the 2010s contains a piece of Ethel Kennedy fanfiction. The real story of Bobby and Ethel has more rough spots than you’ll find in this resolutely rose-colored track, but that’s what happens when you spend a summer hanging in Hyannis Port.
178. “Dancing With Our Hands Tied,” Reputation (2017)
Reputation sags a bit in the middle, never more than on this forgettable ’80s-inspired track.
177. “The Lakes,” Folklore (deluxe edition) (2020)
An attempt at channeling the naturalistic imagery of the Lake Poets winds up overwrought and overwritten. Though I do smile at the Wordsworth pun. (And yeah, sorry, I’m not gonna do the lowercase thing for the Folklore tracks.)
176. “Stay Stay Stay,” Red (2012)
Swift broke out her southern accent one last time for this attempt at homespun folk, which is marred by production that’s so clean it’s practically antiseptic. In an alternate universe where a less-ambitious Swift took a 9-to-5 job writing ad jingles, this one soundtracked a TV spot for the new AT&T family plan. In ours, it’s her “Ob La Di, Ob La Da.”
175. “High Infidelity,” Midnights (3am Edition) (2022)
Once freed from the expectation that everything was autobiography, Swift began to dive into the heads of straying partners. This one has an intriguing line about April 29 that invites a lot of speculation from gossip-minded listeners, but it pales next to similar efforts on Folklore and Evermore.
174. “I Don’t Wanna Live Forever,” Fifty Shades Darker soundtrack (2017)
In Fifty Shades Darker, this wan duet soundtracks a scene where Christian Grey and Anastasia Steele go for a sunny boat ride while wearing fabulous sweaters. On brand!
173. “No Body, No Crime,” Evermore (2020)
How far has Swift come from her Nashville days? So far that this country-tinged murder tale with the Haim sisters can’t help feeling more like a musical costume party than a genuine attempt at embodying darkness.
172. “Come in With the Rain,” Fearless: Platinum Edition (2008)
An ode to a long-lost lover that follows the Swift template a tad too slavishly.
171. “I Wish You Would,” 1989 (2014)
Like “You Are in Love,” this one originated as a Jack Antonoff instrumental track, and the finished version retains his fingerprints. Perhaps too much — you get the sense it might work better as a Bleachers song.
170. “I Heart ?,” Beautiful Eyes EP (2008)
Swift code-switches like a champ on this charmingly shallow country song, which comes from the Walmart-exclusive EP she released between her first two albums. Her vocals get pretty rough in the chorus, but at least we’re left with the delightful line, “Wake up and smell the breakup.”
169. “Paris,” Midnights (3am Edition) (2022)
Not actually about Paris, which spared Swift getting the Emily Cooper treatment from angry French people. I don’t think she needed to explain which kind of “shade” she meant. We all got it.
168. “Death by a Thousand Cuts,” Lover (2019)
Apparently inspired by a Netflix rom-com, and that tells you everything you need to know.
167. “The Great War,” Midnights (3am Edition) (2022)
Is it disrespectful to the generation of young men who perished at the Somme to use their deaths as a metaphor for an argument with Joe Alwyn? After 100 years, I say it’s fine.
166. “It’s Time to Go,” Evermore (physical edition) (2020)
Another “post-breakup catharsis” song, seemingly left off Evermore in favor of “Happiness.” The lyrics are about a romantic separation, but subtextually there are references to the Big Machine split, particularly when a banjo shows up.
165. “You’re Not Sorry,” Fearless (2008)
An unflinching kiss-off song that got a gothic remix for Swift’s appearance as an ill-fated teen on CSI. It shouldn’t work but it does, somewhat.
164. “I Think He Knows,” Lover (2019)
Not, as the title might imply, a slinky cheating ballad. Instead, it’s a straightforward love song. The stripped-down production in the verses makes a fun contrast with the bubbly chorus, but otherwise there’s not much here.
163. “Welcome to New York,” 1989 (2014)
In retrospect, there could not have been a song more perfectly designed to tick off the authenticity police — didn’t Swift know that real New Yorkers stayed up till 3 a.m. doing drugs with Fabrizio Moretti in the bathroom of Mars Bar? I hope you’re sitting down when I tell you this, but it’s possible the initial response to a Taylor Swift song might have been a little reactionary. When it’s not taken as a mission statement, “Welcome to New York” is totally tolerable, a glimmering confetti throwaway with lovely synths.
162. “Stay Beautiful,” Taylor Swift (2006)
Nathan Chapman was a Nashville session guitarist before he started working with Swift. He produced her early demos, and she fought for him to sit behind the controls on her debut; the two would work together on every Swift album until 1989, when his role was largely taken over by Max Martin and Shellback. Here, he brings a sprightly arrangement to Swift’s ode to an achingly good-looking man.
161. “Bye Bye Baby,” Fearless (Taylor’s Version) (2021)
The best part of this one is its big honkin’ hook that would have fit perfectly on country radio or maybe even Grey’s Anatomy.
160. “Vigilante sh*t,” Midnights (2022)
I don’t know if I buy the theory that Midnights is a collection of old songs that were gathering dust in Swift’s desk drawer, but I absolutely do believe this one is a Reputation holdover.
159. “Suburban Legends,” 1989 (Taylor’s Version) (2023)
One good line here: “flush with the currency of cool.”
158. “Christmas Tree Farm,” non-album single (2019)
The fake-out here makes me smile: She goes winter-jazzy in the intro, then hustles backstage to throw on some Mariah Carey drag. Swift says she wrote it in a weekend, and it definitely feels like a lark, something she tossed off not because she dreamed of knocking Burl Ives off the charts, but simply because she thought it’d be fun.
157. “So It Goes,” Reputation (2017)
Unfortunately not a Nick Lowe cover, this one comes and goes without making much of an impact, but if you don’t love that whispered “1-2-3,” I don’t know what to tell you.
156. “The Other Side of the Door,” Fearless: Platinum Edition (2008)
A bonus track saved from mediocrity by a gutsy outro that hints that Swift, like any good millennial, was a big fan of “Semi-Charmed Life.”
155. “Message in a Bottle,” Red (Taylor’s Version) (2021)
I worked at an American Eagle in the summer of 2006, and I swear they played this song on the speakers.
154. “Coney Island,” Evermore (2020)
One of the few bad things you can say about Swift’s quarantine reinvention is that it exacerbated her penchant for glum duets with dad rockers. After getting the National’s Aaron Dessner to produce much of Folklore and Evermore, Swift teamed up with the whole band for this track, which feels so heavy and middle-aged you’d swear it was interviewed for Meet Me in the Bathroom. She blends in all too well: Which one is the featured artist, again?
153. “Untouchable,” Fearless: Platinum Edition (2008)
Technically a Luna Halo cover (don’t worry about it), though Swift discards everything but the bones of the original. Her subsequent renovation job is worthy of HGTV: It’s nearly impossible to believe this was ever not a Taylor Swift song.
152. “Haunted,” Speak Now (2010)
In which Swift tries her hand at Evanescence-style goth-rock. She almost pulls it off, but at this point in Swift’s career her voice wasn’t quite strong enough to give the unrestrained performance the song calls for.
151. “Breathe,” Fearless (2008)
A Colbie Caillat collaboration that’s remarkable mostly for being a rare Swift song about a friend breakup. It’s like if “Bad Blood” contained actual human emotions.
150. “Mr. Perfectly Fine,” Fearless (Taylor’s Version) (2021)
A clever vault track with a lyrical Easter egg: Swift’s first use of the phrase “casually cruel,” four years before “All Too Well.”
149. “Last Kiss,” Speak Now (2010)
A good-bye waltz with an understated arrangement that suits the starkness of the lyrics.
148. “Right Where You Left Me,” Evermore (physical edition) (2020)
Miss Havisham cosplay, as Swift sings from the perspective of a woman who’s been frozen at the time and place she got dumped. In the documentary Miss Americana, Swift spoke about how celebrities are often mentally stuck at the age they were when they got famous, something she struggled with as she approached 30, but the metaphor is overwhelmed by the song’s Gothic elements.
147. “ False God ,” Lover (2019)
A woozy R&B track livened up by an undaunted vocal performance and a saxophonist really making the most of their time in the spotlight.
146. “This Love,” 1989 (2014)
Began life as a poem before evolving into an atmospheric 1989 deep cut. Like an imperfectly poached egg, it’s shapeless but still quite appetizing.
145. “The Best Day,” Fearless (2008)
Swift’s parents moved the family to Tennessee so she could follow her musical dreams, and she paid them back with this tender tribute. Mom gets the verses while Dad is relegated to the middle eight — even in song, the Mother’s Day–Father’s Day disparity holds up.
144. “If This Was a Movie,” Speak Now: Deluxe Edition (2010)
The mirror image of “White Horse,” which makes it feel oddly superfluous.
143. “Epiphany,” Folklore (2020)
When reaching for insight outside her own experience, Swift occasionally grasps for platitudes. In this ode to soldiers and frontline health-care workers we get both “just a flesh wound” and “someone’s daughter.” Credit to the singer for expanding outside her usual vocal range, though, deploying an Imogen Heap–style yawp on this one.
142. “Foolish One,” Speak Now (Taylor’s Version) (2023)
What do we want from a vault track? “Foolish One” has the advantage of sounding a lot like the other songs Swift was writing in the Speak Now era, rising climax and all. But apart from a stray use of delicate and a bridge that echoes the coda of “Enchanted,” little distinguishes this pleasant tale of romantic woe from its peers.
141. “…Ready for It?,” Reputation (2017)
I remember really hating this single and scoffing at Swift’s bars about Elizabeth Taylor and the flow she borrowed from Jay-Z. (Try to rap “Younger than my exes” without spilling into “Rest in peace, Bob Marley.”) But you can’t deny the chorus, a big Swift hook that sounds just like her best work — in this case because it bites heavily from “Wildest Dreams.”
140. “Daylight,” Lover (2019)
When it comes to ending an album on a note of catharsis and elemental imagery, I prefer “Clean.” And when it comes to employing this specific melody and cadence in a refrain, I prefer Beyoncé’s “Halo.” But I do love a good spoken-word mission statement!
139. “Wonderland,” 1989 (Deluxe Edition) (2014)
A deranged bonus track that sees Swift doing the absolute most. This song has everything: Alice in Wonderland metaphors, Rihanna chants, a zigzag bridge that recalls “I Knew You Were Trouble,” screams. As she puts it, “It’s all fun and games ’til somebody loses their MIND!”
138. “Tolerate It,” Evermore (2020)
Being happily coupled up did not diminish Swift’s ability to write heartbreaking songs about dying relationships; in this case, a study of a woman coming to grips with the fact that her partner has settled for her. Everything is off-balance, including the time signature, which is in 5/4. The cold, oppressive weight doesn’t lift until the bridge, when Swift leaps into her upper register to dream about getting the courage to break it off: “Believe me, I could do it.” But then the daydream ends, and we snap back to where we started. It’s clear she doesn’t quite believe it herself.
137. “Today Was a Fairytale,” Valentine’s Day soundtrack (2010)
How much of a roll was Swift on during the Fearless era? This song didn’t make the album, and sat in the vault for a year until Swift signed on for a small role in a Garry Marshall rom-com and offered it up for the soundtrack. Despite the extravagant title, the date described here is charmingly low-key: The dude wears a T-shirt, and his grand gestures are showing up on time and being nice.
136. “Hits Different,” Midnights (Deluxe Edition) (2022)
A once-elusive track that was available on the Target deluxe CD of Midnights. (It ?would later be added to the Til Dawn edition.) The title is a real “How do you do, fellow kids?” moment, but otherwise this is a pleasant break-up song enlivened by some weirdly specific lines about vomiting in the street. Compare the “ay-ee-ay” sound in the first line to that in “The Very First Night.”
135. “London Boy,” Lover (2019)
The song that gave the entire United Kingdom a chance to clown on Taylor Swift, which is the best gift the nation has received from an American since FDR’s Lend-Lease Act. British Twitter was particularly hung up on the fact that it’s impossible to visit every neighborhood she name-drops in one day … but nowhere in the song does Swift mention it’s supposed to be one day. It’s that kind of sloppiness that cost them the empire.
134. “The Very First Night,” Red (Taylor’s Version) (2021)
A vault track that sees Swift wishing she could “go back in time” to relive those heart-pounding early dates all over again. It’s not much on its own, but it does make you think about how these rerecordings let her go back in time, at least in a sense: She was an established grownup momentarily reliving the rushing passions of her youth. For a born memoirist like Swift, that must have been a dream come true.
133. “Sweeter Than Fiction,” One Chance soundtrack (2013)
Swift’s first collaboration with Jack Antonoff is appropriately ’80s-inspired, and so sugary that a well-placed key change in the chorus is the only thing that staves off a toothache.
132. “I’m Only Me When I’m With You,” Taylor Swift: Special Edition (2006)
A rollicking pop-rock tune that recalls early Kelly Clarkson. As if to reassure nervous country fans, the fiddle goes absolutely nuts.
131. “Tell Me Why,” Fearless (2008)
Another story of a lousy boyfriend, but it’s paired with one of Swift and Rose’s most winning melodies.
130. “The Man,” Lover (2019)
Beyoncé’s “If I Were a Boy” transported to the world of media meta-narratives. The chorus sums up so much you barely even need the rest. But it also feels more like a viral op-ed than a track that stands on its own.
129. “Ours,” Speak Now (Deluxe Edition) (2010)
It’s not this song’s fault that the extended version of Speak Now has songs called both “Mine” and “Ours” — and while “Ours” is good … well, it’s no “Mine.” Still, even if this song never rises above cuteness, it is incredibly cute. I think Dad’ll get over the tattoos.
128. “Bad Blood,” 1989 (2014)
As with “We Are Never Ever Getting Back Together,” “Bad Blood” represents a peak of Swift’s Max Martin era, when she was turning out perfectly crafted pop earworms that felt like they’d been designed in some subterranean Scandinavian laboratory. What she gained in hookiness, she lost in humanity. The schoolyard-chant melody here sounds like carved into a granite cliff face, 60 feet high. The lyrics indulges the worst habits of mid-period Swift — an eagerness to play the victim, a slight lack of resemblance to anything approaching real life. Still, “Bad Blood” is ranked this high in honor of its historical importance; its video is an artifact of the era when Swift was collecting famous friends like they were Pokémon. It’s not worth getting into the spat with Katy Perry that inspired the track, except to note that Swift’s assumption that she held the moral high ground in every celebrity feud would be the source of much trouble in the future.
127. “This Is Why We Can’t Have Nice Things,” Reputation (2017)
The first time I heard this, I thought it was one of the best things Swift had ever done — so much so that, at the moment she contemplates forgiving a hater, then bursts into an incredulous guffaw, I laughed out loud too. What can I say? It was late, and I was tired. I suspect Swift liked it just as much since she made it the epic finale for her Reputation live show. History hasn’t vindicated either of us, but the positive memories remain.
126. “Carolina,” Where the Crawdads Sing soundtrack (2022)
Swift had two shots at an Oscar nomination in 2022. The one she really wanted was a Best Live Action Short nod for her “All Too Well” video. (Which is … fine. If a film student turned it in you wouldn’t advise them to become a dentist, but you wouldn’t hand them an Oscar, either.) The other was Best Original Song for her closing-credits ballad from Where the Crawdads Sing, which is slightly less potent than earlier Southern Gothic efforts like “Seven,” but is still a million times better than the movie itself, which is fake, fake, fake. Unfortunately, Swift’s long wait for her first Oscar nom would continue. Original Song went to the exuberant “Naatu Naatu,” while the mawkish An Irish Goodbye won Live Action Short.
125. “Say Don’t Go,” 1989 (Taylor’s Version) (2023)
A vault track that sounds like she put all of 1989 in a blender and went BRRRRR. The preponderance of “say,” “stay,” and “go” in the lyrics points to a shared font of inspiration with “All You Had to Do Was Stay.”
124. “Happiness,” Evermore (2020)
A divorce ballad finished only a few days before Evermore’s release. Swift has written this type of cathartic breakup song before, and, attractive piano melody aside, not much separates this one.
123. “Snow on the Beach,” Midnights (2022)
When we heard Swift was collaborating with Lana Del Rey, fans expected a “Lady Marmalade”–level phenomenon. Instead, the original version of “Snow on the Beach” relegated Del Rey to a spectral presence in the distance. As a make-good, Swift reworked the song for the Til Dawn edition of Midnights, giving Lana a verse that adds some sorely needed dramatic heft. The title now reads, “feat. More Lana Del Rey,” which is hilarious.
122. “I Can See You,” Speak Now (Taylor’s Version) (2023)
Had this vault track been released in 2010, it would instantly have been the most adult song in Swift’s repertoire; the imagery is more sensual than anything she released before Red. Of course, had it come out in 2010, I don’t think it would have sounded much like the version we hear on the rerelease, which has an ’80s sharpness Swift wouldn’t add to her sound until years later.
121. “Labyrinth,” Midnights (2022)
Pitch-shifted vocals are to Midnights what cheerleader choruses were to Lover.
120. “Don’t Blame Me,” Reputation (2017)
A woozy if slightly anonymous love song that comes off as a sexier “Take Me to Church.” [A dozen Hozier fans storm out of the room.]
119. “Castles Crumbling,” Speak Now (Taylor’s Version) (2023)
Even as a pop prodigy who had experienced nothing but an unbroken string of successes, Swift was obsessed with her own inevitable downfall. That’s why she worked so hard to remain at the top, and why her 2016 cancellation amid the Kanye West/”Famous” fracas affected her as intensely as it did: Like a figure from a Greek tragedy, she saw it coming yet was unable to prevent it. This vault track continues the gothic strain that crept into Swift’s work around Speak Now, with special guest Hayley Williams adding a fitting level of melodrama. She would later repurpose the title phrase for the opening line of 2017’s “Call It What You Want.”
118. “Closure,” Evermore (2020)
“Closure” features one of the bigger production swings of Swift’s quarantine era, an industrial drum track that sparks up a song that otherwise remains subdued. (I’ve seen the percussion compared to Nine Inch Nails, but the Postal Service feels more her wavelength.) It works better than Swift’s other capital-C choice: her decision to sing the chorus in a British accent. You wot?
117. “Exile,” Folklore (2020)
The first sign that Folklore would not be an album you put on in the background while doing something else, this plodding Bon Iver duet broke my patience a few times. Only when I got my headphones and really listened to it did I pick up the jagged edges in the breakup ballad. “I can see you staring, honey / Like he’s just your understudy” is an underrated blood-drawer. Rest in peace to co-writer “William Bowery,” who will probably never be heard from again.
116. “‘slu*t!,’” 1989 (Taylor’s Version) (2023)
The title is a little misleading: This is not a hater-baiting anthem, but rather a dreamy ballad exalting in the feeling of dating a man everyone else covets. Docked five spots for biting “drunk in love.”
115. “Electric Touch,” Speak Now (Taylor’s Version) (2023)
Swift has a built-in ability to take in everything she sees. To commemorate Fall Out Boy’s influence on her Speak Now–era songwriting, she brought the band in to collaborate on this vault track. Together they do a more than capable version of FOB’s big rock sound with Swift singing the hell out of that huge, anthemic hook.
114. “Paper Rings,” Lover (2019)
Had Swift never moved to Nashville, this pop-punk confection sounds like something she might have released in the late aughts. I know some fans think it’s silly, but they played it at my brother’s wedding so I couldn’t possibly dislike it.
113. “I Bet You Think About Me,” Red (Taylor’s Version) (2021)
This duet with Chris Stapleton is another acid-penned kiss-off to a Jake Gyllenhaal type. All in good fun, though she lays on the reverse-snobbery a bit thick in lines like “I was raised on a farm; no, it wasn’t a mansion.” Girl, your dad worked for Merrill Lynch.
112. “You All Over Me,” Fearless (Taylor’s Version) (2021)
The best vault track from the Fearless rerelease, written all the way back in 2005 and given a tasteful country sheen with the help of Maren Morris’s backup vocals. It’s additional proof that, even as a high-schooler, she had the lyrical skills of a seasoned professional, displaying a deft hand at metaphor here. One has to wonder if the reason it was never released is that, given Swift’s squeaky-clean image at the time, the chorus was ripe for misinterpretation.
111. “Question…?,” Midnights (2022)
A trip down memory lane to the 1989 era — literally, in the case of the “Out of the Woods” interpolation but also in the vibes and lyrical callbacks. I like that she adds her friends’ cheers into the chorus the second time around.
110. “How You Get the Girl,” 1989 (2014)
The breeziest and least complicated of Swift’s guy-standing-on-a-doorstep songs, which contributed to the feeling that 1989 was something of an emotional regression. You probably shouldn’t take it as an instruction manual unless you’re Harry Styles.
109. “Timeless,” Speak Now (Taylor’s Version) (2023)
Young Swift enjoyed imagining the inner lives of older couples she idealized. This one’s about her grandparents, Marjorie and Robert. While songs like “Starlight” spin off quickly into fantasy, the personal connection here grounds “Timeless” in something approaching real life.
108. “Mirrorball,” Folklore (2020)
This reverb-drenched track has garnered comparisons to the Sundays and Sixpence None the Richer, and the ’90s pastiche is spot-on, though unfortunately a tad sleepier than its forebears. Question for the group: Did she get the title from Sarah McLachlan or Everything But the Girl?
107. “I Know Places,” 1989 (2014)
No attempts of universality here — this trip-hop song about trying to find a place to make out when you’re a massive celebrity is only relatable to a couple dozen people. No matter. As a slice of gothic pop-star paranoia, it gives a much-needed bit of edge to 1989. Bumped up a couple of spots for the line about vultures, which I can only assume is a shout-out.
106. “This Is Me Trying,” Folklore (2020)
Do you need subtext? This unguarded track surfs along with its heart on its sleeve, plus a languid saxophone and a few great turns of phrase. (“I got wasted like all my potential.”) The climax sneaks up on you like a moment of clarity.
105. “Forever Winter,” Red (Taylor’s Version) (2021)
This is widely assumed to be a memorial for a high-school friend who died too young. Grief is the animating emotion behind many of Swift’s best songs, and faced with a different type of loss than the one she usually writes about, her emotions ring true.
104. “The Way I Loved You,” Fearless (2008)
Written in collaboration with Big and Rich’s John Rich, which may explain how stately and mid-tempo this one is. (There’s even a martial drumbeat.) Here, she’s faced with a choice between a too-perfect guy — he’s close to her mother and talks business with her father — and a tempestuous relationship full of “screaming and fighting and kissing in the rain,” and if you don’t know which one she prefers I suggest you listen to more Taylor Swift songs. Swift often plays guessing games about which parts of her songs are autobiographical, but this one is explicitly a fantasy.
103. “Sparks Fly,” Speak Now (2010)
This one dates back to Swift’s high-school days and was destined for obscurity until fans fell in love with the live version. After what seems like a lot of tinkering, “Sparks Fly” finally got a proper studio release on Swift’s third album. Because of this, Swifties treasure it dearly, but I prefer her other “kissing in the rain” songs.
102. “Bigger Than the Whole Sky,” Midnights (3am Edition) (2022)
Borrowing a phrase from Emily Dickinson, Swift mourns a lost relationship (maybe a breakup, a death, or possibly a miscarriage.) It’s sparse, but her vulnerable vocals sell it.
101. “Cowboy Like Me,” Evermore (2020)
Had Swift lacked the charisma to become a star herself, I like to think she would’ve become one of those Nashville jobbers who lurks behind the scenes writing radio hits for other artists. This twangy ballad about con artists who fall in love feels like the work of that alternate-reality Swift. Fortunately, the lived-in cynicism of the lyrics belies the tune’s anonymous qualities.
100. “It’s Nice to Have a Friend,” Lover (2019)
Much of the pleasure here comes via a sample from a Toronto music academy, a steel-drum-and-chorus beat that sounds like nothing else in Swift’s discography. The schoolyard vibe fits the playground-romance lyrics; I assume any resemblance to the plot of Carol is accidental.
99. “Christmases When You Were Mine,” The Taylor Swift Holiday Collection (2007)
The clear standout of Swift’s Christmas album, with an endearingly winsome riff and lyrics that paint a poignant picture of yuletide heartbreak. If you’ve ever been alone on Christmas, this is your song.
98. “The 1,” Folklore (2020)
An easy, breezy intro destined to end up in Spotify’s Favorite Coffeehouse playlist.
97. “Miss Americana & the Heartbreak Prince,” Lover (2019)
After years of being dinged for staying apolitical in her art, Swift takes her first step into the arena here, reframing the 2016 election through the high-school environment that provided so much of her early inspiration. It’s an ambitious conceit that I don’t think works 100 percent, but I appreciate the big swing. Knocked a few spots for featuring the cheerleader chorus on Lover that finally broke me.
96. “Should’ve Said No,” Taylor Swift (2006)
Written in a rush of emotion near the end of recording for the debut, what this early single lacks in nuance it makes up for in backbone. I appreciate the way the end of each verse holds out hope for the cheating ex — “given ooonnne chaaance, it was a moment of weeaaknesssss” — before the chorus slams the door in the dumb lunk’s face.
95. “Run,” Red (Taylor’s Version) (2021)
A slight duet with Ed Sheeran that finds them both running on autopilot through some perfectly pleasant territory. That she could afford to keep a song like this in the vault says something about the quality of work she was turning out during the Red era.
94. “You’re Losing Me,” Midnights (2023)
An ultra-rarity — only available to those who attended Swift’s Eras Tour stop in New Jersey — which develops the medical metaphor first employed on Folklore’s “Epiphany.” Here she compares the slow death of a relationship to a patient losing consciousness, a successful addition to Midnight’s bevy of self-loving/self-hating recriminations. Also bears the distinction of possibly being the first song of the post-Alwyn era, as the line “I wouldn’t marry me either” was an irresistible hint for the gossip-hounds.
93. “New Romantics,” 1989 (Deluxe Edition) (2014)
Like “22,” an attempt at writing a big generational anthem. Being left off the album proper suggests Swift didn’t think it quite got there, though it did its job of extending the singles cycle of 1989 a few more months. Despite what anyone says about “Welcome to New York,” the line here about waiting for “trains that just aren’t coming” indicates its writer has had at least one authentic New York experience.
92. “Gold Rush,” Evermore (2020)
What initially seems like another ode to Alwyn reveals itself, Owl Creek Bridge–style, to actually be the fantasy of an unlucky-in-love narrator. The throbbing chorus doesn’t really do it for me, but I appreciate the swooning imagery in the verses, as visions of dinner parties and vacations fade away into “the gray of my day-old tea.” Bumped up a spot for the reminder that Swift is an Iggles fan.
91. “King of My Heart,” Reputation (2017)
It took me a while to warm up to Joe Alwyn as a muse. I just didn’t find the guy compelling, and I missed the dramatic sweep of Swift’s earlier romances. With a little distance, I see now that that was the point: The understated relationship depicted in Reputation and elsewhere was a respite from everything going on in Swift’s public life. When millions of listeners are convinced you’re a horrible person, finding one person who knows you’re not is a godsend. As the years went by, tracks like “Cornelia Street” gave the Alywn era its own lore, and when it ended, I was more broken up about it than I ever expected. But I still can’t really get into this one.
90. “You Are in Love,” 1989 (Deluxe Edition) (2014)
The best of Swift’s songs idealizing someone else’s love story (see “Starlight” and “Mary’s Song”), this bonus track sketches Jack Antonoff and Lena Dunham’s relationship in flashes of moments. The production and vocals are appropriately restrained — sometimes, simplicity works.
89. “Mastermind,” Midnights (2022)
I have trouble doing things with intention. I get nervous about choosing the wrong path, delay until it’s almost too late, and then make a haphazard decision at the last minute. One thing I admire about Swift is she does not appear to suffer from this problem. To close out Midnights, she eschews her typical quiet summation in favor of a joking-but-not-really examination of her obsession with control. “No one wanted to play with me as a little kid / So I’ve been scheming like a criminal ever since / To make them love me and make it seem effortless.” Is it parody masquerading as confession, or confession masquerading as parody? All I know is there are few moments on Midnights more cathartic than when the synths hit in the pre-chorus.
88. “Mad Woman,” Folklore (2020)
The notion of Folklore as Swift’s “goth album” didn’t extend much further than the promo imagery and this side-two spooker, a haunting evocation of female rage. It gives us the unrepentant knife-twisting that Reputation only gestured at, and it gets 13 percent more fun if you pretend she’s saying, “Mouth-f*ck you forever.”
87. “I Almost Do,” Red (2012)
The kind of plaintive breakup song Swift could write in her sleep at this point in her career, with standout guitar work and impressive vulnerability in both lyrics and performance.
86. “Evermore,” Evermore (2020)
Swift returns to the isolated woodland compound where she left Bon Iver after “Exile” and whaddya know, he still works! This one’s less turgid than its predecessor, and if the duo’s vocal parts feel uncomfortably stitched together at times, at least they come together for a rousing back-and-forth climax.
85. “Illicit Affairs,” Folklore (2020)
There’s more than a little Sufjan Stevens in the way Swift shoots up into falsetto at the end of each second line. “A dwindling mercurial HIGH!” Though this is one of the implicitly fictional songs on Folklore, it’s a signpost of Swift’s increasing comfort with playing the bad guy in romantic relationships.
84. “The Story of Us,” Speak Now (2010)
The deluxe edition of Speak Now features both U.S. and international versions of some of the singles, which gives you a sense of how fine-tuned Swift’s operation was by this point. My ears can’t quite hear the difference between the two versions of this exuberant breakup jam, but I suspect the U.S. mix contains some sort of ultrasonic frequencies designed to … sorry, I’ve already said too much.
83. “I Did Something Bad,” Reputation (2017)
Have you ever gone back and read any of those blog posts about Swift from 2016? People were zooming in on Notes App screenshots, searching for hidden pixels that supposedly proved her perfidious nature. Of course she went a little crazy and recorded a super-defensive album about it — anyone would! The best way to get a sense of Swift’s headspace in the months after her cancellation is to listen to this Reputation deep cut, which overflows with aggression and paranoia. Is that a raga chant? Are those f*cking gunshots? Docked a spot or ten for “They’re burning all the witches even if you aren’t one,” which doth protest too much, but bumped up just as much for Swift’s first on-the-record “sh*t.”
82. “Never Grow Up,” Speak Now (2010)
Swift’s songs where she’s romanticizing childhood come off better than the ones where she’s romanticizing old age. (Possibly because she’s been a child before.) This one is so well-observed and wistful about the idea of children aging that you’d swear she was secretly a 39-year-old mom.
81. “Now That We Don’t Talk,” 1989 (Taylor’s Version) (2023)
A popular conspiracy theory says the vault tracks on the Taylor’s Version releases aren’t actually as old as Swift claims. More evidence comes in this little sketch, the shortest song she’s ever put out, which is so bitingly specific you can’t believe it’s not about Jake Gyllenhaal. But if it is indeed about Harry Styles, then why is she referencing things that happened in 2018? Whenever they were written, the lyrics here are meaner than anything Swift was willing to say on the record about Styles in 2014, though you can tell they’re coming from a place of genuine hurt. The rising falsetto in the chorus should be trademarked at this point.
80. “White Horse,” Fearless (2008)
You’d never call Swift a genre deconstructionist, but her best work digs deeper into romantic tropes than she gets credit for. In just her second album, she and Rose gave us this clear-eyed look at the emptiness of symbolic gestures, allegedly finished in a mere 45 minutes. Almost left off the album, but saved thanks to Shonda Rhimes.
79. “Dorothea,” Evermore (2020)
Like “Betty” on Folklore, an effortless channeling of Swift’s old sound on a fictional tale of teenage romance. According to the author, “Dorothea” canonically takes place in the same universe as Folklore’s love-triangle trilogy, though the melodrama has been turned down a few notches. It’s a wistful recollection of the narrator’s high-school relationship with the title character, who skipped town, became a big star, and never looked back. The lyrics are folksy and self-effacing, as Swift dreams of a reunion while constantly reminding herself that it could never happen. But she can’t quite stop herself from holding out hope: “If you’re ever tired of b?ing known for who you know / You know that you’ll always know me.” The optimism might not be too misguided: According to “‘Tis the Damn Season,” these two haven’t seen the last of each other.
78. “All You Had to Do Was Stay,” 1989 (2014)
Just like the melody to “Yesterday” and the “Satisfaction” riff, the high-pitched “Stay!” here came to its writer in a dream. Inspiration works in mysterious ways.
77. “Call It What You Want,” Reputation (2017)
This airy slow jam about losing yourself in love following a scandal turns out surprisingly sexy, though the saltiness in the verses (“all the liars are calling me one”) occasionally betrays the sentiment.
76. “Teardrops on My Guitar,” Taylor Swift (2006)
A portrait of high-school heartbreak, equal parts mundane — no adult songwriter would have named the crush “Drew” — and melodramatic. It’s also the best example of Swift and Rose’s early songwriting cheat code, when they switch the words of the chorus around at the end of the song. “It just makes the listener feel like the writer and the artist care about the song,” Rose told Billboard. “That they’re like, “Okay, you’ve heard it, but wait a minute — ’cause I want you know that this really affected me, I’m gonna dig the knife in just a little bit deeper.’” (“Teardrops” ended up inspiring a moment that could have come straight out of a Taylor Swift song, when the real Drew showed up outside her house one night. “I hadn’t talked to him in two-and-a-half years,” she told the Washington Post. “He was like: ‘Hey, how’s it going?’ And I’m like: ‘Wow, you’re late? Good to see you?’”)
75. “Everything Has Changed,” Red (2012)
“We good to go?” For many American listeners, this was the first introduction to a redheaded crooner named Ed Sheeran. It’s a sweet duet and Sheeran’s got a roughness that goes well with Swift’s cleaner vocals, but the harmonies are a bit bland.
74. “You’re on Your Own, Kid,” Midnights (2022)
The millennial tendency to loudly decry a situation while obscuring one’s own agency: I have lost my patience for it. So I appreciate the honesty in this advice to younger listeners in which Swift reveals the secret trials of her 20-something superstardom — “I hosted parties and starved my body / Like I’d be saved by a perfect kiss” — but also notes, “I took the money.” The lesson that nothing is ever as good as it seems from the outside is hard-earned, even if the conclusion, to live in the moment, is a little pat.
73. “I Forgot That You Existed,” Lover (2019)
Probably too noncommittal to be a first single, but man, imagine how different the buzz for Lover would have been had this winning song been our introduction to the era. As it is, it’s a fitting leadoff track for the album proper, as Swift puts the Reputation drama behind her with a sprightly ode to the joy of indifference. In a fun twist, the utter lack of negative emotion here makes this one of Swift’s coldest kiss-off songs. Elie Wiesel was right.
72. “Clean,” 1989 (2014)
Co-written with Imogen Heap, who contributes backup vocals. This is 1989’s big end-of-album-catharsis song, and the water imagery of the lyrics goes well with the drip-drip-drip production. I’d be curious to hear a version where Heap sings lead; the minimalist sound might be better suited for her voice, which has a little more texture.
71. “Marjorie,” Evermore (2020)
In which an artist known for worldly concerns wades into the realm of the spiritual. The song’s addressed to Swift’s late grandmother Marjorie Finlay, an opera singer who passed away in 2003. But that doesn’t mean she’s gone, Swift says: “What died didn’t stay dead / You’re alive in my head.” In fact, she can hear her grandma singing to her right now, at which point we hear the real Marjorie crooning in the background — a conjuring both haunting and strangely comforting.
70. “Long Live (We Will Be Remembered),” Speak Now (2010)
Ostensibly written about Swift’s experiences touring with her band, but universal enough that it’s been taken as a graduation song by pretty much everyone else. Turns out, adolescent self-mythologizing is the same no matter where you are — no surprise that Swift could pull it off despite leaving school after sophom*ore year.
69. “Peace,” Folklore (2020)
The normal rules of Taylor Swift album sequencing say this lo-fi love song should have been the last track on Folklore, but I guess that’s 2020 for you. More clearly autobiographical than much of the album, Swift apologizes to her lover for the stress that comes with dating one of the world’s most famous women. There’s a world where that comes off as an insufferable flex, but her unassuming authenticity keeps it far away from humblebrag territory.
68. “Bejeweled,” Midnights (2022)
Workmanlike pop in the 1989 mode. Lyrically, this is kind of the same song as “Me!” but rewritten to be less annoying. Swift isn’t talking about how great she is just for the sake of it but to remind an inattentive partner what he’s taking for granted. Like the Beatles and diamond rings, precious gems are the luxe imagery she keeps close whenever she needs a metaphor.
67. “Long Story Short,” Evermore (2020)
Do you ever look back on a crisis that used to consume your entire life and find yourself shocked by how small it seems in retrospect? That’s where Swift’s at in this breezy electro-pop track, which sums up years of public drama with a terse, “Long story short, it was a bad time.” Reputation found Swift playing at being over it while clearly not being over it; here, the sentiment finally feels genuine. I think I speak for everyone, though, when I say we’d be fine with this being her final word on the subject.
66. “Jump Then Fall,” Fearless (Platinum Edition) (2006)
An effervescent banjo-driven love song. I get a silly kick out of the gag in the chorus, when Swift’s voice leaps to the top of her register every time she says “jump.”
65. “Soon You’ll Get Better,” Lover (2019)
Swift brought out the Dixie Chicks for this soft acoustic ballad inspired by her mother’s cancer recurrence. Despite the star-studded lineup, the song is simple, sincere, and affecting, and Swift’s vocals infuse the heartbreaking details with just the right amount of childish naivety: “You’ll get better soon / ’cause you have to.”
64. “Lavender Haze,” Midnights (2022)
Amid the generally positive reception for Midnights, some critics took issue with Swift’s falling back on the Antonoffian sound she developed on 1989 rather than continuing the experiments of her pandemic recordings. There’s no denying Midnights’ lyrics cut less deep, but it’s not a complete backslide: In tracks like this one, she navigates complicated emotional terrain, exploring the way the fame industry has no frame of reference for an unmarried, childless woman in a long-term relationship. “All they keep asking me is if I’m gonna be your bride,” she sings. “The only kinda girl they see is a one-night or a wife.” She’s had it with the “1950s sh*t they want from me,” but there’s a tiny part of her that sees the appeal: The title comes from a bit of ’50s slang she picked up from Mad Men.
63. “The Moment I Knew,” Red (Deluxe Edition) (2012)
An epic account of being stood up that makes a terrible birthday party seem like something approximating the Fall of Troy. If you’re the type of person who stays up at night remembering every inconsiderate thing you’ve ever done, the level of excruciating detail here is like a needle to the heart.
62. “Hoax,” Folklore (2020)
So intimate it’s almost uncomfortable: Just Swift, a piano, and quiet strings, bathed in religious imagery and nods to private tragedies we’ll probably never know about.
61. “Back to December,” Speak Now (2010)
At the time, this one was billed as a big step for Swift: the first song where she’s the bad guy! Now that the novelty has worn off “Back to December” doesn’t feel so groundbreaking, but it does show her evolving sensitivity. The key to a good apology has always been sincerity, and whatever faults Swift may have, a lack of sincerity has never been one of them.
60. “Nothing New,” Red (Taylor’s Version) (2021)
Swift hadn’t yet lived through a public-enemy cycle when she wrote this self-aware ballad in the spring of 2012, but she was perceptive enough to see what was coming: “Shoot you down, and then they sigh / And say, ‘She looks like she’s been through it.’” There’s a vulnerability here that presages her later songs, as 22-year-old Swift works through her anxiety about one day losing the currency of youth, wondering what it’ll be like when she’s the legacy act all the bright young things are name-dropping. The version she finally recorded proved it doesn’t have to be so sad: Nine years later, she was generous enough to share the mic with one of those acolytes, Phoebe Bridgers.
59. “Willow,” Evermore (2020)
Evermore kicks off with a visit to the world’s most melancholy coffeehouse. “Willow” is a love song, but it’s so prickly and suspicious it doesn’t always sound like one. There’s a striking sharpness to this track, both in the fingerpicked guitar line and in Swift’s plea for her man to “take my hand / wreck my plans.” Docked five spots for the “’90s trend” line, which feels like something she threw in because she wanted to put it on a T-shirt.
58. “My Tears Ricochet,” Folklore (2020)
Swift’s separation from her old label Big Machine gets a dramatic breakup anthem worthy of the years they spent together. She concocts a ghostly fantasy about watching your enemies wail at your funeral; the operatic grandeur of Antonoff’s production is only too apropos. Surely it’s a coincidence that the intro sounds a bit like a song from one of Swift’s other old enemies?
57. “Is It Over Now?,” 1989 (Taylor’s Version) (2023)
The Atlantic called 1989 Swift’s “Tinder record”: No other album of hers is as suggestive of late-night texts and strangers’ naked limbs. This vault track is the morning-after hangover, as Swift takes stock of a fling in which she was never sure where they stood, now that they’re both f*cking other people. From the complications that come from both parties being equally famous, to the lyrical Easter eggs about iconic paparazzi photos, and the overall sense of lying alone on the couch replaying everything in your head, this is classic Swift. The audible callbacks to “Out of the Woods” are the cherry on top: the same unsteady feeling from two points in the same relationship, one from the high, the other from the wreckage.
56. “When Emma Falls in Love,” Speak Now (Taylor’s Version) (2023)
Many fans believe this song is about Emma Stone, who befriended Swift around the same time the latter was working on Speak Now. Whether that’s true or not, this ballad is Swift at her most observant, an effortlessly poetic character study of a friend falling in love for the first time. Warning: From now on, any time an Emma gets married, you’re going to hear this song — probably for the rest of your life.
55. “Would’ve, Could’ve, Should’ve,” Midnights (3am Edition) (2022)
Alt-rock ’90s guitars soundtrack this scathing song about an older guy who may or may not have half a dozen Grammys. He was a “promising grown man”; she was a child he “got to wash [his] hands” of. This is Swift’s strongest vocal performance on Midnights, rising with the exhilaration of her “dance with the Devil” and breaking in anguish when she pleads, “Give me back my girlhood, it was mine first.” Your heart breaks with her.
54. “Holy Ground,” Red (2012)
This chugging rocker nails the feeling of reconnecting with
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