Taylor Swift 50 Best Songs: “I’m doing fine, I’m on some new shit,” Taylor Swift quietly said at the start of “Folklore,” and no pop songwriter speaks more truthfully. Since her last tour, Swift has released six albums, four of which were new and two of which dug into her archives and proved she’s even more of a steady song fount. New stuff is her brand—maybe her compulsion—and our delight.
So sometimes it takes a special occasion to peel yourself away from the chronic relistenability of “Midnights” to ask: What do “Speak Now,” “1989,” “Reputation,” et al. have to say to me today? On Dec. 13, Swift turns 33. The best song lists are fun to make during celebrations. In celebration of her age, a 13- or 33-song selection would have been suitable and lucky. Given her 225-plus song collection, even narrowing the best selection to 50 is difficult, so we stopped there.
If your favorite Swift song isn’t on this subjective, critical 50-best list, it’s certainly in our unspoken 51st or 52nd spot. Know that on any given day, the winds might have blown differently and we might have put “Shake It Off” or “Love Story” on the list. There were too many great deep cuts to let the major hits dominate the canon for now. I included some songs from “Midnights,” the album of the year, on this “Eras” list. Ready? Boom!
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Taylor Swift 50 Best Songs, Ranked
1. You Belong With Me
It’s as teen-centric as anything Taylor Swift has ever written, but that doesn’t mean you should outgrow it. Life beyond high school has plenty of parallels to “friend-zoning” in your social circle. Who among us ever stops wishing that the person who can’t take their eyes off the cheer captain would actually see us for who we really are? Whether it’s our boss, our peers, our distracted spouse, or an apparently indifferent deity, we all have that one person in our lives who we wish would see us for who we really are. We persevered to the bitter end, like boats fighting a strong river and getting swept back and back into the stands.
Has there been anything in the past fifteen years that can compare to the monstrosity of this? Swift’s inclusion of extra, melodically weird lines in the second verse (“What you doing with a girl like that? What you doing singing in a key like that?”) only serves to skillfully set up the return to the chorus, which is the most rousing of any song written in the twenty-first century. Everything we as humans want and strive for is compressed into a song about removing one’s glasses so that the neighbor’s youngster may see that you’re cute.
Amid all the more complex work she’s done since, her debut, career-launching track stands out as a welcome throwback to simpler times. Its endearing quality, however, continues to reflect the way in which music is more than just background noise; it is a spiritual companion to the moments of our lives. The originality of the idea was in its assertion that a couple may share not only an “our song,” but also “our artist.” That someone of Tim McGraw’s stature and fame has been chosen for the role is a blessing. If teenage lovers had found common ground listening to Big & Rich, we would not feel as sentimental about this 2006 hit.
24. You’re on Your Own, Kid
Swift successfully concedes in this childhood genesis narrative for her ambition and independence that unresolved childhood loneliness and rejection form the greatest breeding ground for uber-driven superstars. That she depicts these quiet, almost steely moments of self-realization with such casualness makes them all the more powerful. (Towards the end of the “Midnights” album, in the song “Mastermind,” she briefly returned to the same topic; it was reminiscent of a theatrical moment when the main theme is briefly reprised.)
Swift elevates a casual backstage meeting with the indie-pop musician she secretly adored to the level of a fairytale climax at a royal ball. If you’re not a hopeless romantic, you might still be swooned by the way she describes what seems like classic love at first sight (even whether in practice it’s check-his-socials-later-to-see-if-he’s-claimed at first sight). She probably stopped thinking about him the next day, but she got a great example of the power of instant chemistry. (And a scent.)
26. Miss Americana and the Heartbreak Prince
Swift, who was often condemned for remaining silent throughout her early career, has shown an unexpected lack of fear in speaking out about political topics in recent years. (Of course, the fallout from speaking up has been significantly more than the criticism she faced while she remained silent.) Although she rarely addresses current events in her music, her song “Miss Americana and the Heartbreak Prince” became the catalyst for a documentary of the same name that chronicled her political awakening.
This “Lover” song is a parody of the common belief that adulthood is quite similar to high school, except that instead of breaking up with a boy, she’s rejecting the centrist beliefs that led her to believe that the United States will always make the right choices. This is not one of her more emotionally engaging songs, which is to be expected from lyrics that operate solely in metaphor. It’s moving to hear America’s former crown princess express concern that she and the course her country is taking may never again be together.
27. Lavender Haze
It’s hard to conceive that anyone who heard “Tim McGraw” or “Teardrops” when it came out could have predicted that one day Swift would be railing against “the 1950s garbage they want from me” and praising the sensuous delights of a relationship that is just cozily what it is. To begin “Midnights,” the song “Lavender Haze” features a rhythm that is almost too chill to be considered R&B, yet the same could be said of a lot of the best subtle R&B. The song has all the hallmarks of Swift in a comfortable rhythm.
28. ‘Tis the Damn Season
You can’t have a Christmas playlist without a Christmas song, and you can’t have Christmas without spiked eggnog, so you can guess which one will be on this list. A melancholy one-off (“Christmas Tree Farm”) and, more importantly, this relatively unsentimental homage to hometown ex-sex during the holidays followed Swift’s early Christmas EP many years later, much to the delight of everyone’s customized holiday mixes. We can view this as a creative act, much like the rest of the “Evermore”/”Folklore” cycle (i.e., there is no mention of where the paparazzi are going to go while she and her old classmate briefly reignite some embers just for the hell of it). In contrast, the song’s lived-in quality is reflected in the complexity and realism of the emotions it evokes. “Ho ho sigh” is an informal expression of laughter.
29. Teardrops on My Guitar
Not in the countryside, where she was already well-established before the release of her sophomore album, but on the MTV side, where several “pop mixes” were to follow until she eventually “selected a lane,” as she described it. It may seem archaic now, but a teardrop played on a sincere instrument will never go out of style. (She would quietly do a sequel to this ballad, with record industry officials in place of the much more benevolent Drew, on “My Tears Ricochet,” many years later.)
30. Mad Woman
Many of the darker tracks on “Folklore” can be interpreted in one of two ways: either as songs about ending a relationship or as songs about ending a relationship with Big Machine. The song “Mad Woman” can be interpreted in two ways, both of which are valid. However, if it is one of her personal tunes on the album and not one of the character songs, the unusual intensity with which she writes and sings it suggests that it is more likely about a recent business split than some long-ago bad romance she is dredging up as song fodder.
However, she had to know that some spectators were wondering, “Why can’t she just go on?” because of how openly upset she allowed herself to be in public remarks about what went wrong. Regardless of how you feel about the master sale, you can’t deny her unwavering commitment to the matter. You’ll only drive her crazier if you keep calling her that, she says. When threatened, a scorpion will respond with a deadly “strike(s) and you know I will.” Wow, this is a far cry from slamming screen doors and first or last kisses, and it’s fascinating.
31. False God
With that slinky vibe and the addition of something Swift has never used before—a solo saxophone—this song about a relationship that has progressed for some of the wrong reasons can’t help but feel appropriate. Fans hoped she would go further in this way after she used it for a seductive-sounding second number during an “SNL” performance. Don’t worry, she can talk now.
At some point in their careers, every female vocalist worth her salt should try to write their own version of an Evanescence song. Her third studio album, titled “Speak Now,” has this lavishly orchestrated Goth-rocker from the end of the period in which her voice still had a hint of girlish shrillness. Even if she has improved her singing skills by a factor of one thousand, the quaint nostalgia we feel for her less trained, barely post-adolescent, I-mean-it tones that drove her pained lament to its climax remains.
33. …Ready for It?
We certainly are, or at least we were. This opening track from “Reputation” was also a highlight of the 2018 tour of the same name. Some listeners find its hip-hop-influenced lyrics distracting, and some criticize Swift for singing them in that style. That, however, does establish the tune’s dramatic shifts, as it transitions into a featherweight-sweet and sensual pre-chorus before Max Martin and Shellback drop the hammer again with a recurrent synth riff that sounds like heavy metal. This release is well worth the pause caused by the ellipses.
34. Soon You’ll Get Better
Nearly everyone expected Swift’s collaboration with the Dixie Chicks to be lighthearted, like the murder ballad she later did with Haim. Instead, she broke everyone’s hearts with “Soon You’ll Get Better,” a song about dealing with her mother’s cancer that covered all of the phases of grief (not for death, but for an illness that brings an end to the carefree life a family once enjoyed).
The majority of “Lover” album listeners chose to skip this song, but Taylor Swift should know better. This is something you should only use behind closed doors, even if you are fortunate enough to not have any close relatives who are suffering from a long-term or terminal illness right now.
35. Daylight (Live From Paris)
36. The Last Great American Dynasty
Swift has a soft spot for ladies who society labels as crazy. It’s tough to fathom why, after being maligned for what seems like an eternity during the past decade. She decided to recount the narrative of how she voluntarily isolated herself from society when she bought a mansion in Rhode Island previously owned by affluent socialite Rebekah Harkness in the middle of the 2010s and began to identify with Harkness.
There’s a common thread between songs like “Mad Woman” and “The Lucky One,” an older Swift song that paints a picture of a famous person who gave it all up and found happiness in the wilderness. This is a great bit of character writing, and while it’s not a diary entry like so many other songs by Swift, it may be hinting that she hopes to become a “crazy,” wealthy, and powerful old spinster lady who trades insults with her neighbors over the fence. (Perhaps we shouldn’t tell Joe about this.)
If she already has everything, what do you gift her? In one of the more blatantly honest tracks on her upcoming album, “Folklore,” Swift informs her partner that she is everything from calm. As a result, she may never be able to put the words “You need to calm down” into action so long as she and her beloved are together. Knowing that it concerns a famous couple who is still very much together mitigates some of the warning signs.
But I’m sure there are thousands of other couples out there who can relate because at least one of them has a high-pressure or public job. It’s a touching, though slightly ominous, admission by one lover to another that there is, at times, a cost to paying attention to someone whose way of life, circumstances, or even simply inherent personality type is… a lot.
38. All You Had to Do Was Stay
The sequel to her “I asked just one thing of you: to not depart” series of songs. That one command was illegal, and like Adam in the Garden of Eden, he was expelled when he recognized his error. Melodically, this song could have taken a much more standard route. But in her dream, Swift found herself unable to say anything but “stay!” in an artificially high voice, so she included that effect into the chorus.
It’s typical of Swift to make a choice that sounds risky at first but becomes completely normal and even predictable by the third time you listen to the song. Despite the fact that that is a very entertaining trick, the song’s boldness is what really gets to me. that no matter how much she wished for the relationship to continue, it was over once the guy called it. (This occurs frequently throughout Swift’s work.) That’s some fantastic role modeling for her young, impressionable admirers.
39. I Knew You Were Trouble
The moment Max Martin and Shellback, the producers tasked with modernizing Swift’s sound for a select few tracks on her fourth album, “Red,” walked through the door, we knew they were trouble, good danger. Still, a major player in the production, Nathan Chapman brilliantly directed emotionally raw tracks like “All Too Well” and “Sad Beautiful Tragic,” both of which went on to become classics in their own right. The arrival of our Swedish overlords, however, made it clear that we were no longer in Kansas or any other place where country music is destined to reign supreme forever.
One of the most drastic developments was “I Knew You Were Trouble,” which had dubstep-like elements from an artist who might have safely stuck to dobros. It’s a little dated, but it still stands up; the electronic chorus almost has a violent quality to it, as if it were meant to accompany a woman hurling herself to the floor in frustration after a terrible call with a good-looking man.
Although Swift has a reputation for sincerity, there is some competition for the title of “a funniest song she’s ever written,” I’m going to go out on a limb and say that this is it. As if the lines “Karma is a cat / Purring in my lap ’cause it loves me / Flexing like a goddamn acrobat” aren’t some of the best comedy that anybody has written in any recent year, a few humorless snobs pounced on “Midnights” for its over-the-top declarations of self-satisfaction and cosmic comeuppance.
While it’s true that Swift’s writing might be humorous at times, that doesn’t mean she isn’t also dead serious: This song can be interpreted as a celebration of the change in fortunes shared by the two parties involved. And there’s no doubt in her mind that she thinks history ultimately rewards people who act with integrity. But Antonoff’s brilliant co-production work on this song makes it a gentle banger in its own right. And it’s a fantastic follow-up to “I Forgot You Existed,” as she argues that destiny did not forget.
41. Should’ve Said No
Swift’s best songs after a breakup, especially at the beginning of her career, often just restate the obvious to her exes. It was as simple as staying! You need only reply “no” I mean, seriously, you guys: you were only hired for one task.
42. I Did Something Bad
This can be thought of as a spiritual continuation of “Blank Space.” In that, she was still satirically acting out the role of the evil girl. When she released “Reputation,” she was no longer doing it for laughs. This is an “I could eff you up, seriously” song. The song rocks and could manhandle a stadium as easily as handled a single man, so it’s no surprise that it was a highlight of her 2018 tour.
43. Champagne Problems
A nightmare of chaos that is somehow satisfying. Swift had previously “engaged” in an engagement ring scenario with “Paper Rings” off her album “Lover,” but that song was a lighthearted look into the experience of making a vow when money is tight. This tune represents the polar opposite in every way possible. In her song, the protagonist rejects a plan that would have led to the public proclamation her prospective fiance had promised his wealthy family.
She would’ve been such a wonderful bride / What a shame she’s messed in the mind, and the singer imagines that this has ruined everything for everyone. The last time she wrote a song that wasn’t all about her, she would have performed this one for high musical melodrama. Everything in this story, from the opening lines to the effed-up happily-ever-after ending, is brilliantly detailed and delicate.
44. The Man
Perhaps the most overtly feminist comment by Swift can be considered polemical. There are few forms of propaganda that are either more entertaining or more demonstrably accurate. What’s it like when everyone trusts your word instead of the word of the guy who turns out to be the least dependable narrator in the history of entertainment? wonders the lady who was initially taken at her word. But we’re getting off-topic.
This is more of an “I am every woman” hymn than a memoir, and she does her gender proud with zinger after zinger that you just know is true. Probably the simplest sentence she’s ever written, “If I was a man, then I’d be the man,” features some of the best wordplays she’s ever used.
45. The 1
One tune on “Folklore” that may have been underappreciated is “The 1,” the album’s opener and a quiet little beauty that may easily be missed. How come nobody seems to care about this? Perhaps it is precisely because it is so unassuming that it is so great and such an important element of the Swift canon. She must have offered her listeners dozens of songs whereby the significance of love is equated with that of life and death. Around these parts, the general sentiment is along the lines of “Eh — would have been great to have watched that one through to the end to see how it played out, but no biggie.”
That the woman who made wuthering heights her poetic brand can also gently declare “c’est la vie” and make that work for a terrific song is possibly the ultimate measure of maturity in her writing. But perhaps the woman does not protest strongly enough; the odd chord changes she or Aaron Dessner incorporated into the song suggest a sadness that goes beyond just resignation.
In the meanwhile, I think the title is a musical joke since it is spelled out as a numeral, as a musician would write it, rather than as “the one.” The word “one” slips from the final note of one bar into the first note of the next bar, which is the 1 as the chorus concludes. It’s like a hidden hint that the guy who got away wasn’t the one but also was.
46. Invisible String
The best of Swift’s overtly autobiographical and affectionate love songs; a relatively tiny section of her entire oeuvre considering her predilection for drama, but with good competition. Swift isn’t one to automatically assume the supernatural, but on this beautifully picked acoustic track, she ponders if or not a divine smile is bringing everything together.
The words here felt so blatantly true to life that you already knew her long-term partner worked in a blue shirt at a yogurt store or that one of her famous exes did, in fact, have a newborn kid that would have prompted a gift from her before you even Googled it. That’s a lot of detail to packing into a love song, but the chorus is simple enough that any young couple who believes their futures are bound by something more sinister than chance may sing along.
47. This Is Me Trying
Since being fatigued is not Swift’s normal state, the novelty of this tune lies in the fact that she sounds more exhausted than ever before. In most cases, the phrase “depleted-sounding” would not be used to describe a song in a positive light, but this is an exception. It’s the sound of someone who has decided to spend the rest of their life in a doorway, pleading for a second chance with all the strength they have left but can’t quite muster. Despite its slow tempo, it serves as an anthem of sorts, inspiring listeners with its message of optimism.
48. Out of the Woods
Taylor, can you tell me how many stitches he received? What, twenty? Her tendency to provide minute details—eye color, necklace shape, astrological sign, clothing item street name, or even number of stitches—while leaving fans to make educated or fanciful guesses as to what kind of bigger picture these brushstrokes enhance gives her more autobiographical songs such power. One of the most talked-about songs from “1989” is “Out of the Woods,” and for this song, it’s more important to understand the emotional tenor of the scenario than it is to know with whom she spent the night in the ER.
If you can put aside some of the specifics, the song is about a relationship that has reached a reasonable level but isn’t truly out of the woods yet. In the choruses, she repeatedly tells herself that everything is OK by saying, “excellent!” to the query, “Are we in the clear yet?” This reveals that our protagonist is continually trying to convince herself that everything is fine. The snowmobile came out of hiding, but she stays hidden in the trees for the duration of the song.
49. Illicit Affairs
In many ways, Swift’s “Folklore” album reads like a collection of short stories she wrote. This in-depth exploration of the ethics and mundane particulars of adultery makes it seem unlikely that a famous person could ever engage in the kind of secretive encounters that led to her feeling like such a horrible person. Leave the perfume on the shelf that you picked out just for him / So you leave no trace behind; tell your friends you’re out for a run / You’ll be flushed when you return; Swift must have done some research with friends — or just had that vivid a literary imagination.
Holy crap, chick. This song may seem like a simple list of 50 ideas for finding a romantic partner, but the lyrics are anything but simple. Lyrics like “a fading, mercurial high — a narcotic that only worked the first few hundred times” and “you taught me a hidden language I can’t speak with anyone else” convey a genuine sensation of terror, longing, and self-loathing in reference to an affair. Swift has written a movie’s worth of wisdom about cheating in just a few minutes. It should inspire confidence in what she could do as a screenwriter.
50. Cowboys Like Me
Swift was once a major name in country music, but she has never truly dabbled with country rock. On “Folklore” and “Evermore,” though, where the laconic character of a couple of Aaron Dessner’s, in particular, lent itself to something that seemed a little like the laid-back early ’70s manner, she did a little bit in bits and pieces.
In “Cowboy Like Me,” one of the more obviously fictional stories she was testing, she plays an unsentimental grifter in a vacation region (I’m envisioning Montana) and falls in love with another person who works in the same murky line of non-work. Good thing Taylor doesn’t think “forever is the sweetest con,” and good thing she’s developed as a writer to the point where she can make up a character who thinks that.