Here is a very special collection of the top 30 most amazing and successful Taylor Swift songs.
Before Taylor Swift came along, country music was basically music made by adults, all of that changed with Swift. She was singing from a teenager’s perspective. There’s a stamp on the country music timeline that clearly acknowledges the Swiftian era – before and after – because once she arrived, everything changed.
SANTA MONICA, February 6, 2020 – Taylor Swift, one of the music industry’s most creatively and commercially successful artist-songwriters in history, signed an exclusive global publishing agreement with Universal Music Publishing Group (UMPG), a leading global music publisher. “I’m proud to extend my partnership with Lucian Grainge and the Universal Music family by signing with UMPG, and for the opportunity to work with Jody Gerson, the first woman to run a major music publishing company,” said Taylor Swift.
Let‘s see together the “30 Best Taylor Swift Songs” as Vulture and holler ranks.
30- “White Horse” Fearless (2008)
The guiding principle on much of Red seems to have been to throw absolutely every idea a person could think of into a song and see what worked. Here, we go from Kelly Clarkson verses to a roller-coaster chorus to a dubstep breakdown that dates the song as surely as radiocarbon — then back again. It shouldn’t hang together, but the gutsy vocals and vivid lyrics keep the track from going off the rails.
29- “Teardrops on My Guitar” Taylor Swift (2006)
An evocative 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.
28- “Delicate” Reputation (2017)
With multitracked, breathy vocals, this is Swift at her most tentative. Would any other album’s Taylor be asking, “Is it cool that I said all that?” On an album where Swift attempted to play the villain without much success, the vulnerability plays better: This is the most genuinely sexy song on Reputation and one of Best “Taylor Swift Songs”.
27- “Begin Again” Red (2012)
Swift’s sequencing genius strikes again: After the emotional roller coaster of Red, this gentle ballad plays like a cleansing shower. (It works so well she’d repeat the trick on 1989 and Reputation.) Of all Swift’s date songs, this one feels the most true to life; anyone who’s ever been on a good first date can recall the precise moment their nervousness melted into relief.
26- “Soon You’ll Get Better” (2019)
Nestled in amongst all the summery pop froth of Taylor’s seventh album, Lover, was this sparsely orchestrated country lullaby and one of the most personal songs Taylor has ever written.
Featuring The Chicks on backing vocals, she wrote it about the battles that both of her parents have had with cancer, after her mother, Andrea, had been diagnosed with a brain tumour.
“It’s something I’m so proud of. I can’t sing it. It’s hard to emotionally deal with that song”, she said about the song when it came out. This one of the best “Taylor Swift Songs”.
25- “Shake It Off” 1989
Swift’s second No. 1 was greeted with widespread critical sighs: After the heights of Red, why was she serving up cotton-candy fluff about dancing your way past the haters? (Never mind that Red had its own sugary singles.) Now that we’ve all gotten some distance, the purpose of “Shake It Off” is clear: This is a wedding song, empty-headed fun designed to get both Grandma and Lil Jayden on the dance floor. Docked ten or so spots for the spoken-word bridge and cheerleader breakdown, which might be the worst 24 seconds of the entire album.
The lyrics – written about a couple in an unhealthy relationship from which they couldn’t disentangle themselves – were full of clues to late-night drives, lipstick shades and long slicked-back hair.
Taylor finally put an end to fifteen years of Reddit posts when she confirmed the song was written about ex-boyfriend Harry Styles in an interview with Rolling Stone in 2014.
23- “Fearless” Fearless (2008)
he title track from Swift’s second album has more of her favorite images — in one memorable twofer, she’s dancing in the rain while wearing her best dress — but she invests them with so much emotion that you’d swear she was using them for the first time. The exuberance of the lyrics is matched in the way she tumbles from line to line into the chorus.
22- “Tim McGraw” Taylor Swift (2006)
f you by chance ever happen to meet Taylor Swift, there is one thing you should know: Do not, under any circumstances, call her “calculating.” “Am I shooting from the hip?” she once asked GQ when confronted with the word. “Would any of this have happened if I was? … You can be accidentally successful for three or four years.
Accidents happen. But careers take hard work.” However, since the title of her first single apparently came from label head Scott Borchetta — “I told Taylor, ‘They won’t immediately remember your name, they’ll say who’s this young girl with this song about Tim McGraw?’” — I think we’re allowed to break out the c-word: Calling it “Tim McGraw” was the first genius calculation in a career that would turn out to be full of them. Still, there would have been no getting anywhere with it if the song weren’t good. Even as a teenager, Swift was savvy enough to know that country fans love nothing more than listening to songs about listening to country music. And the very first line marks her as more of a skeptic than you might expect: “He said the way my blue eyes shined put those Georgia pines to shame that night / I said, ‘That’s a lie.’” This one of the best “Taylor Swift Songs”.
21- “Fifteen” (2009)
“In your life you’ll do things greater than dating the boy on the football team, but I didn’t know it at fifteen”, sings Taylor on the fourth single from Fearless.
A true-to-life tale of high school heartbreak, it was inspired by Swift’s first freshman year at Hendersonville High School, where she says she had her heartbroken for the first time, along with her best friend Abigail Anderson.
The song, which doubles up as a cautionary tale for teenage girls, was so personal to Taylor that she cried when she was recording it, admitting that it still gets to her all these years later when she performs it live.
20- “I Did Something Bad” Reputation (2017)
It’s too bad Rihanna already has an album called Unapologetic, because that would have been a perfect title for Reputation, or maybe just this jubilant “Blank Space” sequel. Why the hell she didn’t release this one instead of “Look What You Made Me Do,” I’ll never know — not only does “Something Bad” sell the lack of remorse much better, it bangs harder than any other song on pop radio this summer except “Bodak Yellow.” Is that a raga chant? Are those fucking gunshots? Docked a spot or two 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 “shit.” This one of the best “Taylor Swift Songs”.
19- “Dear John” Speak Now (2010)
“I’ve never named names,” Swift once told GQ. “The fact that I’ve never confirmed who those songs are about makes me feel like there is still one card I’m holding.” That may technically be true, but she came pretty dang close with this seven-minute epic. (John Mayer said he felt “humiliated” by the song, after which Swift told Glamour it was “presumptuous” of him to think that the song his ex wrote, that used his first name, was about him
She sings the hell out of it, but when it comes to songs where Swift systematically outlines all the ways in which an older male celebrity is an inadequate partner, I think I prefer “All Too Well,” which is less wallow-y. I’ve seen it speculated that the guitar noodling on this track is meant as a parody of Mayer’s own late-’00s output, which if true would be deliciously petty.
18- “Red” Red (2012)
Re-eh-eh-ed, re-eh-eh-ed. Red’s title track sees the album’s maximalist style in full effect — who in their right mind would put Auto-Tune and banjos on the same track? But somehow, the overstuffing works here; it’s the audio equivalent of the lyrics’ synesthesia.
17- “Cardigan” 2020
While we were all baking banana bread and doing Joe Wicks workouts, Taylor was busy spending the first COVID lockdown completely reinventing herself.
She spent it recording not one but TWO new albums (as well as rerecording a third), with The National’s Aaron Dessner at the helm.
Written with Dessner, ‘cardigan’ was the lead single from Folklore; a slow-burning indie ballad about young love and lost innocence.
It was told from the perspective of a female narrator called Betty, one of several fictional characters that the Swiftiverse was about to become very familiar with. This one of the best “Taylor Swift Songs”.
16- “Forever & Always” Fearless (2008)
This blistering breakup song was the one that solidified Swift’s image as the pop star you dump at your own peril. (The boys in the debut were just Nashville randos; this one was about a Jonas Brother, back when that really meant something.) Obligatory fiddles aside, the original version is just about a perfect piece of pop-rock — dig how the guitars drop out at a pivotal moment — though the extended edition of Fearless also contains a piano version if you feel like having your guts ripped out.
I have no idea what the lines about “rain in your bedroom” mean, but like the best lyrics, they make sense on an instinctual level. And to top it off, the track marks the introduction of Swift’s colloquial style — “Where is this GOoO-ING?” — that would serve her so well in the years to come. This one of the best “Taylor Swift Songs”.
15- “Mean” Speak Now (2010)
It takes some chutzpah to put a song complaining about mean people on the same album as “Better Than Revenge,” but lack of chutzpah has never been Swift’s problem. Get past that and you’ll find one of Swift’s most naturally appealing melodies and the joyful catharsis that comes with giving a bully what’s coming to them. (Some listeners have interpreted the “big enough so you can’t hit me” line to mean the song’s about abuse, but I’ve always read it as a figure of speech, as in “hit piece.”)
14- “Begin Again” 2012
The closing song on Red found Taylor returning momentarily to her country roots for one last look around; all before she went off into the world of pop forever.
As Taylor describes it, it’s a song “about when you’ve gotten through a really bad relationship, you finally dust yourself off and go on that first date after – and all the vulnerability that goes along with that”.
In the video, Taylor is seen riding a bicycle along the cobbled streets of Paris; shopping for clothes, sipping cappuccinos in Parisian cafés and generally living her best life.
13- “Hey Stephen” Fearless (2008)
Who knew so many words rhymed with Stephen? They all come so naturally here. Swift is in the zone as a writer, performer, and producer on this winning deep cut, which gives us some wonderful sideways rhymes (“look like an angel” goes with “kiss you in the rain, so”), a trusty Hammond organ in the background, and a bunch of endearing little ad-libs, to say nothing of the kicker: “All those other girls, well they’re beautiful / But would they write a song for you?” For once, the mid-song laugh is entirely appropriate. One of the best 30 “Taylor Swift Songs”.
12- “Out of the Woods” 1989 (2014)
Like Max Martin, Antonoff’s influence as a collaborator has not been wholly positive: His penchant for big anthemic sounds can drown out the subtlety of Swift, and he’s been at the controls for some of her biggest misfires. But boy, does his Jack Antonoff thing work here, bringing a whole forest of drums to support Swift’s rapid-fire string of memories. The song’s bridge was apparently inspired by a snowmobile accident Swift was in with Harry Styles, an incident that never made the tabloids despite what seemed like round-the-clock coverage of the couple — a subtler reminder of the limits of media narratives than anything on Reputation.
11- “Wildest Dreams,” 1989 (2014)
One of the best 30 “Taylor Swift Songs”. Swift is in full control of her instrument here, with so much yearning in her voice that you’d swear every breath was about to be her last. For a singer often slammed as being sexless, those sighs in the chorus tell us everything we need to know. Bumped up a few spots for the invigorating double-time bridge, the best on 1989.
10- “New Year’s Day”
It’s the day after the high drama house party that was Reputation, as the album closes out and Taylor is left to clean up the absolute mess from the night before.
Written after a party at her London home, the delicate piano ballad gave us a moment’s pause to reflect at the end of the album, signposting less stormy waters ahead.
“I was thinking about how everybody talks and thinks about who you kiss at midnight”, Taylor explained about the song’s origins. “But I think there’s something even more romantic about who’s gonna deal with you on New Year’s Day. Who’s willing to give you Advil and clean up the house? I think that states more of a permanence”.
Olivia Rodrigo would go on to interpolate the piano chords for her song ‘1 Step Forward, 3 Steps Back’. One of the best 30 “Taylor Swift Songs”.
9- “State of Grace” Red (2012)
One of the best 30 “Taylor Swift Songs”. Swift’s songs are always full of interesting little nuggets you don’t notice until your 11th listen or so — a lyrical twist, maybe, or an unconventional drum fill — but most of them are fundamentally meant to be heard on the radio, which demands a certain type of songwriting and a certain type of sound. What a surprise it was, then, that Red opened with this big, expansive rock track, which sent dozens of Joshua Tree fans searching for their nearest pair of headphones. Another surprise: that she never tried to sound like this again. Having proven she could nail it on her first try, Swift set out to find other giants to slay.
8- “Love Story,” Fearless (2008)
Full disclosure: This was the first Taylor Swift song I ever heard. (It was a freezing day in early 2009; I was buying shoes; basically, the situation was the total antithesis of anything that’s ever happened in a Taylor Swift song.) I didn’t like it at first. Who’s this girl singing about Romeo and Juliet, and doesn’t she know they die in the end? What I would soon learn was: not here they don’t, as Swift employs a key change so powerful it literally rewrites Shakespeare. The jury’s still out on the question of if she’s ever read the play, but she definitely hasn’t read The Scarlet Letter. One of the best 30 “Taylor Swift Songs”.
7- “I Knew You Were Trouble”
Even before 1989, Taylor was getting inspiration from her failed romance with Harry Styles.
After a feisty performance of this song at the Brits in 2013 – where Styles was in the audience – she admitted that it wasn’t “hard to access that emotion when the person the song is directed at is standing side of the stage watching”.
Written with Max Martin and Shellback, ‘I Knew You Were Trouble’ was Taylor mixing the stadium-sized country-pop of Shania with the all-out pop of Britney to devastating effect, even managing to mix a little dubstep into the song’s refrain.
6- “Our Song” Taylor Swift (2006)
Other amazing piece of the best 30 “Taylor Swift Songs”. Swift wrote this one for her ninth-grade talent show, and I have a lovely time imagining all the other competitors getting the disappointment of their lives once they realized what they were up against. (“But nice job with that Green Day cover, Andy.”) Even at this early stage Swift had a knack for matching her biggest melodic hooks to sentences that would make them soar; that “’cause it’s late and your mama don’t know” is absolutely ecstatic. She’s said she heard the entire production in her head while writing, and on the record Nathan Chapman brings out all the tricks in the Nashville handbook, and even some that aren’t, like the compressed hip-hop drums in the final refrain.
5- “Mine” Speak Now (2010)
As catchy as her Max Martin songs, but with more of a soul, “Mine” wins a narrow victory over “Our Song” on account of having a better bridge. This one’s another fantasy, and you can kind of tell, but who cares — Paul McCartney didn’t really fall in love with a meter maid, either. Swift packs in so many captivating turns of phrase here, and she does it so naturally: It’s hard to believe no one else got to “you are the best thing that’s ever been mine” before her, and the line about “a careless man’s careful daughter” is so perfect that you instantly know everything about the guy. Let’s give a special shout-out to Nathan Chapman again: His backup vocals are the secret weapon of Speak Now, and they’re at their very best here. One of the best 30 “Taylor Swift Songs”.
4- “Blank Space” 1989 (2014)
You know how almost every other song that’s even a little bit like “Blank Space” ranks very low on this list? Yeah, that’s how hard a trick Swift pulls off on this 1989 single, which manages to satirize her man-eater image while also demonstrating exactly what makes that image so appealing. The gag takes a perfectly tuned barometer for tone: “Look What You Made Me Do” collapsed under the weight of its own self-obsession; “Better Than Revenge” didn’t quite get the right amount of humor in. But Swift’s long history of code-switching works wonders for her here, as she gives each line just the right spin — enough irony for us to get the jokes, enough sincerity that we’ll all sing along anyway. Martin and Shellback bring their usual bells and whistles, but they leave enough empty space in the mix for the words to ring out. Who wouldn’t want to write their name?. One of the best 30 “Taylor Swift Songs”.
3- “The Man” 2019
This incendiary take-down of society’s sexist double standards from the Lover album saw Taylor turning a corner into a more politically conscious stage of her career.
Upturning the tables on the media’s perception of her, she wondered how different those perceptions would be if she was male.
The video, directed by Taylor herself, sees her acting the role of her male alter-ego “Tyler Swift”.
2- “All Too Well” Red (2012)
t’s no wonder that music writers love this one: This is Swift at her most literary, with a string of impeccably observed details that could have come out of a New Yorker short story. “All Too Well” was the first song Swift wrote for Red; she hadn’t worked with Liz Rose since Fearless, but she called up her old collaborator to help her make sense of her jumble of memories from a relationship recently exploded. “She had a story and she wanted to say something specific. She had a lot of information,” Rose told Rolling Stone later.
1. “You Belong With Me” Fearless (2008)
Swift was hanging out with a male friend one day when he took a call from his girlfriend. “He was completely on the defensive saying, ‘No, baby … I had to get off the phone really quickly … I tried to call you right back … Of course I love you. More than anything! Baby, I’m so sorry,’” she recalled. “She was just yelling at him! I felt so bad for him at that moment.” Out of that feeling, a classic was born. Swift had written great songs drawn from life before, but here she gave us a story of high school at its most archetypal: A sensitive underdog facing off with some prissy hot chick, in a battle to see which one of them reallygot a cute boy’s jokes. (Swift would play both women in the video; she had enough self-awareness to know that most outcasts are not tall, willowy blonde girls.) Rose says the song “just flowed out of” Swift, and you can feel that rush of inspiration in the way the lines bleed into each other, but there’s some subtle songcraft at work, too: Besides the lyrical switcheroos about who wears what, we also only get half the chorus the first go-round, just to save one more wallop for later. The line about short skirts and T-shirts will likely be mentioned in Swift’s obituary one day, and I think it’s key to the song’s, and by extension Swift’s, appeal: In my high school, even the most popular kids wore T-shirts.