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This is the first article of a three-part series dedicated to analyzing and reminiscing on Taylor Swift’s discography. The second and third articles will be released in the months to come. 

Hi. We’re Andie and Abby, and we are, to put it lightly, obsessed with Taylor Swift, and have been for most of our lives. Taylor was our soundtrack for growing up, and we’re older now (if not all that much wiser). As we head into our senior year of college, we’ve decided that there is no better time to go through Taylor’s discography, album by album, and look back on all her music. 

Revisiting all of this is also prescient as Taylor re-records her catalog. As the result of the contract signed by an ingenuous, idealistic Swift back in 2006 with Big Machine Records, headed by Nashville industry veteran Scott Borchetta, Taylor Swift does not own (and has never owned) any of the albums she produced with the label, despite being its biggest success by a country mile. She tried to buy her masters (the original recordings of the six albums she put out with Big Machine) back from the label, to no avail. Instead, it was sold in 2019 to a company owned by Scooter Braun, the manager of several artists with whom Swift has publicly feuded. Most notable of these artists is Kanye West, who infamously interrupted Taylor’s acceptance speech for Best Video by a Female Artist at the 2009 VMAs and went on to rap crudely about her on his 2016 track, “Famous” (“I feel like me and Taylor might still have sex / Why? I made that bitch famous”) without her permission. Her nude likeness was also used in the “Famous” music video without her permission; Braun was West’s manager throughout this period. 

Swift’s sense of betrayal in reaction to Braun’s acquisition of the valuable asset that is her catalog is understandable, especially given her efforts to buy it back from Borchetta herself and his refusal to sell it to her. So, she’s re-recording everything, with the idea that her re-recorded versions, known as Taylor’s Versions, will replace the originals, thereby de-valuing the asset and taking back control of her art for herself. In doing so, she’s sending a powerful message: Taylor Swift is not a commodity to be bought or sold. She is an artist before and after anything else, and she more than deserves to be taken seriously. 

For an artist like Taylor Swift, the basic requirement of respect has unfortunately been a massive ask. Since the start of her career, she’s been written off by critics and much of the industry as a basic, boy-crazy, hopeless romantic who writes music for young girls and no one else. This is in and of itself an assumption grounded in layers upon layers of misogyny. Taylor’s music portrays incredibly real and intense experiences with unparalleled depth and poignancy. That is no small feat, nor should it be treated as such. 

And that represents only the half of the ridiculous patriarchal regularities that Taylor has had to deal with since coming into the public eye at all of fourteen years old. On top of all of this, Taylor is a victim of sexual assault, and made the indescribably brave decision to take out a very public case. She was then horrifically, publicly ridiculed in the pre-Me Too era for speaking up for herself, and in doing so, for countless others with similar experiences. 

Taylor has been criticized by feminists throughout her career, but so much of Swift’s experience is inherently empowering, from her fight against the man who assaulted her, to taking control of her art back from entitled men who never should’ve had it in the first place. She’s far from perfect, but it’s important to recognize the misogyny that is so inherent in so many of the struggles Swift has faced. 

Despite all of these monumental obstacles, Taylor has put out a wide variety of really great music — she’s a lyrical mastermind with 3 albums of the year under her belt, and she’s not even close to being done. It’s about time we properly go through and recognize her genius. This is the first of a three-part series, because (if you can’t already tell) we have a lot to say about this. Like, a LOT a lot. We’ve grouped her albums into threes chronologically, so today we’ll cover Taylor Swift, Fearless and Speak Now, complete with our analysis and memories; we’ll move through the rest of her discography in the next two articles. 

If you don’t think this series sounds interesting, or worthy of your precious time, you’re exactly who it’s written for. We hope it serves as a wake-up call: show Taylor some damn respect.


Abby: The debut album is rarely anyone’s favorite, but it gets an undeservedly bad rep because Taylor’s discography has a rare kind of depth and quality to it, so we compare it to albums that are just on a whole other level. It’s like comparing the personal statement essay that got you into Michigan with your senior thesis. But Taylor Swift deserves a reputation(haha) as so much more than just the album that introduced us to this artist. Not everyone can get down with country, but it’s important to remember that this album is a solid country debut. Just because it doesn’t match the danceability of 1989 or the storytelling of folklore and evermore doesn’t mean it isn’t good in its own right. It’s just in a different category. 

But as a country album, and especially as a debut country album, this is a good one: it’s well-rounded, easy to listen to, and lends itself to driving around with the windows down (riding shotgun with your hair undone in the front seat of his car, if you will). It’s got the up-tempo breakup anthems (Should’ve Said No, Tell Me Why), the slow-and-sweet songs (Tim McGraw) and hints of the emotional depth we would come to expect from Taylor. Sure, it’s no album of the year, no sellout tour, but it’s a fun country album, and there is nothing wrong with that. 

Andie: I think it’s especially important to note that the debut was a breakout album. Taylor was fourteen when this album was released, and she still, albeit with the help of her team, made a name for herself in the world of country. In order to do that, she had to appeal to an audience used to specific country song elements. And boy, did Taylor lean into it. Take “Our Song” for example, the third single released from the debut that absolutely dominated the charts. The lyrics are filled with quintessential country staples (mentions of cars, mamas, God, and amen), the rhythm is guided by a country band, and her voice carries a sweet Southern twang. 

Taylor carries this energy into the iconic “Our Song” music video, a production filled with platinum blonde curls, cowboy boots, and princess-esque dresses. Even as a brunette six-year-old from the Northeast, I couldn’t help but buy into it. The beauty she emitted combined with the fun nature of the song felt too whimsical to ignore. For a first grader, the video painted the perfect scene of a picturesque relationship. And maybe, just maybe, I still daydream about wearing her purple strapless gown on a date. 


Kind of. 

Abby: “Picture to Burn” and “Should’ve Said No” also kind of fall into the category of “what elementary school me thought relationships would be like.” Listening to those songs for the first time at seven years old, I thought that breakups would feel like Taylor tearing into her ex’s “stupid old pickup truck” on Picture to Burn, or how on Should’ve Said No, “even now just looking at you feels wrong.” That was how relationships ended in my young, inexperienced mind: fights and fire. Middle school me was secretly a little disappointed when her first relationships just sort of awkwardly went silent — no destroying cars, no passionate hostility.

The longing and jealousy of “Teardrops on My Guitar” was definitely a lot closer to the mark in terms of what breakups have felt like (at least to me), even though it wasn’t even about a breakup. Out of all the songs on this album, I think this and “Our Song” are the ones that kind of hinted at the emotional depths to which this artist would be taking us. 


Abby: This was the album that made me a Taylor fan. I was squished between two of my friends on a one-person chair, and before we descended into the sparkly pink rabbit hole of the games on, my best friend told us we just had to see this music video for her new favorite song.

She pulled up the video for “Love Story” — it was actually the first music video I ever saw. That fresh-faced, high-school, happy-ending version of Romeo and Juliet, both in the song’s lyrics and in the imagery of the video, absolutely captivated me. I was sold. 

I still love those songs, so I was beyond excited for the re-recordings and the addition of songs “from the vault” that Taylor wrote at the time but were left off the original album. I was not disappointed. Listening to those old songs again brought me back to when I first heard and loved them, but it also reminded me how much has changed since then. I’ve lived through some of the experiences these songs are about, the experiences I wanted so desperately to have the first time I heard this album. It brought a whole new meaning to the music I’ve loved forever, and to me, that’s the depth and value of Taylor.

Additionally, we need to talk about “You Belong With Me,” because everything about that song is amazing. The lyrics? Breathtaking. The melody? Fabulous, so effortlessly catchy and easy to sing along to. The girl next door pining for her best friend? Incredible. The music video? FANTASTIC. I live for the mean Taylor vs. nerd Taylor, the notes in the window, the band uniform and cheerleader skirt. Has anything ever been more iconic than nerd Taylor in a beautiful dress showing up at the dance with her “I Love You” note and stealing the boy away from mean Taylor? I think not. 

Andie: In my opinion, Fearless is the album where Taylor solidified her choice to make track five significant on every album. The Debut offered “Cold As You,” which Swift explicitly mentioned was her most lyrically impressive song of the album, and then she hit us with “White Horse.” 

This strategic decision was no minor attack. As an impressionable eight year old who daydreamed of high school romances and still watched Disney movies with a religious dedication, White Horse gave me the narrative I didn’t even know I needed. The song tells the story of a hopeless romantic’s expectations being torn to shreds and faced with reconciliation. Despite the pre-bridge lyrics carrying a melancholic, regretful tone, Swift drives home a classic “know your worth” ending. 

“I’m not your princess, this ain’t a fairytale/ I’m gonna find someone, someday, who might actually treat me well/ This is a big world, that was a small town/ They’re in my rearview mirror disappearing now/ And it’s too late for you and your white horse, to catch me now” 

From early on in her career, Taylor Swift made it clear that she knows how special she is — her expectations of how she should be treated are not skewed; instead, the disrespectful treatment itself is. She describes the importance of standing up for yourself even when it’s hard, a concept especially challenging to execute when applying it to a significant other. This strength and self-assurance isn’t limited to self-application, as Swift wants her listeners to feel the empowerment too. And while it may sound like an exaggeration, the power in this post-bridge chorus is what taught my elementary school self the lesson of accepting nothing less than I deserve. As I sang the ballad out the window, I pictured my teenage years filled with the courage to realize what I am worthy of.

Abby: If we’re talking about breakup ballads off this album, then we obviously have to talk about “The Way I Loved You,” because it hit so hard when it came out and it hits so hard now. There’s always that little part of you that wants back something you had, even though you know it wasn’t perfect, because you just loved it so much.

“and I feel perfectly fine / but I miss screaming and fighting and kissing in the rain / it’s 2 a.m. and I’m cursing your name / I’m so in love that I act insane / and that’s the way I loved you.” 

I also like that the song is up-tempo, because it manages to find that very real place between anger and sadness, which is where that sentiment lives in me: caught between missing it and angry at it. 

We also can’t go any further without talking about “You’re Not Sorry.” To me, this song was vastly underappreciated on the original album, and the re-recorded version really amplifies how good a song it is. I do think the re-recording is better, because Taylor’s grown into her voice more, and because she’s had more of this type of emotional experience. But above all, “You’re Not Sorry” is just a really good song. The sweeping minor keys of the melody, the bitterness of the lyrics — they really bring you back to that stripped-down moment of cold reality. It’s another hint of the emotional depth still to come from Taylor, and indeed the depth she’s showing us here already.

At this point, having spent the last several paragraphs discussing the power and impact of the breakup songs on Fearless, we need to address how strongly Iwe both associate Taylor with breakups. For me, it’s because she manages to capture the emotions so sharply and clearly, and I think there’s something cathartic about listening to those songs when you’re going through those types of emotions. The breakup songs on Fearless are some of the early examples of that.

Andie: It’s interesting, because although Fearless does have numerous breakup ballads on there, it’s always been an album I’ve associated with my childhood perception of romance. Speak Now is when I really start to interweave Swift’s creations with my personal experience. Nonetheless, the album is still extremely significant in its own right.

Abby: The thing about Fearless is that even the songs that aren’t the top ones are still great; the title track is the case in point. That goes for the bonus songs she puts on the platinum version, too — I really like Superstar and The Other Side of the Door. They’re not the best songs ever, but I still really like them. 


Andie: Speak Now is a Taylor Swift album that is criminally underrated. It is a no-skips album with some of her most revolutionary songs, not to mention that it’s sold over 4.7 million copies in the United States to date. It was one of the first albums I grabbed when I started my vinyl collection, with every side of the record as used as the next. Speak Now boasts the inclusion of “Mine,” “Sparks Fly,” “Back to December,” “Dear John,” “Mean,” “Never Grow Up,” “Enchanted,” and “Ours” — it’s clear that very few tracks on this album failed to age as a recognizable exemplar Swift music. Even the songs that don’t fall into that category aged like fine wine for Swift stans. It’s additionally important to recognize that Speak Now serves as somewhat of a transitional album, a precursor to Red with one foot in the world of country and the other flirting with the realm of pop.

The record begins with another one of her country staples, “Mine.” The song details the story of a “careless man’s careful daughter” finding someone she can call her own. It’s a sweet tale of textbook romance and love in niche moments. Similar to “White Horse,” it has a memorable music video illustrating their love story, including a proposal on a boat in a lake. It imprinted into my memory and single handedly created my desire for a meaningful proposal. I’m sure my future fiance will appreciate that one, Taylor. 

Tracks three and four on the album are two songs extremely close to my heart: “Sparks Fly” and “Back To December.” “Sparks Fly” is presumably the lesser known of the two, but played an important role in my middle school career. The idea of, as her chorus puts it, dropping everything in an instant and meeting a lover in the pouring rain felt straight out of a dream for my twelve-year-old self. Better yet, the lyric “get me with those green eyes, baby” felt simply prophetic as I, too, was in a ‘relationship’ with a green-eyed man — a thirteen-year-old boyfriend (hey Kyle) who actually got me into writing in the first place. “The ‘love” I felt for both him and the song felt so true that I decided to name my tumblr handle after the line: (which has since been deleted). How 2014 of me. 

“Back To December” takes me back to the days of Taylor Lautner, where Swift lets the audience in on a moment at the end of the pair’s relationship where she was in the wrong. While seemingly insignificant to the casual listener, this was one of the first times Taylor had a track focused on an apology from her. The lyrics are remorseful yet endearing, offering a grand gesture with a genuine undertone. It’s no surprise this song is still talked about to this day. 

Abby: God, “Sparks Fly” still really gets my inner hopeless romantic. However, word to the wise: if you’re going to go for the big romantic “kiss me on the sidewalk / take away the pain” moment, maybe first make sure there’s not a preschool rope full of toddlers walking by. Also, “Back To December” is so great, but I think it’s important to say that we all broke up with Taylor Lautner when that happened. That relationship was a collective experience and it was absolutely central to my middle school years. I’m pretty sure at one point my friends and I spent an entire afternoon daydreaming about what we thought the wedding would be like, and we all collectively died at their cameos as a besotted high school couple in the seminal 2010 romantic comedy, Valentine’s Day.

I also really love “Speak Now,” the fourth song on the album. It’s an early hint of what we see so much on Folklore and Evermore, where Taylor just creates entire narratives out of one little idea that she hasn’t even experienced. My inner hopeless romantic was literally swooning at the idea of running away with the love of my life after almost losing him to the wrong girl.

Andie: I actually made a music video with my friend to Speak Now that we put on Youtube. With that being said, I think I’m divulging too much information in this article that a wiser woman would choose to withhold. 

“Dear John” takes us on the hurt-filled journey of Taylor’s relationship with John Mayer. At the time of their relationship, she was 19 and he was 32. Lyrically, the song is stunning, filled with intricate descriptions of his misbehavior and compelling characterization of their dynamic. Her writing abilities really shine through, and while the majority of the song is spent describing the relationship’s toxicity, the standard “know your worth” bridge elicits major success yet again. 

“You are an expert at sorry, And keeping the lines blurry/ Never impressed by me acing your tests/ 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.”

Little is as therapeutic as screaming those lines with their beautiful prose and unquestionable power. As a quick aside, I recently learned from The Ringer’s “Every Single Album: Taylor Swift” podcast (upon Abby’s recommendation) that the guitar riffs in “Dear John” mirror that of John Mayer’s “Gravity” as a satirical diss. The woman is such a genius — I would give anything to tour the inside of her brain. 

Abby: “White Horse” was certainly the moment Taylor decided to rip us apart every track five, but good GOD does she go in hard on Speak Now’s track five with “Dear John.” Has anyone ever been so comprehensively torn to shreds before or since? And damn it, she’s right. SHE WAS TOO YOUNG, JOHN.

Andie: To my prior point, “White Horse” as a track five only served to solidify the pattern, but “Dear John” … this song brought it to the next level. It’s almost as if she gave us “White Horse” as an ease into “Dear John,” and “Dear John” as a much more emotionally jarring ease into “All Too Well” — but more on that later. 

“Dear John” leads us into “Mean,” a song that while I personally no longer opt to listen to on a casual Tuesday due to its overly country overtones, has a backstory that makes it remarkable. After famous music critic Bob Lefsetz accused her of using autotune, Ms. Swift struck back with this lovable clapback of a song that won over spectators of the beef. 

With tracks one through six being essentially deemed as untouchable Taylor classics, songs that follow like “Never Grow Up” and “Long Live” evoke a different kind of feeling, one arguably just as memorable: youthful innocence. To this day, listening to “Never Grow Up,” a song that intricately details the life of a woman from childhood to adulthood, makes me sentimental. The growth of emotions with this song makes sense — it’s a song about growing up that I first listened to when I was 12 and am still including on playlists as a 21-year-old.  In my early years of listening, I would long for my future life as a young and free adult, empathizing with the lyric’s articulated teenage angst (“At 14, there’s just so much you can’t do and you can’t wait to move out one day and call your own shots”). Now, I relate to the bittersweet bridge with a nostalgia that feels almost unsettling.

“Take pictures in your mind of your childhood room/Memorize what it sounded like when your dad gets home/ Remember the footsteps, remember the words said/ And all your little brother’s favorite songs/ I just realized everything I have is someday gonna be gone.” 

The way she describes aging in this scene evokes a sense of sadness and understanding that a person may be quick to diminish until they understand it themselves. One of the only indisputable truths in life is that we age — nothing can stop us and everyone around us from aging. Life stops for nobody. The years that many people spend during adolescence wishing for the future should be spent taking in the joys of growing up; things change too quickly for us to not. As a rising senior in college writing this from my childhood bedroom, spending many weekends with my family or high school friends for what is most likely my last summer in my hometown, I understand this idea more than ever before. And with this in mind, it feels a bit crazy to me that one song captured both the accurate perspectives and emotions that came with each of my life thus far, aging with me as I came into my own. 

My favorite song of the entire record is “Last Kiss.’ Now, this take may come with some bias because it was my first real break-up song, but I would argue it is the most lyrically impressive of the album. The song captures Taylor’s experienced intimacy in a personal, yet still relatable way. By including mentions of specific details — the image of a clock at 1:58AM, the specific date of July 9th — the listener is brought along a montage of her relationship’s closest moments. She never mentions a name (it’s actually quite difficult to pin down who it’s about)), yet the listener can feel her hurt. It’s writing that not only feels real, but close, regardless of literal proximity or familiarity. The bridge emits this feeling to the nth degree: 

“So I’ll watch your life in pictures like I used to watch you sleep/ And I feel you forget me like I used to feel you breathe/ And I’ll keep up with our old friends just to ask them how you are/ Hope it’s nice where you are.”

It’s believable heart break: you hear it in her voice, you feel it in her lyrics. With this in mind, it makes sense that it was my first break-up song. At a raw fifteen years old, I believed I was in love with my first real boyfriend. We lasted an impressive six months, only for him to end it with me over the phone. But with the guidance of “Last Kiss,” I had an anthem for my introduction to the gut-wrenching hurt associated with relationships’ conclusions. And so I sat on my bedroom floor wearing his soccer warm-up jacket, as the chorus so effortlessly instructed me to  (“I’ll go, sit on the floor wearing your clothes”), screaming the lyrics until I found the strength to get up. And just like that, with the help of Taylor Swift, I slowly but surely moved on from my first heartbreak. 

Abby: I think “Enchanted” is probably my favorite song off Speak Now. The song just captures so perfectly that feeling of oh my god I think I just met someone was that a thing, of texting your friends in all caps about a boy.

This night is sparkling, don’t you let it go/ I’m wonderstruck, dancing round all alone/ I’ll spend forever, wondering if you knew/ I was enchanted to meet you…

The ephemeral shimmer of the lyrics, the hints at something that could shimmer and spark and break into something new — it’s so perfect. I love the imagery, whimsical and fantastical as it may be, because damn it, sometimes meeting someone does feel magical, sort of slightly unreal, and it’s such a perfect depiction of those moments. Also, the fact that she wrote this about the guy from Owl City after meeting him once is truly a testament to her talent and ability to make something so beautiful from such a small moment. It’s the sort of imagination that becomes trademark Taylor.

Andie: I want to just mention the guy from Owl City’s response to the song: a well-intentioned yet poorly executed rendition of the song coupled with a cringey note. Let it be known

The moral of the story is that there is absolutely no reason to sleep on Speak Now. I’d go as far to say it’s the unsung hero of her collective discography. Between the two of us, we could have written an article about every song individually. They’re all full of that much depth, and simultaneously worthy of that much analysis. It’s a prime example of Taylor Swift’s undeniable talent — one that carried into all of her albums, regardless of genre, to come.

Statement Managing Editor Andie Horowitz and contributor Abby Snyder can be reached at and