- Taylor Swift is a 10-time Grammy Award winning artist whose career spans 13 years and seven studio albums.
- Critics and fans alike believe she struck gold with emotional ballads like “All Too Well” and satirical pop songs like “Blank Space.”
- However, not every track in her discography is a gem. The upbeat, radio-friendly “ME!” is cloying and juvenile while the overproduced “Bad Blood” doesn’t deliver the punch it intended.
- Insider considered listenability, lyrical quality, production value, and critic reception to come up with the 15 best and 15 worst songs of the singer’s career thus far.
- Songs Swift has been featured in and songs produced for soundtracks were not factored into these rankings.
- Visit Insider’s homepage for more stories.
“All Too Well” has been hailed as Swift’s all-time best song by critics and fans alike.
What started off as a deep cut on “Red” swiftly became heralded as the singer’s magnum opus, and for good reason. It’s almost literary in how distinctively Swift tells her story of forgotten scarves, plaid shirt days, and the pain of remembering every excruciating detail of being in love after the magic’s not there no more.
“It’s full of killer moments: the way she sings ‘refrigerator,’ the way she spits out the consonants of ‘crumpled-up piece of paper,’ the way she chews up three ‘all’s in a row,'” Rob Sheffield wrote about the track for Rolling Stone. “No other song does such a stellar job of showing off her ability to blow up a trivial little detail into a legendary heartache.”
Song highlight: All of it.
If you like this, listen to: it on repeat.
“Dear John” is a master class in emotional breakup ballads.
Swift didn’t just wake up one day and write “All Too Well” without any prior songwriting experience and “Dear John” was solid practice in crafting a breakup ballad that cuts to the core. It gets even better when you realize the songstress wrote all six minutes and 43 seconds alone at the wise old age of 19.
The Hollywood Reporter dubbed “Dear John” the “best and most shocking song” on 2010’s “Speak Now” with Chris Willman writing that it’s “a brilliant song, and not necessarily an easy one to listen to… at least until the chills-inducing climax.”
Song highlight: “But I took your matches before fire could catch me / So don’t look now, I’m shining like fireworks over your sad, empty town.”
If you like this, listen to: “Last Kiss.”
“Style” is among the songs in Swift’s catalogue that will truly, as she sings, “never go out of style.”
“Style” as GQ’s Jay Willis puts it, is a “fatalistic, vaguely noir-ish account of young love in turmoil.”
Swift teamed up with pop-production masters Max Martin and Shellback to create this synth-pop masterpiece that is so rock-solid even Swift can’t keep herself from referencing it in later works. The opening phrase of the second verse, “So it goes,” became a track title on “Reputation,” while “take me home” was transformed from a cheeky nod toward One Direction’s sophomore album into a heartfelt plea to her beloved on 2019’s “Lover.”
At risk of sounding corny, “Style” really is one of the few pop songs this decade that didn’t (and won’t) go out of style.
Song highlight: The way that lyrics like “You’ve got that James Dean daydream look in your eye,” make the track feel like it was (allegedly) written about the cool, rocker Harry Styles that we know today, instead of the 18-year-old, baby-faced Styles that Swift dated in late 2012.
If you like this, listen to: “Cruel Summer.”
For a song about fearing you could never revisit home if a sacred relationship went wrong, “Cornelia Street” felt in a lot of ways like a homecoming for Swift.
Swift inserted plenty of callbacks to her previous works on “Lover,” but there was no song that felt most like the Old Taylor than “Cornelia Street.” From autumnal scenes to memories set in kitchens, there are plenty of parallels between this track and Swift’s magnum opus, “All Too Well.”
But while “All Too Well” is about a love forever lost, “Cornelia Street” is about a love Swift fears losing more than anything. It’s a beautiful culmination of her past work that shows just how far the singer has grown in her romantic life, while acknowledging the lessons of fragility she’s learned and that at any moment, everything she built could disappear.
Nevertheless, “Cornelia Street” is the kind of triumph in love that fans have waited 13 years to see.
Song highlight: The breathiness of how she sings, “And baby, I get mystified by how this city screams your name.”
If you like this, listen to: “New Year’s Day.”
“Teardrops on My Guitar” set the stage for Swift’s success and eventual pop takeover.
Swift found early success in her career with the second single off her debut album. “Teardrops on My Guitar” was a definitive country song that found its way onto the pop charts, foreshadowing Swift’s eventual full-time crossover to the genre.
“The ease with which ‘Teardrops’ translated to straight pop showed that her deft melodic touch and conversational way with deeply felt emotions could scale to the widest possible audience,” Maura Johnston wrote for Pitchfork. “Today, her production takes its cue from current trends, and her subjects don’t need to be identified via online fishing expeditions, but her detailed lyrics and canny worldview were there from the start.”
Song highlight: “So I’ll drive home alone / As I turn out the light / I’ll put his picture down / And maybe get some sleep tonight.”
If you like this, listen to: “Tim McGraw.”
“Lover” helped break Swift onto the wedding music scene for the first time.
Swift’s music has always been marked by its penchant for romance, which is why it’s surprising that it took seven albums for her to write a song that fits so at home at a wedding reception.
As Rolling Stone’s Rob Sheffield writes, “It’s the perfect autobiographical title song, for this most nakedly autobiographical of Swift albums.”
“Lover” in all of its waltzy, overdramatic glory is a timeless ode to finding your forever person that fans will likely only grow fonder of as years go by. It’s already one of Swift’s own personal favorites.
Song highlight: The bridge.
If you like this, listen to: “You Are in Love.”
“Enchanted” is a sparkling example of Swift’s uncanny ability to isolate a personal experience and make it feel universal.
“Enchanted” eloquently tells the story of meeting someone for the first time, and being so completely swept off your feet by their charm that you find yourself dancing around all alone at 2 a.m. reflecting on the brief exchange, hoping it turns into something more.
“The hazy crush of ‘Enchanted’ showcases Swift’s instinct for capturing emotion with astonishing exactitude — right down to the dread sneaking in at the song’s close,” Alex Macpherson wrote about the song for The Guardian.
Song highlight: “This night is sparkling, don’t you let it go / I’m wonderstruck, blushing all the way home.”
If you like this, listen to: “Treacherous.”
“I Knew You Were Trouble” is a Max Martin and Shellback collaboration that pushed Swift’s boundaries as a musician.
While 2012’s “Red” wasn’t a complete departure from country, Swift proved her interest in cross-genre experimentation with “I Knew You Were Trouble,” a pop-rock, dubstep-infused bop about getting involved with someone you suspect isn’t right for you from the start.
As Brad Nelson wrote for Pitchfork, “It was as if she had finally found a musical backdrop sharp as her lyrics — the lakes and backroads of Tennessee and Georgia disappear, replaced with formations of jagged crystal, a perfect environment for a song about falling in love with someone you know will hurt you and leave you feeling empty as a canyon.”
Song highlight: “Pretend he doesn’t know / That he’s the reason why / You’re drowning, you’re drowning, you’re drowning.”
If you like this, listen to: “Don’t Blame Me.”
The songwriting on “Clean” has been praised by critics for bringing “truth and power” to a modern pop song.
For those who stan a Swift closing number, “Clean” is the holy grail. It so succinctly sums up everything she had learned over the course of “1989” while simultaneously providing a glimmer of hope to its listeners that their storm too shall pass.
Neil McCormick called the track “understated” and “atmospheric” in a review of “1989” for The Telegraph, adding that “Clean” offers “a truth and power rare in commercialized pop.”
The Guardian’s Alexis Petridis praised the opening line, “The drought was the very worst,” for not only being a “striking line with which to open a pop song,” but also because “you can’t imagine any of Taylor Swift’s competitors coming up with anything remotely like it.”
Song highlight: “Rain came pouring down when I was drowning / That’s when I could finally breathe.”
If you like this, listen to: “Daylight.”
“Blank Space” expertly mocked the boy crazy perception of Swift, while helping her shed it forever.
Swift’s 2014 album “1989” has been hailed as a pop masterpiece, and it in part deserves that acclaim thanks to the satirical “Blank Space.”
The track, which was nominated for three Grammy Awards, is “a thrillingly vicious riff on Swift’s reputation as a man-eater,” according to Mikael Wood of The Los Angeles Times.
While Swift would later analyze the perception of her public persona more fully on 2017’s “Reputation,” it was “Blank Space” that first gave her the means to call out the media in a record-breaking, chart-topping way.
Song highlight: “‘Cause darling I’m a nightmare dressed like a daydream.”
If you like this, listen to: “Getaway Car.”
“Holy Ground” makes a strong case that not all breakup songs have to be slow and sad.
In Idolator’s review for 2012’s “Red,” Sam Lansky named “Holy Ground” the album’s “most startling song,” writing that the “storming drum beat brings a sense of urgency that Swift’s sprawling soft-rock productions have rarely had.”
Lansky added that the “lyrics are classic Swift, with a couplet that’s brilliantly tight and so obvious it seems like it should have been the hook in a thousand pop songs already: “Tonight I’m gonna dance for all that we’ve been through/But I don’t wanna dance if I’m not dancing with you.”
Song highlight: “We blocked the noise with the sound of ‘I need you’ / And for the first time I had something to lose.”
If you like this, listen to: “State of Grace.”
“Sparks Fly” became a fan favorite before it was even released.
“Sparks Fly” is so perfectly Swiftian that this song — which was written by a 16-year-old Swift before her eponymous debut — garnered more than enough interest to convince the singer to rework it and release it on her third studio album, “Speak Now.”
As Jonathan Keefe wrote for Country Universe, this track is “a testament to everything Taylor Swift gets right.”
Song highlight: The dramatic urgency of “Drop everything now / Meet me in the pouring rain / Kiss me on the sidewalk / Take away the pain.”
If you like this, listen to: “Fearless.”
“White Horse” won the Grammys for best country song and best female country vocal performance in 2010.
A Billboard review of “White Horse” called it a “beautiful, understated ballad that showcases her skill with a lyric and shines a spotlight on her signature tender, heart-on-her-sleeve vocals,” adding, “Heartbreak has rarely sounded as compelling.”
Song highlight: “This is a big world, that was a small town / There in my rear view mirror disappearing now.”
If you like this, listen to: “Breathe.”
“Love Story” has been widely considered as Swift’s signature song.
“Love Story,” is “perhaps the moment when Swift’s songwriting prowess first fully revealed itself,” Alexis Petridis wrote for The Guardian, adding that it’s a “fantastic song.” Petridis also ranked “Love Story” at No. 2 in a list of Swift’s best songs.
While Swift left country behind, she brought “Love Story” with her into the pop space, layering new production on top of it to make it fit flawlessly amongst her later works. As Hazel Cills wrote for Pitchfork, “Swift’s great remake of ‘Love Story’ in slick 1989-era production is proof of its timelessness.”
Song highlight: “Romeo, save me, they’re trying to tell me how to feel / This love is difficult, but it’s real.”
If you like this, listen to: “You Belong With Me.”
“ME!” felt like a major misstep in setting the tone for “Lover.”
Longtime fans know Swift’s lead singles tend to be red herrings, and “ME!” might be the best example of a leading track expertly masking the overall feel of the album it’s meant to promote. But on what has been described as Swift’s most indie-leaning record to date, “ME!” is a sugary, too-sweet outlier fit for the “Frozen” demographic — and not much else.
Worst offense: Dragging Brendon Urie into this mess.
Saving grace: At least “Hey kids! Spelling is fun!” was left off the album version.
“Sad, Beautiful, Tragic” felt like it was written just for the sake of having another sad song on “Red.”
At four minutes and 44 seconds, “Sad, Beautiful, Tragic,” is the fourth longest song on 2012’s “Red,” but unlike similarly lengthy songs like “All Too Well” and “State of Grace,” the timing never quite felt warranted.
The song drags on — not because Swift has a lot to say like she usually does — but because she felt the need to sing a variation of the title 11 times as slowly as she could.
Worst offense: Swift could have used this time on the album for an “All Too Well” reprise made from the lyrics she ultimately cut.
Saving grace: “And time is taking its sweet time erasing you / And you’ve got your demons, and, darling, they all look like me.”
“Back to December” sees Swift crawling back to an ex that you wish she’d just get over.
Another song that felt sad for the sake of being sad, 2010’s “Back to December” was Swift’s first attempt at writing a song-apology, and it didn’t do a whole lot for her. At its best, it’s a song about reflecting on the role she played in an ill-fated relationship — but at its worst, it’s downright whiny.
Worst offense: Knowing it’s rumored to be about the werewolf from “Twilight” — even nine years on.
Saving grace: “It turns out freedom ain’t nothing but missing you.”
“Look What You Made Me Do” made for a great music video, but a terrible listening experience on its own.
“Look What You Made Me Do” was the first song Swift released after Kimye-gate tore her down in the court of public opinion and it didn’t do all that much to convince people to like her again — mostly because it wasn’t up to par with Swift’s earlier (and vastly superior) songwriting.
Pitchfork‘s Meaghan Garvey summed the track up perfectly when she wrote: “In her past work, Swift has flexed a real talent for molding real-life experiences into clue-filled allegories, at once personal and universal. Here, she’s uncharacteristically un-nuanced, and when she slips in hilariously artless digs like ‘I don’t like your tilted stage,’ it sounds like the part of a break-up when you start hurling all the banal insults you’ve got left.”
Worst offense: Swift apparently forgot how to write a chorus while making this song.
Saving grace: The music video is so deliciously petty and self-involved that it actually works.
“This Is Why We Can’t Have Nice Things” is an example of why we can’t have nice things.
Before “Reputation” came out, many believed it would be littered with West-diss tracks just like this one, so it’s a shame that when the album proved to be a broader reflection of Swift’s image and the effect it had on her personal relationships, she didn’t leave “This Is Why We Can’t Have Nice Things” on the cutting room floor — or at least shove it onto the album earlier.
“This is Why We Can’t Have Nice Things” is a final jab at West that unnecessarily disrupted the emotional flow of “Dress,” “Call It What You Want,” and “New Year’s Day” on the back end of the record.
Worst offense: The placement on the album.
Saving grace: The image of Taylor’s mom, Andrea Swift, having to sit through endless rants about Kim Kardashian West and Kanye West.
“Bad Blood” was a lackluster attempt at dissing Katy Perry.
Rolling Stone’s Sheffield ranked “Bad Blood” dead last out of Swift’s 129 songs, calling it, “melodically parched, lyrically unfinished, [and] rhythmically clunky.”
Before “1989” dropped in October 2014, Swift prefaced the track by saying it was about a fellow singer who “did something so horrible” to her. And while that would be more than enough to excite fans about the song, the end result was “disappointingly bland,” Andrew Unterberger wrote for Spin.
Unterberger added: “There are precious few of Taylor’s trademark particulars to provide any kind of direction as to the subject, and in fact, the whole thing is couched with ‘baby’ and ‘mad love’ references that make the song sound more about a romantic relationship than a broken friendship.”
Worst offense: Igniting a full-blown feud with Katy Perry.
Saving grace: Kendrick Lamar (who’s featured on the song) doesn’t hate it?
“Better Than Revenge” didn’t age well, especially after Swift learned about feminism.
If there’s one underlying theme running throughout Swift’s worst songs, it’s that there is nothing she does worse than revenge.
Whether she’s calling out the Wests or fighting with Perry, the tracks Swift wields as weapons to win feuds often fall flat — but “Better Than Revenge” has even more working against it in the age of mainstream feminism and woke Twitter. In particular, the line, “She’s better known for the things that she does on the mattress,” with its slut-shaming overtones isn’t kosher anymore (if it ever was).
Worst offense: Reportedly slut-shaming Camilla Belle for having the audacity to date Joe Jonas.
Saving grace: Swift acknowledged her bad judgment on the lyrics when she told The Guardian in 2014, “I was 18 when I wrote that … That’s the age you are when you think someone can actually take your boyfriend. Then you grow up and realize no one can take someone from you if they don’t want to leave.”
“Santa Baby” was a strange pick to cover as a teenager.
Being the December baby that she is, it’s not much of a surprise that Swift came out with a Christmas EP in 2007 called “The Taylor Swift Holiday Collection.”
But considering she was still a teenager when she released her cover of “Santa Baby,” it’s difficult to listen to a young Swift croon about how she’s been an “awful good girl” while trying to flirt her way into a light blue convertible without gagging.
Worst offense: Covering this song in the first place.
Saving grace: It’s not Michael Bublé’s no-homo cover that refers to Kris Kringle as “Santa buddy.”
While critics thought “…Ready for It?” was better than its predecessor, “Look What You Made Me Do,” it was still labeled as “not good.”
After “…Ready for It?” hit airwaves in 2017, Mike Wass wrote of the track for Idolator, “If you can get past the cringeworthy lyrics and jarring production, a cute chorus awaits. But that’s a lot of work for a minor payoff.”
Spin’s Jordan Sargent also called the song “ill-fitting,” while Vulture’s Craig Jenkins said it “doesn’t reinvent pop or Taylor, but it does get her name out on a product built to keep pace with current trends.”
Jenkins added that he couldn’t understand “why her reinvention is centered in rap flows and flashy eight-counts, her two worst skill sets.”
Worst offense: “Younger than my exes but he act like such a man, so.”
Saving grace: “And he can be my jailer, Burton to this Taylor.”
It’s unclear why “How You Get the Girl” exists.
“How You Get the Girl” is a guide for a straight man on how to win back his ex-girlfriend six months after the breakup — but if the relationship ended, it probably ended for a reason. In the name of “girl code,” this message sucks for every female fan listening.
Now, if Swift wrote a song about how women should definitely not take their exes back, that’d be something worth listening to.
Worst offense: Encouraging men to pester their exes for another chance at a relationship.
Saving grace: It provides a built-in 4-minute bathroom break for those listening to “1989” in full.
“Welcome to New York” has been criticized for not being an accurate portrayal of life in NYC.
Swift loves the Big Apple, and while some of her songs that mention the city — “Cornelia Street,” “Holy Ground” — made it into the top 15 on this list, her outright ode to New York missed the mark completely with its exhausting optimism. Julianne Escobedo Shepherd of Jezebel went so far as to call it a “gentrification anthem.”
At the time of its release, actress and rapper Awkwafina told Gothamist that the track was “one of those songs that, with just one single radio play, will make at least 10 New Yorkers move to Marfa, Texas.”
Worst offense: Saying she “wouldn’t change anything, anything, anything,” about New York — likely because she hasn’t had to go anywhere near the subway since her 2009 MTV Video Music Awards performance.
Saving grace: “And you can want who you want / Boys and boys and girls and girls.” Also, when it was released ahead of “1989” as a promotional single, Swift donated all proceeds to the New York City Department of Education.
“London Boy” would “be cool if it were Estelle’s 2008 banger ‘American Boy'” — but it’s far from it.