Taylor Swift Album Rankings

“Wow, that was really well written. I don’t even care about Taylor Swift and I enjoyed this” -My cousin Maya (misquoted for dramatic effect)

I’ll never claim to be a Swiftie, because they scare me. There’s a ride-or-die nature to those kind of fans that I just can’t get behind because being ride-or-die means losing objectivity. And I never want to lose objectivity about Taylor Swift because she’s objectively fascinating. Her career and public image have intersected with sexism, racism, ageism, mental health, arrested development, eating disorders, sexualization vs innocence, commodification vs privacy, the list goes on.

I never want to lose objectivity, and objectively, she’s put out a lot of really good music. So before I see her concert (!!!), I wanted to revisit all the music she’s released. That of course led to me having a lot of thoughts about the music she’s released. The following is the edited version.

10. Reputation

Although conversations about the relationship between Taylor Swift and the media are endless, they are also perpetually one-sided. The media is unfair to Taylor Swift. True. But. That’s how the media feels about Taylor Swift. How does Taylor Swift feel about the media?

Taylor Swift desperately wants to be liked. And of course she does. Normal people want to be liked. Singers who depend on being liked in order to make money really want to be liked. And singers who started their careers as teenagers and had fans chanting their names while their brains were still being molded into shape, need to be liked. And her misery from the current state of her reputation, and her desperation to get that love back, permeates every track on this album.

But wait, says a man who’s never made art before. Doesn’t the best art come from misery? And I say, to this person who thinks artists don’t deserve happiness… sometimes.

When an artist uses their art as a tool with which to explore their misery, and therefore their own psyche and state of self in the moment, they can produce work that is at the same time deeply personal and infinitely relatable (see: “All Too Well”).

That’s not what reputation is. It’s not introspective. It’s out-trospective. It’s trend chasing, throwing everything at the wall, do you like this? Do you like that? Is this enough? No? How about more?

Taylor became a superstar by being true to her own perspective. She sang from the perspective of a teenage girl doodling on her notepad while staring out the window, when most teen pop stars sing from the perspective of “I’m sexy and go to parties I promise I’m a real person and not what the forty-year-old man who wrote this song masturbates to.” Eventually, she would find her own perspective again. And hopefully, we will never return to this.

Favorites: Getaway Car, Endgame

9. 1989

God curse the day Taylor Swift met Max Martin.

I’m not sure how much I can say about this album, which tells you why it’s at the bottom of my list. It’s not as outwardly terrible as reputation, but it’s not good either. It can’t be, because instead of trying to be good, it tried to be popular. And in the process, they created an album full of perfectly serviceable pop songs that could have been sung by Selena Gomez or Katy Perry or Ariana Grande to about the same effect.

Favorites: Style, Wonderland, New Romantics

8. Lover

Aaaaaand just three albums into the list and we’ve already reached albums I genuinely like. Congrats!

This album is at the bottom of the “good” list mostly because I liked it a lot more when it came out than I do now. A lot of that is due to context. This album came after 1989 and reputation, neither of which, obviously, I particularly cared for. It was such a relief to like Taylor Swift again. I thought I had left her behind, a part of my childhood I had outgrown. How incredible that I was wrong.

Now that the relief has faded, and Taylor Swift the Artist seems to have once again emerged after defeating Taylor Swift the Personality, this album seems like less of a miracle. Three more have followed, each Album of the Year contenders (note: Folklore did win) (note 2: Evermore lost to Jon Batiste’s We Are) (note 3: I wish Evermore had lost to Montero).

I’ll zoom in on one song in particular, because it’s both very important to me, and I think indicative of the album as a whole. “The Man” was an absolute revelation to me when I heard it for the first time. There have been so many female empowerment anthems, all of them insufferable. Keep your chin up girl, keep moving, don’t sit still look pretty, etc etc. “The Man” was the first female empowerment song I ever heard that said, I am keeping my chin up, I am working hard, and I’m still not getting what I deserve. And it’s because I’m a girl. Until I heard “The Man,” I didn’t realize how all those girl empowerment anthems were not just cheesy, but actively complicit in the power dynamic they were seemingly criticizing, because they put the onus on the girl. If you’re not getting what you want, work harder! Stay positive! Keep smiling! “The Man” said, fuck smiling, I’m working much harder than people who have way more, and it’s not my fault.

But now that I’ve had all those revelations and worked through my assumptions… I kinda don’t want to listen to “The Man” anymore. Because as a song, it has a weak hook and weak beat and production. All in all, “The Man,” and the album as a whole, are much more valuable as a relic of their time and context than they are as artistic works on their own.

Favorites: Cruel Summer, Paper Rings, Daylight

7. Speak Now

I debated for so long whether Speak Now should be higher or lower than the eponymous Taylor Swift. Here’s what settled it for me: what were the Eras of Taylor Swift? Fearless was the Era of Teenage Fantasy, Red of Vivid Heartbreak, reputation of Mechanical Desperation. And Speak Now was the era of… purple?

Perhaps Speak Now doesn’t have as much of its own identity because it’s tonally and subject-wise much more scattered than the average Taylor album. In-the-moment love songs are still the main dish on the menu, but she also spends a fair amount of time lamenting growing up, spinning fantasies, and attacking mean girls. She’s earnest, and then she’s vicious, and then she’s nostalgic, and then she’s saccharine, and then she’s contemplative. Individually the songs have their merits, but I’m not sure the album as a whole is really as about something as all the others are.

That being said, Speak Now has some of the most beautiful, powerful, sweeping songs in the Taylor canon. “Haunted” makes me feel like I’m screaming into a storm from the top of a mountain. “Enchanted” makes me feel like I’m spinning in a gorgeous dress in a vast candlelit ballroom. This is a transitional album, with maturation on her previous themes and introductions to musical styles she would spend more time on in the future.

Favorites: Back to December, Dear John, Enchanted, Haunted

6. Taylor Swift

When I asked friends if they thought Taylor Swift or Speak Now was the better album, they often told me, “’Speak Now,’ because it’s more mature.” But where is it written that maturity is inherently better?

The Taylor-inspired album Sour (Olivia Rodrigo) makes me feel like I’m babysitting a fourteen-year-old. I listen to Taylor Swift, and I am that fourteen-year-old. I’m back in the passenger seat of my mom’s car, caught in a tidal wave of emotions that aren’t particularly deep, but still the strongest I’ve felt so far. The singles from this album are simply classic, emblematic of an era. I love “Haunted” with every inch of my being, but the opening lines of that song will fade from my memory long before I ever forget “I was riding shotgun with my hair undone in the front seat of his car.”

So instead of blindly accepting that maturity is preferable to naïveté, let’s celebrate the kids we were, and everything that felt possible in the way back when. Isn’t it wonderful that, seventeen years and ten albums later, some of her best songs are still the ones on the very first.

Favorites: Teardrops on My Guitar, Picture to Burn, Should’ve Said No, Tied Together with a Smile, Our Song

5. Fearless

Let’s start with the songs I don’t like. The condescension of “Fifteen” was hard to listen to when she was a nineteen-year-old singing it. Hearing her sing it at age thirty-two is cringe to the extreme. And… yep. That’s about it.

Seriously, I kept listening to the album waiting to hear a song I didn’t like. And it just never came. If we really wanted to stretch it out, the piano version of “Forever and Always” doesn’t really work. It’s an angry song, so stripping it down to a pretty version accompanied by piano feels really incongruous. But my dislike of that song mostly stems from how much I like its original version. So yeah, twenty-six songs on this album (including everything on the re-release), and I only actively dislike one and a half of them.

With simple yet descriptive lyrics, captivating hooks, and seemingly effortless country/rock/pop production, Fearless is an album easy to lose yourself in. It was Taylor’s first Album of the Year win, and at the time she was the youngest artist to win it (beaten by Billie Eilish in 2019, when she was seventeen). As has become par-for-the-course with Grammy wins nowadays, her win was immediately met with backlash, questioning if this country album from a pretty blonde teenage girl really deserved all the accolades. Show me an argument for “no” that isn’t based in sexism, and I will happily listen.

Favorites: The Way I Loved You, Fearless, Jump Then Fall, Come in With the Rain, The Other Side of the Door

TIED: Folklore/Evermore

Call this a copout if you want, but I have absolutely no wish to decide which of these albums I like better. Folklore and Evermore are really two parts of the same album anyway. Sisters, if you will. And everyone knows you don’t pick a favorite sibling. 

When Taylor retreated into solitude during 2020 (yay for money), she used the time to hone and develop her talent as a detail-oriented storyteller. From my perspective, this is when Taylor Swift really grew up. Yeah, she was twenty-nine. So what? It’s earlier than most of you.

All her attempts to show her maturity prior to these albums stumbled or fell flat because the emphasis was on proving her maturity to outsiders, rather than taking the time to get to know herself. The cancellation of the Lover tour interrupted her endless audience-facing routine, and gave her time to just be with herself.

And with that time to herself, she decided to not focus on herself at all. For the first time in a good while, she wrote songs that weren’t explicitly based on her own experiences. And like James Baldwin traveling to Paris or Neil Gaiman going back to London, time away from home can bring more peace and understanding than single-minded self-centered focus does. “The Last Great American Dynasty” is not about Taylor Swift. It’s about a woman who committed the crime of having fun in her youth and in her relationships and faced endless scrutiny for it. It was not about Taylor Swift.

There are so many highs of artistic creativity spread across these two albums. The love triangle of “cardigan,” “august,” and “betty,” three songs that are emotionally, lyrically, and musically rich on their own, but deepen further when put in conversation with each other. “this is me trying,” which stilled my heart long before my head really understood what it was about. “’tis the damn season,” which told the history of a relationship in just the first line. And delivering three different plot twists in three different choruses with the exact same line in “no body, no crime.” The Folklore era proved to me that, even if she had never become famous, even if she had never sold a single song, even if she worked in a Pennsylvania law office as a paralegal, she would still be taking time out her days to sit down and write a song.

Folklore Favorites: this is me trying, august, betty, peace, the lakes

Evermore Favorites: ‘tis the damn season, no body, no crime, ivy, cowboy like me, long story short

2. Red

This album was so well titled first of all. Red. One syllable. Ends on a hard consonant. Vibrant. Defiant. Strong.

Listening to this whole album (especially the re-release with all its added tracks) is like tumbling through a kaleidoscope, trying your best to avoid colliding with the jagged edges of colored glass. It’s heartbreaking, and brutal. By the time I got to “Better Man,” track 22 of 30, my brain had started flashing that Simpsons meme, “Stop! He’s already dead!” 

This album spans genres, opening with the stadium rock anthem “State of Grace,” and closing with the singer/songwriter confessional “All Too Well (10 Minute Version),” with detours through true pop, country, and (regrettably), dubstep. The album uses its different genres to viscerally convey different emotional places in her relationship journey. There are songs for the big gestures, the moments of quiet, the squabbles, and the devastation. And they’re just good.

Favorites: Treacherous, All Too Well, The Last Time, Come Back… Be Here, Message in a Bottle, Forever Winter, The Very First Night

1. Midnights

Y’all I was so sure Red was going to be number one. And in a lot of ways, maybe it still should be. It’s certainly the most impassioned album, and numbers-wise there are a lot more songs on Red that I listen to over and over again than there are on Midnights (although maybe that’s just because there are literally thirty songs on Red Taylor’s Version. Jeez girl).

I have to put Midnights at the top though, because not only is it an artistic achievement in its own right, it also recontextualizes all the albums that came before. So maybe reputation sucks. But the time she spent on that album gave her the experience to know what about that album worked for her and what didn’t. Make the production more minimal. Bring in lyrical detail. Position herself on the high ground rather than getting down in the dirt with her denigrators. And now we have “Vigilante Shit.”

The artistry on this album is so versatile, reaching into themes and styles from the past and melding them together into a sound all her own. I remember in her Long Pond documentary, she talked how she’d been trying to write a song about getting away from everything for a long time. Finally, she was able to write the song by focusing on getting away with someone, and created the lush, poetically crafted ballad “the lakes.” On Midnights, she returned to the idea of escaping the crowd with someone she loves, but reshaped it into the upbeat, lyrically detailed pop song “Paris.” And upbeat, lyrically detailed pop songs are much harder to write than lush, poetically crafted ballads. Seriously. Try it.

Taylor’s greatest strength has always been her lyricism. Somewhere in the pursuit of more popular music stylings in 1989, reputation, and even Lover, lyrical details were either dumbed down to fit the genre, or lost in the loud production. In Midnights, the lyric styles and music styles uplift each other, creating pop songs catch the ear, but then hold the mind.

Midnights is, ultimately, a case for letting pop stars grow up, which we don’t really do as a society. For girls or boys, really. Grow up doesn’t mean, “allowed to talk about sex now.” It means, “Given the time to mature.” “Given the time to make mistakes.” It makes me want to be nicer to those albums and songs I don’t like. Not so much that I scroll upwards and edit what I’ve already written about reputation/1989/etc., but I now recognize them as part of the artist’s developmental journey. And if I can be kinder to that era of Taylor Swift, I can be kinder to other artists who I see going through artistically awkward phases. And I can be kinder to myself. “Doesn’t the best art come from misery?” asks the man who’s never made art before. Yes. With time. And grace.

Favorites: You’re on Your Own Kid, Maroon, Midnight Rain, Mastermind, Paris, High Infidelity, Would’ve Could’ve Should’ve