There’s no denying the effect Taylor Swift has on her fans, both casual and devoted, as she manages to consistently keep them on their toes, especially in anticipation of new releases. Having announced her upcoming album, Midnights, while accepting an award at the 2022 MTV Video Music Awards, she further cemented herself as one of the most talked about singer-songwriters of her generation.
Having been in the business for over 15-years now and only 32, (her self-titled album debuted in 2006 for all my fellow disbelieving millennials) she’s jumped between genres, mixing country with pop and then something in between with her latest albums folklore and Evermore and demonstrated a savvy if cynical understanding of how women are perceived in the industry and how it necessitates frequent change to keep the audiences focus.
And she’s largely done so, even with some of her more contested albums. An enormously talented songwriter especially when it comes to storytelling (something she’s excelled at since she started) her discography will only continue to grow. With Midnights out October 21, we decided to use math, science, and general witchery to determine the 20 best Taylor Swifts songs. It was trying, but we got there in the end.
Take a look below at her 20 best songs to date (for now.)
20. Delicate, Reputation
Don’t let Swift’s comeback marketing in the form of a black-and-white album cover and tabloids-inspired graphic design fool you. Reputation was always very much another album filled with love songs. (After all, Lover followed in a bright burst of color.) “Delicate’s” release as the album’s sneaky fifth single is perhaps the best evidence that try as she might–Swift did not completely trade away her frustration with the headlines or a celebrity rival whose name rhymes with “best” in her Fall Out Boy and Panic at the Disco!-inspired album. The synth-heavy song makes the early fragility of a new relationship sound exciting, even reverent in Swift’s whispery vocalizing. As an earworm, the intro and chorus are memorable to mouth along to, but the song also offers a true vulnerability to fans about the hopeful first weeks with a new guy, with satisfactory hints suggesting Joe Alywn. [Ingrid Allen]
19. Paper Rings, Lover
Off an otherwise blip of an album, “Paper Rings” escapes the forgettable curse by producing a really sense of fun amidst others that are posturing as such but are actually hollow. Rather than succumb to mundanity, it instead crafts a sweet and soulful number. It’s the best example on Lover of Swifts want to merge the folksy elements of her earlier material with pop refrains and energy with lively refrains. It’s playful and cute and is testament to the singer’s songwriting wizardry to write something so deceptively simple and easy to listen to. [Allyson Johnson]
18. Cowboy Like Me, Evermore
Evermore is by far Taylor Swift’s most lyrically impressive album, the more mature and reflective sister album to its predecessor, folklore. Certain songs of evermore grabbed listeners’ attention early, such as “Champagne Problems” and “Willow,” one song that quickly became a fan favorite was “Cowboy Like Me,” which depicts a love story between two thieves. The two lovers are described as ‘cowboys’ and ‘bandits,’ who are disillusioned with materialistic people and don’t seem to connect with anyone until they meet each other; finding love when they are least expecting it. Swift’s lyrical choices perfectly describe these two lover’s journey together and how they are hesitant to pursue a life together due to their pasts, “the skeletons in both our closets plotted hard to fuck this up,” and the futile nature of relationships, “forever is the sweetest con” But the song ends with them deciding to fully commit to each other, “I’m never gonna love again.” [Alexa Brown]
17. Invisible String, Folklore
Some of the best examples of Taylor Swift’s ability to weave sweet, catchy melodies with simple but relatable lyricism are found in her sedate, stripped-down numbers. Written with producer Aaron Dessner, the two inject classic country elements into the soft number with rubber bridge guitars and finger picked acoustics that create a timeless appeal. Just the instrumentals alone are striking for their stripped down nature – it’s tight and controlled in production yet still comes across loose. It’s a tremendous use of Swift’s lower register as she sings about soulmates who were always destined to meet, tethered together by golden thread. [Allyson Johnson]
16. Style, 1989
Released as the third single off her 1989 album, the song made a splash in the charts peaking at number 1 on the US Top 40. The song is also 3xPlatinum in the US. “Style” contributed to Tayler’s rebranding as a Pop artist from her otherwise country roots. The song was written by Taylor and producers Max Martin, Shellback, and Ali Payami. Lyrics from the song run from memory to memory and contains a confession from Taylor’s POV that she’s also cheated on her partner. Critically, the song was a success, garnering raving reviews from The New York Times and The Observer. “Style” and “Out of the Woods” off of 1989 are both speculated to be about Harry Styles by sleuthing fans. [Isobel Grieve]
15. Mine, Speak Now
One of Taylor Swift’s strongest attributes from the very start of her career has been her ability to tell a cohesive story in just one song. She sets the stage and possitions the perspective of who she’ll be using as her main character for the number and she’s off. This is particularly evident in love songs such as “Mine,” a rallying single that shines a light on the other aspect that’s made the singer such a force to be reckoned with : she can write the hell out of a damn chorus. Like so many of her most-played songs, “Mine” has an infectiously catchy hook and it’s near impossible to not sing along during the chorus – fan or not. [Allyson Johnson]
14. Wildest Dreams, 1989
“Wildest Dreams” is an emotional reminiscence of romance’s past. The atmospheric pop power ballad pulls its listener into the tangled love affair Taylor Swift is singing about. Taylor wrote the song with producers Max Martin and Shellback. “Her” (Tayler’s Version) came out ahead of her 1989 (Tayler’s Version) album while the original song was trending on TikTok. Like most of her work, many fans speculate who of Tayler’s famous lovers the song could be about: due to the imagery of her 2015 music video, the mass majority assume the song is about MCU alum Tom Hiddleston. The song has been used in several movies and TV shows, including an instrumental version in Netflix’s Bridgerton. [Isobel Grieve]
13. State of Grace, Red
A pulsating arena rocker with inklings of U2, “State of Grace” wasn’t the first inkling that Swift was interested in making her version of alternative rock but it was one of her best forays into the genre before she went all in on Folklore. The song’s lyrics are some of her sharpest observations on the positives and negatives of relationships, including the line that Swift herself singled out as Red’s thesis, “Love is a ruthless game unless you play it good and right.” The lyrics aren’t scathing or dismissive, but reflective and nuanced, a sign of what was to come on “Style” and “Wildest Dreams” and Folklore. [Ryan Gibbs]
12. Fearless, Fearless
The lead and title track of her breakout album is a statement of intent, a declaration of upcoming dominance in the singer-songwriter field. “Fearless” is not just a great one-word hook, it’s a word that sums up her career in total. And “In this moment now, capture it” sums up her songwriting method just as well: she’s been capturing moments with an almost photographic clarity for well over a decade now.
The moments she captures here? Going for a drive with her lover, who runs his hands through his hair, “absentmindedly making me want you”. Dancing in a storm in her best dress. Hands trembling in the doorway before her first kiss. Noticing how that same lover “put” his eyes on her – “put” is the carefully chosen, crucial word, which says so much, and with just three letters. No other songwriter could’ve landed on those details, or made them signify so much. And the casual beauty of the song’s production makes all of those moments land all the harder. [Oliver Hollander]
11. Enchanted, Speak Now
An acoustic guitar heavy number, the undeniable youthful naivete is present but manages to add winsome elements to the overall composition. This is especially true with the deftly refined production. Controlled verses builds to crescendos of choruses as they explode into an exuberant display of emotion with the strings adding an added level of whimsy. A songwriter who, for good and bad, has always worn her heart on her sleeve lyrically speaking, in a song like “Enchanted” it only manages to further elevate the emotional pull of its best hooks. [Allyson Johnson]
10. Willow, Evermore
A wistful slice of folk with a memorable guitar hook, “Willow” is filled with one-line analogies and similies (“Lost in your current like a priceless wine”, etc.) that make it one of the best songs on Evermore and proof that the album wasn’t just Folklore B-sides. Even that “come back stronger than a ’90s trend” line often cited as either the best or worst lyric in the song feels like an unmistakably Swiftian turn of phrase, the kind of offbeat line that you can’t ascribe to any writer but her. Maybe the most indie rock Hot 100 number ones since “Somebody That I Used to Know”, “Willow” is cozy, sweet, and memorable and one of the best songs Swift released in 2020. [Ryan Gibbs]
9. Champagne Problems, Evermore
Built around harmonic piano accompaniment and guitar riffs, “Champagne Problems” stands out as a prime example of Swift’s ability to craft compelling minimalist narratives. This lo-fi ballad narrates the story of a broken engagement of college sweethearts, but, in a little more than 280 words, alludes to the impact of mental health in relationships and provides a self-aware commentary on how, amid the convoluted and pandemic-infused world in which her album Evermore came out, this entire situation might seem inconsequential. However, it achieves so without undermining the bittersweet end of the relationship. Her usage of impressionist imagery juxtaposed with specific details such as the brand of the champagne bought in the failed proposal showcases the level of Swift’s narrative-building and solidifies her status as one of the most important songwriters of contemporary music. [Pedro Graterol]
It’s a slight exaggeration to ask who would’ve thought Taylor Swift and Bon Iver would align so well, but both have been dabbling with the others genres for years now and it was but a matter of time before they found a project that sufficed both artists’ sensibilities. The result is the gorgeously emotive and beautifully produced “Exile,” one of those in retrospective breakup songs that deal with the heartache, confusion, and internalized bitterness that comes when a romance sours. Their voices complement one another, Justin Vernon’s in particular are punched up with the difference between his unaltered vocals in the verses to the slightly manipulated ones in the choruses and bridge. Perhaps the strongest element of the song, evocative from the very first minor chords, is the lyrical density not so much in the words used but in how lines are utilized as dialogue, each voice coming in and out as they recount a moment from their relationship differently. [Allyson Johnson]
7. Our Song, Taylor Swift
“Our Song” is first and foremost a cute love story with a nice country-pop melody. The song reminds me why I love Taylor Swift’s debut album: the country, the storytelling, and the romantic lyrics. In “Our Song”, Taylor sings about how she has yet to find the “right” song to describe her and her boyfriend’s relationship. Swift sings how she wrote her song on a napkin to describe their relationship and all of the special moments the two of them share, peeking into moments such as them driving in the car, sneaking out late, and talking on the phone. To think Swift wrote this song when she was only a freshman in high school and released it when she was 17-years-old is incredible. The song captures the essence of a high school romance and is sung with strong vocals and an appealing melody. [Chelsie Derman]
6. August, Folklore
Folklore saw Swift emphasize her lyrics on character studies, particularly in its love triangle trilogy portraying the relationships of three characters; James, Betty, and August. “August” is the middle installment of that trilogy, telling of a romantic encounter between two people who might regret having one. The song’s wistful, summer-by-the-sea setting feels right at home in the center of the cozy Folklore. What makes “August” stick out among the trilogy, though, is its music and melody, a strumming jangle pop concoction that recalls early ‘90s band The Sundays (compare, for instance, “You’re Not the Only One I Know”). [Ryan Gibbs]
5. You Belong With Me, Fearless
The underlying confidence makes this arguably the most purely fun of her beloved singles. I mean, is anyone in any doubt at the end of this song that the girl will one day get her guy? This one was such a huge hit because absolutely everyone can relate to the situation of wanting to belt out “WHY CAN’T YOU SEEEEE?” to a love interest who’s blind enough to only view us as a friend. It’s every teen’s nightmare, the stuff of much screaming into pillows in the dead of night.
Yet Taylor Swift turns it into an expression of triumph, with a singalong chorus to end all singalong choruses, the singing along to of which would make any angsty teenager feel better for a while. Plus, in verses and choruses alike, there’s a confidence to Taylor’s vocals that’s so clear it’s tinged with comedy. It never allows you to doubt for even one second that she IS going to make him see, one day, that they belong together. That’s what makes this pop explosion such a joy, and so easy to get caught up in every time: its assuredness, which stands out because much of the rest of Fearless, and indeed Taylor’s entire songbook, cast multiple shades of doubt on such confidence. [Oliver Hollander]
4. Love Story, Fearless
If there was one song that encapsulates all of Taylor Swift’s old country music, “Love Story”sits at the top of the list. The romantic, breathtaking lyrics come across as magical — holding the charm of a fairytale — as Swift (at least in the music video) portrays a princess with her very own Prince Charming. The song also tells a story — Romeo and Juliet, in particular — and this idea of a forbidden romance. Listening to “Love Story” makes me feel like I’m immersed in a story like I’m the one entangled in a forbidden romance and living in an enchanted castle, using a sweet and catchy melody to make us all feel like we’re a character in her stories. [Chelsie Derman]
3. Blank Space, 1989
“Blank Space” marks the moment I started to listen to Taylor Swift again. My love for this song has more to do with the music video—a video I’ve seen probably a hundred times when it first came out. It’s a masterclass in embracing what the media and the haters have said about you and dialing it up to ten. “Blank Space” the song already references Taylor being “a nightmare” but the video showcases that even more. It’s a great song with a defiant edge an a video that manages to make it even better. ,It brought back one fan—who knows how many else? [Katey Stoetzel]
2. Mirrorball, Folklore
On an album that already managed to set itself apart from all her previous ones, “Mirrorball” stood out in Folklore as a big departure for Taylor Swift. “Mirrorball” captures a willingness to change for someone; however, the mirror motif throughout the song ensures this change is no romantic notion. Its airy quality makes it come across as a breezy contribution to the album but its lyrics point to a darker meaning. [Katey Stoetzel]
Kanye may have claimed to have made her famous (even he must know that’s bullshit), but it’s obvious to anyone who’s listened to Taylor’s catalog that what made her famous was, first and foremost, a distinct melodic genius, and in a close second, a lyrical ability to hone in on exactly the right details to universalize her tales of young women’s loves won and lost. “All Too Well”, a power ballad from Red that originally only reached number 80 on the Billboard Hot 100 (as you probably know, it eventually reached number 1 last year in its 10-minute “Taylor’s Version”), has gradually overtaken her bigger chart smashes to become the song most beloved by the hardcore fanbase, which includes writers for this website because it epitomizes everything she does best.
It has a melody that you’ll remember all too well after only a couple of listens, of course, it does – and Taylor swirls that melody around and chews on it in the most confident vocal runs of her career, plus uses it as a foundation on which to crash the waves of the song’s multiple musical crescendos (she’s never used dynamics quite so brilliantly). And then there’s the words… the words! Every single line is a gem, so casually perfect that you can’t believe nobody else ever thought of them before: “The autumn leaves falling down like pieces into place”, “dancing round the kitchen in the refrigerator light”, “So casually cruel in the name of being honest”, “I’m a crumpled up piece of paper lying here”
There are so many great ones, the whole song could easily be quoted. But it would be better to just listen to the entirety yourself – the 10-minute re-released version if you’re emotionally brave enough, the 5-minute original if you’re not. Either way, it’ll leave you in awe at Taylor’s songwriting ability. And also leave you wondering about that scarf, and how exactly she knows that her ex kept hold of it on purpose, just to remember her by. [Oliver Hollander]