We’re all too ready to have the discussion of a lifetime: what are Taylor Swift’s best songs?
With the release of Red (Taylor’s Version), we are once again reminded of the timeless genius of Taylor Swift. As a hit singer/songwriter from the age of 15, Swift has released hit after hit with nine studio albums, six EPS, countless live recordings and published compilations, and now intends to re-record all of her albums from Taylor Swift to reputation in order to regain control over her masters. Fearless (Taylor’s Version) was released in February 2021 to much critical praise, and Red (Taylor’s Version), released on November 12th, has elevated the original Red from a genre-transitional album to an instant no-skips classic.
For years, fans of Taylor Swift have been ranking and re-ranking her music. Everyone has a favorite album, a favorite single, a favorite collaboration with another artist. As Swift has deftly navigated genres from country to pop and alternative (and we have a treasure trove of hundreds of songs to choose from) comparisons can be extremely difficult and certainly subjective to a point.
Here is a vague set of criteria for the following list:
- Risks taken: in genre, vocally, or thematically.
- Do the rhythms and syllable counts generally match the tone of the song; do her lines flow lyrically? (Love you, Miss Swift, but you do occasionally have a tendency to cram too many words into one sentence.)
- Is it unique to her discography?
- Do the vocals match the tone of the song?
- That special T. Swift je ne sais quoi! (Specificity, the personal touch, an exceptionally good metaphor about the state of the youth, etc.)
Although Swift has not completed her re-recordings, all “Taylor’s Versions” will be used in lieu of the originals, as per her request, in this list. While the original Fearless and Red albums are masterpieces in their own right, it’s important to honor the creative decisions of their creator.
From one fan to another, please humbly accept these top 13 songs as an act of love, not as a definitive measure of enjoyment. Now, let’s Begin (Again).
13. “Love Story (Taylor’s Version)” – Fearless (Taylor’s Version)
This is probably what most people think of when they think “Taylor Swift.” One of Swift’s first blockbuster hits that initially put her on the map, “Love Story” was famously written when Swift was a teenager and got upset with her parents when they didn’t like a boy she wanted to date…so she went upstairs and wrote the song in a matter of minutes. “Love Story (Taylor’s Version)” has all the bright ecstatic joys of the original—sappy romantic lyrics, expressive vocals so joyful you can almost hear her smiling in the final booming key change—plus the benefits of 30-year-old Swift’s better diction and breath control. I, myself, looped it five times in a row the night it was released and sobbed ecstatically on the floor of my apartment. It’s a nostalgic delight.
Best moment: (bridge into final chorus) “Is this in my head? I don’t know what to think / he knelt to the ground and pulled out a ring and said, / ‘Marry me, Juliet! You’ll never have to be alone. / I love you and that’s all I really know. / I talked to your dad, / go pick out a white dress. / It’s a love story, baby just say yes.’”
12. “Enchanted” – Speak Now
One of Swift’s most indulgently romantic tracks, “Enchanted” is a magical story of falling in love at first sight. “Enchanted” has an incredible build of momentum from the beginning, which is much more muted and acoustic, to a sweeping final declaration of infatuation. Swift’s vocal growth from the beginning to the end of the song is almost addictive, as you hear her desperation build with the lyrics and increasingly intense instrumentals. Each chorus adds a layer—a new set of lyrics in the second chorus, and an additional harmony for the end.
Best moment: (bridge into final chorus) “Please don’t be in love with someone else, / Please don’t have somebody waiting on you. / This night is sparkling, don’t you let it go. / I’m wonderstruck, blushing all the way home. / I’ll spend forever wondering if you knew…”
11. “This Love” – 1989
1989 was Swift’s first pure pop album, and while it certainly has some over-produced moments, “This Love” was a reassuring reminder of her deft control over language. This soaring pop ballad pours out of Swift like a wave, reminiscing on the life, death, and “resurrection” of a relationship through an extended water metaphor. The breathy vocals are mixed with a slow, echoey instrumental that perfectly captures the ache of remembering lost love.
Best moment: (chorus) “This love is good, this love is bad, / this love is alive back from the dead, oh, oh, oh. / These hands had to let it go free, and / this love came back to me.”
10. “Paper Rings” – Lover
When it comes to rankings of Taylor Swift’s songs, the brutally honest, slow ballads tend to top the lists. “Paper Rings” is the truly exceptional, magnificently specific, enthusiastic ode to love. There’s an almost swing-ish/1980s vintage pop sound on this track, coupled with giggly contemporary lyrics like, “The moon is high, like your friends were the night that we first met / went home and tried to stalk you on the internet,” that create a giddy image of the mundane aspects of modern relationships. You can almost hear the laugh in Swift’s voice as she sings.
Best moment: (chorus) “I hate accidents, except when we went from friends to this. / Uh huh, that’s right, darling, you’re the one I want / in paper rings, in picture frames, in dirty dreams. / Oh, you’re the one I want.”
9. “betty” – folklore
folklore was a noted departure from Taylor Swift’s catalogue of deeply personal works. The Grammy-winning album, and its Grammy-nominated sister, evermore, explore many original stories from Swift’s imagination. Notably, a narrative trio exploring the love lives of three fictional high schoolers: Betty (“cardigan”), Augustine (“august”) and James (“betty”). In “betty,” Swift sings from the point of view of a teenage boy who cheated on his girlfriend. It’s unique to her discography in that it marks, to date, the only love song she’s sung to another woman. “betty” proves Swift has maintained her ability to tap into past childhood insecurities even in adulthood (to the great benefit of her music) as she combines a distinctly teenage voice with the elevated language and steady rhythms of her 30-year-old lyrical and vocal talents to create a folk song that’s equally youthful and sincere.
Best moment: (chorus) “But if I just showed up at your party / would you have me? Would you want me? / Would you tell me to go f*ck myself, / or lead me to the garden?”
8. “Delicate” – reputation
If “Untouchable” is a calm prayer to your lover, “Delicate” is a frenetic, hushed whisper to your crush. The intentional lyrical uncertainty, rushed repetition of “Isn’t it? Isn’t it? Isn’t it?” in the chorus, and steady percussion make “Delicate” the perfect ode to romantic insecurity. It captures that feeling of living on the line of an undefined relationship. Swift’s whispered vocal performance matches the lyrics with incredible emotional precision.
Best moment: the pre-chorus to the song that helped give the album its title: “This ain’t for the best / my reputation’s never been worse / so you must like me for me. / We can’t make any promises now, can we, babe? / But you can make me a drink.”
7. “the last great american dynasty” – folklore
This was Swift’s first true country track since Red. “the last great american dynasty” is the story of Rebekah Harkness, an arts patron and socialite Swift became fascinated with after buying Harkness’s Rhode Island mansion “Holiday House.” It’s a classic country narrative, telling the story of Rebekah’s life and how she was shunned by the old money neighborhood she moved into after marriage, and eventually comparing her experience to Swift’s own rise to fame and sense of social isolation to round out the final verse and chorus. The specificity of detail and tongue-in-cheek vocal delivery make this track unique even among Swift’s country songs.
Best moment: (bridge & chorus) “Fifty years is a long time / Holiday House sat quietly on that beach / free of women with madness, their men and bad habits / and then it was bought by me. / Who knows, if I never showed up, what could’ve been? / There goes the loudest woman this town has ever seen. / I had a marvelous time ruining everything.”
6. “coney island” (feat. The National) – evermore
I agonized for weeks over whether or not collaborative tracks would be allowed on the final list and eventually caved on quality alone. “coney island” is an underrated track off of evermore, exploring the ache of reminiscing on a relationship. Swift and collaborator Aaron Dessner wrote a magnificently poetic and simultaneously banal exhumation of a breakup, allowing Matt Beringer of The National to play in a vocal call-and-response with the woman’s voice, as both parties in the relationship realize they’ve been reliving what was lost. The rhythms and instrumental arrangement of the song stay in perpetual motion as the chorus plays “over and over / lost again with no surprises / disappointments, close your eyes and it gets / colder and colder / as the sun goes down” with an unrelenting forward momentum. The lyrics glitter with intimate references to the lost relationship that paint a specific and magical picture, capturing Swift’s best songwriting tendencies all in one piece.
Best moment: tie between (verse) “And do you miss the rogue who coaxed you into paradise and left you there? / Will you forgive my soul when you’re too wise to trust me and too old to care?” and (chorus) “But I think that I forgot to say your name / over and over. / Sorry for not making you my centerfold.”
5. “I Bet You Think About Me” (feat. Chris Stapleton) (Taylor’s Version) (From The Vault) – Red (Taylor’s Version)
I bet you didn’t expect a brand new song this high up on here, huh? Neither did I. “I Bet You Think About Me” is a wickedly smart, Dolly-Parton-esque country breakup song cut from the initial release of Red. The duet takes a scalpel to the elitist tendencies of the ex Taylor sings about, with a twang-y vocal performance that lets the bitterness and humor of the heartbreak eke out. It features some of Swift’s funniest, most clever lyricism to date in its outro: “I bet you think about me in your house / With your organic shoes and your million-dollar couch / I bet you think about me when you say / “Oh my god, she’s insane, she wrote a song about me” / I bet you think about me.” This duet creates the perfect marriage of Swift’s personal experiences and lyrical specificity. Combined with killer folk harmonies from the beautiful voice of Chris Stapleton, what could be better?
Best moment: (chorus) “But now that we’re done and it’s over / I bet it’s hard to believe, / but it turned out I’m harder to forget than I was to leave, / and I bet you think about me.”
4. “Clean” – 1989
“Clean” is a deeply cathartic portrait of self-discovery after a relationship. Using a rainfall metaphor, Swift wields precise lyricism to dictate the pruning of old behaviors to allow for the growth of new ones. What makes “Clean” so special is its perfect match in production sound to theme—the instrumental track and percussion create an almost drip-like rhythm that can go from quiet rumbles to a flood of emotion for the final chorus. The song also contains one of Swift’s shortest bridges (typical for a pop song), while still maintaining the lyrical and thematic specificity that keeps her a cut above the rest.
Best moment: (bridge) “Ten months sober, I must admit / just because you’re clean, don’t mean you don’t miss it. / Ten months older, I won’t give in / now that I’m clean, I’m never gonna risk it.”
3. “Blank Space” – 1989
The best of Swift’s “eff the media” songs, “Blank Space” is a clever and funny parody of the tabloid’s persona of her as a man-hungry femme fatale. Not only is the song undeniably catchy, but it solidified Swift’s transition to pop with its quick wit and clean, belting vocals. The tongue-in-cheek nature of the song means it’s easy to listen to again and again to look for lyrical winks. Its upbeat sound draws the audience in; it sounds like a simple pop anthem the first time around, and reveals a greater depth the closer you listen. For many fans, “Blank Space” was the first song that expressed such a range of humor and maturity beyond the youthful romantic themes that occupied Swift’s earlier albums, and for that, it is exceptional as a turning point in her musical career.
Best moment: tie between (verse) “Keep you second guessin’ like / “Oh my God, who is she?” / I get drunk on jealousy. / But you’ll come back each time you leave, / ’cause, darling, I’m a nightmare dressed like a daydream” and (chorus) “Got a long list of ex-lovers, / they’ll tell you I’m insane, / ’cause you know I love the players / and you love the game.”
2. “Dear John” – Speak Now
(John Mayer should run before Speak Now (Taylor’s Version) drops.) “Dear John” is a brutal manifestation of heartbreak, told from the perspective of a 19-year-old Swift who had just stopped dating a 32-year-old (yes, you read that correctly) John Mayer. Once idolizing the singer for his own music, Swift penned her breakup pains into a delicate and complex country ballad that put her on the map as a bold writer fully embracing her personal life in her art. The song is a 6 ½ minute aching manifesto of loss of innocence that is guaranteed to bring you to tears with its searingly personal lyrics: “Dear John, I see it all now, it was wrong. / Don’t you think nineteen’s too young to be played by your dark, twisted games / when I loved you so?” Swift accompanies her excellent writing with one of her best early vocal performances, belting with raw emotion as the song comes to a climax before the last chorus, then settling down to a simmer for the final “Don’t you think I was too young? You should’a known.”
Best moment: (bridge) “All the girls that you’ve run dry have tired lifeless eyes / ’cause you burned them out, / but I took your matches before fire could catch me / so don’t look now. / I’m shining like fireworks over your sad empty town…”
- “Tim McGraw”
- “Our Song”
Fearless (Taylor’s Version)
- “White Horse (Taylor’s Version)”
- “Untouchable (Taylor’s Version)”
- “Back To December”
- “Last Kiss”
Red (Taylor’s Version)
- “Nothing New (feat. Phoebe Bridgers) (Taylor’s Version) (From The Vault)”
- “New Year’s Day”
- “Death By A Thousand Cuts”
- “exile (feat. Bon Iver)”
- “right where you left me”
1. “All Too Well” (Taylor’s Version) & “All Too Well” (10 Minute Version) (Taylor’s Version) (From The Vault) – Red (Taylor’s Version)
What is there to say about “All Too Well” that hasn’t already been said? Commonly accepted to be Swift’s finest work of all time, “All Too Well” is a romantic autopsy of a relationship past, marked by fleeting memories that fly by in a whirlwind of cutting lyricism. Originally released on Red, there was something about this track, not released as a single, that captured the hearts of Swift’s fans. Maybe it’s the unrelenting personal nature of the lyrics that make them like little clues to pick up on to build a narrative; maybe it’s the way she sings the word “refrigerator”; maybe it’s the bridge with one of Swift’s first ever allusions to sex, opening up a whole other world of hurt. “All Too Well (Taylor’s Version)” is clean, utter perfection, taking you from the beginning of a relationship viewed through rose-colored glasses to the painful split, to the soft bruise of remembering.
“All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault)” is another beast altogether. While the original cut is by far the better song, the 10-minute version offers a fuller narrative complete with new, magnificently cutting lyrics. While it still contains some of Swift’s more awkward songwriting tendencies (I know everyone loves the “‘F*ck the Patriarchy’ keychain on the ground” line, but cutting a sentence between two lines of a song is just a little clunky when we know the type of expert work she’s capable of), the raw emotional value of phrases like “You said if we had been closer in age, maybe it would’ve been fine / and that made me want to die” elevates the song to a flush of intimacy and emotion. It’s the perfect bookend of Red (Taylor’s Version), offering a complete picture of a complicated phase in Swift’s life.
I’m partial to the acoustic “All Too Well (10 Minute Version) (Sad Girl Autumn Version) – Recorded at Long Pond Studios.” Swift delivers a much more personal and delicate performance of the song here that’s fitting to the slow, reminiscent nature of the long version of the song. This is the one that will make you ache. Also for consideration—“All Too Well: The Short Film,” which, more than just a music video, adds a clear narrative and dialogue to an already emotional media experience. If anything, the massive difference in story and tone between the two cuts of “All Too Well (Taylor’s Version)” speaks volumes to Swift’s songwriting brilliance.
“All Too Well (Taylor’s Version)”: “But you keep my old scarf from that very first week / ‘cause it reminds you of innocence and it smells like me. / You can’t get rid of it / ’cause you remember it all too well. / ‘Cause there we are again when I loved you so, / back before you lost the one real thing you’ve ever known. It was rare, I was there / I remember it all too well.”
“All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault)”: “You who charmed my dad with self-effacing jokes / sippin’ coffee like you’re on a late-night show, / but then he watched me watch the front door all night, willin’ you to come, / and he said, ‘It’s supposed to be fun — turning twenty-one.’”
Swifties, I offer this list to you with love. We’re all just happy, free, confused, and lonely at the same time, so please take all of my analyses with a grain of salt.