The 25 Best Taylor Swift Songs, Ranked
Taylor Swift released her first album in 2006, when she was just 16 years old. Now at 33, the singer-songwriter has become the voice of love, heartbreak, and every emotion in between. The singer just released her 10th album — not counting the three rerecordings she's released so far, including July's "Speak Now (Taylor's Version)" — and she's shown no sign of slowing down. Swift is currently in the middle of her Eras Tour, where she's picked 44 songs from her catalog to perform for fans across the US. Swift has released more than 230 songs in total, and at POPSUGAR, we decided to rank just the 25 very best Swift songs.
My methodology was both highly scientific and highly personal. I went through Swift's discography and put songs that I thought might make the cut into a playlist. That playlist ended up having 43 songs (and it included no Christmas tracks, though I am an avowed "Christmas Tree Farm" fan). I made a new playlist and began the painful process of cutting 18 songs to get the final 25. I tried not to consider which songs are my personal favorite; quite a few of the ones that I put on replay didn't even make the 43-song cut. But I considered which are Swift's most important, her most lyrically or musically impressive, or her most iconic.
Ahead, these are POPSUGAR's top 25 Taylor Swift songs.
"Out of the Woods" by Taylor Swift
Swift has a reputation for demolishing her past relationships — and past partners — in songs, but "Out of the Woods" from 2014's "1989" is a great example of looking back with regret, but not vitriol. "Out of the Woods" is about how a relationship can't thrive under the spotlight and the suffering that happens when you feel like you're always on the run. When the chorus comes in one final time at the end, you can't help but scream along.
"Forever & Always (Piano Version) (Taylor's Version)" by Taylor Swift
The original version of "Forever & Always" sets Swift's heartbreaking lyrics over a faster beat; the piano version really gives the suffering the spotlight, and I was thrilled Swift included a new rendition of the piano version on "Fearless (Taylor's Version)" in 2021. Swift has solo writing credits on the track, and she beautifully captures the ubiquity of heartbreak: "It rains when you're here and it rains when you're gone." So much of 2008's "Fearless" and 2010's "Speak Now" plays with the ideas of stories and fairy tales, and "Forever & Always" is about when "once upon a time" goes wrong.
"New Year's Day" by Taylor Swift
"Reputation," released in 2017, gave us some of Swift's best love songs. One of the things that sets "New Year's Day" apart is how fragile it all feels. Swift sings that she's just had a lovely New Year's Eve — glitter on the floor, shoes in the lobby. And yet, while she's enjoying the afterglow of this night and the dawn of a New Year, she can't help but try to hold on to her lover a little too tight. "Please don't ever become a stranger whose laugh I could recognize anywhere," she asks, haunted by past losses and afraid of a future that could hold even more. It's bittersweet romance at its best. Plus, society has always needed more songs about New Year's. Swift provides.
"Enchanted (Taylor's Version)" by Taylor Swift
"Enchanted," from 2010's "Speak Now" (and the 2023 "Taylor's Version"), is a theme song for hopeless romantics. Swift perfectly describes the night you first meet someone and immediately can picture your lives coming together. But even in this sweeping, over-the-top tale of running away with a romantic fantasy, Swift can't help but worry. "Please don't be in love with someone else," she begs of her new crush. We've all been there.
"Wildest Dreams," a track on "1989," just missed the cut for this list, but the "Enchanted/Wildest Dreams" mashup from the "1989" tour in 2015 remains one of her best live performances of all time, and if she put it on an album, it would easily be top five on this very list.
"Ivy" by Taylor Swift
Swift's fans often complain that the artist has not shown enough love to "Evermore," the second album she released in 2020, but she has used her Eras tour to give many of the tracks their moment in the sun. "Ivy" isn't on the set list, which is a mistake. The song, about a married woman who falls for someone who's not her husband, evokes for me "Portrait of a Lady on Fire" or "Madame Bovary" — something majestic and sweeping and deeply intense. The lyrics breathe new life into cottagecore cliches of ivy and clover, filling them with pain and suffering but also love and lust.
"Dancing With Our Hands Tied" by Taylor Swift
Swift has quite a few songs about the difficulties of falling in love — and having a sex life — as a public figure, but "Reputation"'s "Dancing With Our Hands Tied" is the most sensual of those songs. Whether you think it's about Swift's ex-boyfriend Joe Alwyn or another relationship fans aren't privy too, it's about getting to be together and explore each other in private, while keeping away from each other in public. The image of "dancing with our hands tied" is both sad — they can't touch — and a little sexy, too.
"Nothing New (Taylor's Version) (From the Vault)" by Taylor Swift Feat. Phoebe Bridgers
I'm a big fan of the "From the Vault" songs on Swift's rerecordings — tracks she wrote for those albums that didn't make it to the final cut that she's resurrected for the new releases. Many are excellent, but "Nothing New (Taylor's Version)" from 2021's "Red (Taylor's Version)" clearly rises above the rest. Swift pairs up with Phoebe Bridgers for this duet about the fear of growing older and the uncertainty that comes with the passage of time. "How long will it be cute, all this crying in my room?" Bridgers sings. Is an adult woman allowed to have emotions, a rich interior life, that includes being sad? Can society move past its obsession with youth? There are no answers here, just lots of questions.
"Holy Ground (Taylor's Version)" by Taylor Swift
Swift doesn't get enough credit for being funny in her lyrics, and "Holy Ground," from "Red," is a prime example of that. Swift has been criticized for rushing into relationships, and she satirizes that in the start of this song. She lists all these things her and her lover did together then says: "And that was the first day." All that in a day? It's romance on speed dial, and that can be really, really fun, the way it is in "Holy Ground."
"Style" by Taylor Swift
"Style," a "1989" track, is a great pop song. It gets stuck in your head and it stays there. Based on the name, it seems to be about Swift's ex Harry Styles, and it's a fitting tribute to the brief relationship between two pop icons. "Style" and "1989" as a whole are also a good demarcation point for a sexier, more sensual era of Swift's discography. She may have been famous since she was 16, but she's not a little girl anymore.
"Seven" by Taylor Swift
The next three songs — "Seven," "August," and "Mirrorball" — also appear in a row on Swift's 2020 album "Folklore," and it is the best three-song run in all of Swift's discography. "Seven" is an emotional look back at childhood and the things that don't make sense when you're young that make sick, upsetting sense now. In the bridge she sings, "And I've been meaning to tell you / I think your house is haunted / Your dad is always mad and that must be why," a glimpse of childlike logic that's so heavy to hold. It's the heartbreak of realizing adults mistreated you and your friends and that you didn't deserve it at all.
"August" by Taylor Swift
"August" is part of a trio of songs on "Folklore" Swift has said show three sides of the same love triangle, along with "Cardigan" and "Betty." But "August" is from the girl who doesn't get the happy ending in the love triangle, who has one golden summer and sees it all slip away. It's painful and brilliant. There are many songs about the magic of summer love, but "August" is about the doldrums of summer, the anguish of the eighth month of the year.
"Mirrorball" by Taylor Swift
Who knew a mirrorball could be so depressing? In "Mirrorball," Swift compares herself to the sparkling globe, the center of the party but never actually a part of it. Swift sings of spinning around to amuse others, of her fragility, of her fears about her identity. As is often the case with Swift's songs, she really hits her stride in the bridge, singing, "I've never been a natural / All I do is try, try, try." Her anxieties are laid bare, and she owns them.
"Cowboy Like Me" by Taylor Swift
"Cowboy Like Me," off of "Evermore," is nominally about two con artists scamming rich people and trying not to fall in love with each other. But when Swift sings, "Forever is the sweetest con," it becomes clear that it's really about her fears about love. She's so confident on 2019's "Lover," and so unsure here. The real con is being in a relationship at all, and love here is heady, sharp, hard, and terrifying.
"Bigger Than the Whole Sky" by Taylor Swift
"Bigger Than the Whole Sky," one of the tracks added to the "3am" edition of 2022's "Midnights," is devastating as it describes the devastation of loss. Swift never says quite what this loss is — though many who've struggled with pregnancy loss have identified with its lyrics — but her sadness is overwhelming and beautifully rendered. Swift has a talent for turning her own pain into everyone's pain, of making space for everyone to just be sad without shame, and she never does it as beautifully as she does here.
"Fifteen (Taylor's Version)" by Taylor Swift
I was a teenager when "Fearless" came out in 2008, so of course "Fifteen" was one of the first Swift songs I loved. How could it not be? Pop music is for teenagers, but on both her debut album and "Fearless," Swift spoke right to the actual experiences that teenagers go through, and "Fifteen" was a message right to us. Swift chronicles the highs and lows of a year of high school and points to the future, where teenage drama won't matter as much — but that doesn't mean it doesn't matter at all. It's one of the earliest examples of her superb storytelling skills.
"Last Kiss (Taylor's Version)" by Taylor Swift
"All Too Well" might be the more famous lengthy Swift breakup song, but the utter devastation of "Last Kiss" can't be overlooked. "Last Kiss," off of "Speak Now," explores the sadness after a breakup for six unrelenting minutes. Again, the bridge is full of some of her best lines: "So I'll watch your life in pictures like I used to watch you sleep." Earlier this year, that line inspired its own TikTok trend, users mapping their own losses onto Swift's, another example of how she's able to make her pain bigger than her own experience of it. Swift moved on, but the tribute to her heartbreak is there forever.
"Clean" by Taylor Swift
Sometimes when I think about seeing Swift sing "Clean" in person on the "1989" tour, I can't help but get a little emotional. "Clean" is catharsis. A cleansing rainstorm is perhaps not the most unique metaphor in the world, but on this "1989" track, Swift gives the comparison new life, serving a perfect album-ender. Sara Bareilles and Kelly Clarkson have both covered the track, and Swift did a stripped-down piano version on her "Reputation" tour, and that's because its message of renewal after loss is so beautifully rendered in Swift's lyricism. What really makes her lyrics sing is the tiny little bit of fear that sneaks in. "I think I am finally clean," she sings — always leaving the possibility open that she isn't yet.
"Lavender Haze" by Taylor Swift
It's hard to rank songs from Swift's newest album, because you have to worry about recency bias. Is this song just novel, so I'm ranking it higher than it deserves? But "Lavender Haze" deserves its place. It is supremely catchy and fun, with smart, sharp lyrics. It takes on even more emotional resonances in light of her break up with Alwyn (Swift previously said he inspired the track, though she recently deleted that video from her Instagram account). "Lavender Haze" is tinged with the fear that they can't stay in the comfort of their relationship, that something will tear them apart. The fact that Swift was right tinges the track with tragedy that makes its joys just a little bit sweeter.
"Would've, Could've, Should've" by Taylor Swift
Based on the lyrics, fans have theorized that "Would've, Could've, Should've" is a revisit of the same ground Swift covered in "Dear John" way back on "Speak Now." Both, then, would be about her short fling with John Mayer when she was 19. "Dear John" is long and sad and heart-breaking. "Would've, Could've, Should've" is just as heartwrenching — but it's also absolutely furious. It's about how some things are so bad they stay with you for years, even if you want to be over them already. Swift looks back at the way she was treated and is even more angry than she was at the time. It's one thing to feel you were mistreated at 19; it's another to be 32 and known deep in your bones you absolutely were. "Would've, Could've, Should've" is cathartic fury at its finest.
"Cruel Summer" by Taylor Swift
"Cruel Summer" is a beloved song for many Swifties, partially because of the shine it never got. Swift did not make it a single off of 2019's "Lover," baffling some fans since it has "Song of the Summer" written all over it. Some theorized that the track was meant to be released as a single in 2020, but that the plan was derailed by the pandemic.
Whatever the case, Swift's "Cruel Summer" is one of her best. She cowrote the song with rocker St. Vincent and Swift's frequent collaborate Jack Antonoff, and the final product is propulsive, extremely catchy, and just plain fun. At the same time, the lyrics hint to some darkness underneath the summer fling: the uncertainty of a casual relationship weighs on her until she screams, "I love you, ain't that the worst thing you've ever heard?" The song's bridge is so powerful she sings it again as an outro, and we're always singing along.
"Love Story (Taylor's Version)" by Taylor Swift
"Love Story," from "Fearless," is the song that turned Taylor Swift, singer-songwriter, into Taylor Swift, pop star. It's the Swift song it seems like everyone knows. I remember at the time some lazy jokes about how Swift must have failed her high school English class; doesn't she know Romeo and Juliet die at the end?
But that's what makes this song so great and makes it emblematic not just of Swift's discography but of her entire outlook on love. "Love Story" is a tribute to romantic optimism, and Swift is queen of the romantic optimists. Reimagining a classic love story to have a happy ending is exactly what she should do. "It's a love story," she sings in every chorus, and if her discography had a headline, that would be it.
"Delicate" by Taylor Swift
In writing this ranking, I've realized how many of Swift's songs are steeped with anxiety, and "Delicate" is a song of early love for the anxious. It's when you tell someone you like them — a lot — and then immediately aren't sure if it was too much. The chorus — "Is it cool that I said all that? Is it too soon to do this yet?" — is so vulnerable, but still hopeful. She wouldn't have said it if she wasn't pretty sure the other person is feeling the same, but there's still the kernel of doubt.
"Blank Space" by Taylor Swift
"Blank Space" is when Swift strikes back — not at any one person, but at everyone. Everyone who joked she'd dated too many people and everyone who said she was obsessed with getting her heart broken so she could write more songs are in her line of fire. In "Blank Space," she owns the label that's been thrust upon her and takes it to its absurd, over-the-top ending. In addition to the genius lyrics, "Blank Space" is catchy as hell, a perfect song to blast in your car on a long stretch of highway.
"Daylight" by Taylor Swift
"Lover" is a criminally underrated Swift album, and "Daylight" is, in my opinion, her most underrated song. But not today. "Daylight" is about growth. Swift looks back at the the things she thought were love — the "burning red" highs of the "Red" era, the "black and white" anger of "Reputation" — and realizes both of those were just substitutions for the real thing. "It's golden," she sings in the bridge — "like daylight."
It's the most romantic song in Swift's discography and the perfect album-ender for "Lover."
"All Too Well (10 Minute Version) (Taylor's Version) (From the Vault)" by Taylor Swift
Surely many readers scrolled here first to see which track came in at No. 1, and they're probably not shocked to see "All Too Well (10 Minute Version)" here at the top. "All Too Well" — the original five-minute version from 2012's "Red" — was already one of Swift's best. In the shortened version, Swift pulled away the specifics of her doomed relationship to make a song of heartbreak and pain that felt universally relatable. In the 10-minute version (which she wrote first, though we had to wait years to hear it), she puts those specifics back in, reveals more about herself, and turns the song into undoubtedly her greatest masterpiece.
The 10-minute version is infused with the passage of time. "I remember it all too well," Swift sings on the choruses, and it becomes clear that the song is about reclaiming the memories, recounting the truth of her experiences. But the end is what always kills me, when she turns her focus solely on her ex. "Just between us, did the love affair maim you too?" she asks. There's no answer, of course; there never is. But she still gets to say what happened to her and reclaim her pain and heartbreak and anguish and turn it into something greater than a failed relationship and the person who left her bruised.