We’re counting down the 20 best songs ever from the global superstar, Taylor Swift.
20. “Our Song” from Taylor Swift
Where it all began. Though this twangy bop was technically the third single off of Taylor’s debut album (behind “Tim McGraw” and “Teardrops On My Guitar”), it’s proven to be the most signature of her first era. When you think of a blue-eyed, crimped-hair, sundress-clad Taylor Swift strumming her guitar, this is probably the song you hear in your head. It’s catchy, it’s romantic and it demonstrated early on Taylor’s knack for writing lyrics that paint a relatable picture of love. The fact that she wrote it for her ninth grade talent show? Now that’s herstory.
19. “You’re On Your Own, Kid” from Midnights
This has already proven to be one of the most enduring tracks off of Taylor’s latest album in many ways, and for good reason. The lyrics are particularly vulnerable and reflective of her journey through life so far, but it’s the bridge that really cemented this song’s place towards the top of the Swiftian canon. The line about friendship bracelets is what inspired Swifties of all ages to make and trade homemade jewelry at every stop along the Eras Tour, so it has certainly had an outsize impact. There’s a reason why this was one of the two songs included in the acoustic set in the tour’s accompanying concert film, baby!
18. “Anti-Hero” from Midnights
The song that had thousands of gays and basic bitches alike making “It’s me, hi! I’m the problem, it’s me” their Instagram captions. “Anti-Hero” falls in the lineage of some of T.Swift’s most self-aware bops, letting us into the self-loathing that she’s developed as her fame continues to skyrocket. It’s Taylor doing what she does best: Taking a specific feeling or experience from her extremely unrelatable life and making it, well, relatable. This song was No. 1 for eight weeks, and we love that for her.
17. “Getaway Car” from Reputation
One of the biggest Taylor Swift bops that she never made a single, “Getaway Car” is and always will be a standout from her Reputation era, which has aged like fine wine. If you didn’t get it back then, you get it now. (And if you don’t, lord help you.) This is Taylor and Jack Antonoff at their best together, giving us synths and an explosive, cinematic chorus and distorted vocals and Bonnie and Clyde references. Sometimes I dream about this getting the years-later single treatment a la “Cruel Summer” so it can finally get the moment in the spotlight it deserves.
16. “Back to December (Taylor’s Version)” from Speak Now (Taylor’s Version)
This giant ballad was the first big apology song that Taylor ever released, and it remains a doozy all these years later. The wistful lyrics capture that regretful feeling we all know of looking back fondly at a relationship that perhaps didn’t end in the best way, and her matured voice on the updated Taylor’s Version takes it to the next level. The lore of this song is also important, as it was released as the speculation around ~who her songs are about~ was reaching fever pitch. Taylor Lautner confirmed that he was the inspiration for this one, which makes it one of the most memorable things about him. Well, that and his abs.
15. “Cornelia Street” from Lover
At once romantic and heartbreaking and nostalgic, “Cornelia Street” is an obvious and lasting highlight from Lover that I think of as “All Too Well’s” little sister who moved to New York and got wrapped up in a city-spanning romance. The lyrics reference the massive townhouse that Taylor rented when her even more massive TriBeCa penthouse was under construction, which has made both the house itself and the one-block West Village street legit tourist destinations. No, really, if you walk down that street at any given time, there’s like a 90-percent chance you’ll see tweens filming TikToks of themselves in front of the house or street sign. In spite of that, “Cornelia Street” is a timeless ballad that will always rank as one of Taylor’s best.
14. “Don’t Blame Me” from Reputation
“Don’t Blame Me” went from being a somewhat cult favorite to a bop with more mainstream appeal after it went viral on TikTok in 2022. While it was never a single, its pulsating beat and gospel-backed vocals go undeniably hard. That high note that Taylor hits going into that rapturous final chorus? I get the fucking chills every time I hear it. You can also tell it’s a song that Taylor loves to sing, as it got a prominent slot on the Eras Tour. While one would never seriously label Taylor “edgy,” this self-aware, moody bop is as close as she gets to that — and it was co-written and produced by the pop dream team of Max Martin and Shellback, so it’s no wonder that it found its audience.
13. “Wildest Dreams (Taylor’s Version)” from 1989 (Taylor’s Version)
It turns out that Taylor doing Lana del Rey cosplay works incredibly well. Another collab with Max Martin and Shellbeck, “Wildest Dreams” takes a page from her pal Lana’s playbook and delivers a sexy plea to a former lover that builds over a heartbeat-like, pulsing beat. It’s sexier than Taylor had ever been up until this 1989 era, which really ripped her career and the possibilities for her music wide open. This is a Power Ballad that has stood the test of time over the past decade, proving to be one of her songs that appeals even to the biggest Taylor skeptics among us.
12. “We Are Never Ever Getting Back Together” from Red
Plucky and fun and sassy and inescapable, this taunting anthem to a desperate ex-boyfriend was Taylor’s first collaboration with Max Martin and Shellback, and it showed that they’re a match made in heaven: The song was her first of many No. 1 hits. (They didn’t return for the Taylor’s Version of Red, which resulted in this rerecording leaving a lot to be desired…) What really makes this one stick is that it’s unapologetic in its absolute pop-ness. Taylor wanted the world to know that she could be as pop as it gets, and I’m so glad she did. It might not be her deepest song lyrically, but it’s not trying to be that, either. When this song comes on, all she wants you to do is get up off your ass and dance, showing your ex that you’re totally over him and that you’re never ever getting back together — like, ever.
11. “Style” from 1989
On an album full of massive pop bops, “Style” has always managed to stand out from the pack. It simultaneously feels distinctly ‘80s with its synth-y guitar riff and also distinctly modern. In other words, it’s timeless. The straightforward lyrics about red lips and white t-shirts paint a vivid picture of a doomed, sexy, irresistible romance that, when you learn is all about her tryst with Harry Styles, becomes even hotter. The Taylor’s Version of “Style” is one of the most overt misfires of her rerecordings, as they couldn’t even come close to matching the production magic that Max Martin and Shellback brought to the original. This is a defining hit of one of Taylor’s most defining eras, cementing it as one of her best songs ever.
10. “Fifteen (Taylor’s Version)” from Fearless (Taylor’s Version)
There’s no better song that captures what it feels like to be a teenager than “Fifteen,” which Taylor wrote all on her own when she was still a teenager herself. While it’s technically about her redhead best friend named Abigail, it’s also about her and it’s also about you and me, when all you wanted was to be wanted. While the feelings you have when you’re a freshman in high school are often deemed quaint or trite or insignificant in hindsight, Taylor instead validates all of those complex emotions here. Whether it’s being on your very first date or dancing around your room when the night ends or your first kiss making your head spin ‘round, there’s so much to relate to here. It’s one of the earliest, most poignant instances of Taylor being so adept at putting feelings you didn’t even know you had into words. While her vocals on the original recording reflect her still-maturing perspective, the Taylor’s Version of “Fifteen” hits even harder because she’s reflecting on the experience of being a freshman in high school from the vantage point of her thirties. When she sings “wish you could go back and tell yourself what you know now,” she’s speaking to herself at 15 as a full-grown woman in her thirties who knows a thing or two.
9. “Long Live (Taylor’s Version)” from Speak Now (Taylor’s Version)
It’s the lyrics of “Long Live” that encapsulate what Taylor really did best over the course of her first three albums, using fairytale and small town high school imagery to produce a nostalgia-inducing ode to those closest to you. While she meant it as a dedication to her fans and the people in her band, it works just as well as any high school senior’s graduation song. Even if you’ve been out of school for a decade, listening to “Long Live” will have you longing for the days when you were part of the band of thieves in ripped up jeans ruling the world, fighting dragons with your high school girlies.
8. “Delicate” from Reputation
“Delicate,” another T.Swift x Max Martin and Shellback production, has proven to be the most lasting song from Taylor’s Reputation era — and for good reason. It’s Taylor’s best midtempo bop, and it came at a welcome time when she was going hard for a lot of the rest of that era. While the lyrics show her contending with the weight of her public image amid an electrifying new romance, she’s still somehow able to perfectly capture the butterflies of a budding relationship where you’re excited about a new guy but don’t want to get ahead of yourself and do something to scare them away.
7. “Love Story” from Fearless
In many ways, “Love Story” is the quintessential Taylor Swift song. It’s the blueprint. Forbidden romance, fairytale imagery, an unforgettable bridge, a booming final chorus that flips a narrative on its head — this tune has it all. While it’s the Taylor song that most obviously appeals to the straights (it’s kinda her “Toxic” if you think about it), to me that reflects its undeniable universal appeal. You may think you’re over this one, but then you hear it at a wedding and you hear that key change as Taylor chants “marry me, Juliet!” and you realize it’s impossible to ever be over a song this iconic.
6. “August” from Folklore
Salt air… and the rust on your door… in about four seconds, Taylor Swift takes you to the beach, to warmth, to a lazy summer day with your man of the moment. It’s a wistful, blissful, wishful song that is a standout from her folky soft-rock Folklore/Evermore pandemic era. While a lot of the material on those two albums represented an unexpected turn for her, “August” was for the non sad girls who still wanted some signature Swiftian qualities. It’s happy and sad at the same time, and it just works. You’ll never go another August without seeing at least 12 people captioning their monthly photo dumps with “August slipped away like a bottle of wine” which is basic, but also speaks to how much it connects with people.
5. “Enchanted (Taylor’s Version)” from Speak Now (Taylor’s Version)
This is one of Taylor’s best ballads ever, and I don’t say that lightly. There’s no better example of her songwriting prowess, no bigger build over the course of one of her songs and arguably no song more romantic than this. The way that the gentle acoustic guitar strums turn into an electric guitar and drum-infused chorus that booms from the rafters? Bliss. It makes you want to be in a football stadium full of fellow Swifties scream-singing this song at the top of your lungs while standing next to the love of your life. The repetition of “please don’t be in love with someone else, please don’t have somebody waiting on you” during the bridget? Chills! This is the song of her entirely self-written Speak Now era and is a fantastic bridge from the more youthful material of her first few albums and the more grown up feelings captured by the songs to follow.
4. “Cruel Summer” from Lover
The way that this song went from the ultimate “should’ve been a single” album track to being the earth-shaking opener of a record-breaking world tour that improbably reached No. 1 four years after its release? Now that’s what we call iconic. It’s all about that secrecy that can make a fleeting summer romance simultaneously so thrilling and so gutting. You want it to last, but you know it won’t. It’s booming and earworm-y and euphoric, and that’s before you get to the bridge, which is one of her best ever. It’s impossible to pick a favorite line from this treasure trove of one-liners: “I don’t want to keep secrets just to keep you,” “I love you, ain’t that the worst thing you ever heard?,” “Devils roll the dice, angels roll their eyes”… I could go on. “Cruel Summer” is, has been and always will be that girl, and you get the sense that this song is still building its legacy.
3. “Blank Space” from 1989
After years of headlines and narratives written about her, Taylor Swift entered her bad bitch pop era and proved once and for all that she’s way more self-aware than she’d ever gotten credit for. “Blank Space” playfully takes the media-painted image of her being a ruthless vixen who runs through men and uses relationships solely as fodder for her music and amplifies it to the extreme. It’s satire, and it’s catchy as all hell. The song, in addition to the music video — still the best of her career — demonstrated that she could be in on the joke, and it garnered her a lot of respect even from her harshest of critics. “Blank Space” is an undeniable bop of epic proportions that only Taylor could have delivered.
2. “You Belong With Me” from Fearless
When you think about growing up with Taylor Swift, you think of “You Belong With Me.” It’s country, it’s pop, it’s full of classic high school imagery and it has an infectious chorus that you crave singing along to in the car. Anyone who has ever felt unrequited love or felt like an outcast hoping to be noticed by their crush from the bleachers — which, don’t lie, is all of us — can relate to this one. You could be 13 or 33 or 63 and there’s something for you in this song and that, to me, is the magic of Taylor Swift. She can write a song so straightforward, so relatable, so catchy that it feels almost obvious or even easy. Like it’s always been there because it encapsulates such a universal feeling or experience. But it’s not easy and it hasn’t always been here, because it could only come from Taylor. It’s her gift, and she’s giving it to us in its purest form here.
1.”All Too Well (10-Minute Version) (Taylor’s Version)” from Red (Taylor’s Version)
Could it be anything else? “All Too Well” has always been Taylor’s magnum opus, the fan-favorite “if you know, you know” ballad that represents her songwriting mastery. It’s her greatest feat in songwriting — and I’m just talking about the original 5-minute version. The lore around this song since its original release was that a version once existed that was double in length. There was more to the story, and she gave it to us when she re-recorded Red nine years later in 2019, and boy did it deliver. In some ways what makes “All Too Well” so special is that, in addition to being so distinctly Taylor, it also feels like a song that you can only truly, fully appreciate if you’re a real fan. “Blank Space” and “You Belong With Me” and “Love Story” are bops that conquered the world; they’re songs that you could imagine pretty much everyone on earth knowing. But “All Too Well,” with its Swiftian storytelling and imagery, is for us. Not an exclusive us, but an us that feels connected to one another through Taylor. Anyone can be part of that, but you have to want it. It feels earned and unique, bathed in refrigerator light, wrapped in a red scarf and paralyzed by time that won’t fly. With “All Too Well,” Taylor proved that she understands the human experience and can harness the complexities of love into song better than almost anyone else — and we’ll remember it like a sacred prayer, all too well, for the rest of our days.
