Last fall, Taylor Swift’s re-release of “Red” rekindled the discussion about unapologetic femininity. That controversy around her re-recording of masters and the conversation about being allowed to love her work, made me listen to her entire discography in order of release. I was aware of her work and her profile only as someone who pays attention to trends and media, not as a fan.

I love songwriting so much because there’s an element to it that is still really mysterious—like I think any songwriter will tell you, when you get an idea you’re not quite sure where it floated down from, but if you can grab onto that idea and turn it into something, a piece of music, that’s where craftsmanship comes in; that’s where you have the opportunity to learn and to nurture that craft. — Swift on the art of songwriting, Variety

I quickly realized her technique is hugely diaristic. In a 2011 interview with The New Yorker, Swift identified primarily as a songwriter: “I write songs, and my voice is just a way to get those lyrics across.” You see this emphasized in each album, even early in her career.

Yet, she has been dismissed as that girl singing about breakups. This made me wonder if her work was being dismissed as shallow in the same way that most women’s artistic pursuits are overlooked and under-appreciated.

Listening Through Her Albums

My editing and search engine optimization services create extended windows of time for listening. I listened to all of these songs over two working days. (And now Spotify thinks I’m a certified Swiftie.)

In general, criticizing Swift’s discography feels like picking on an earnest drama nerd. I appreciate her effort.

Taylor Swift Album

I’ve been to enough weddings that I’m not ignorant to the songs from this album. Somehow, I didn’t know that Tim McGraw, Teardrops on My Guitar and I’m Only Me When I’m With You were Taylor Swift songs. The Outside  and Tied Together With a Smile would have appealed to me if I had heard them at the time of release. Mary’s Song and Our Song are the tunes I most associate with this Swift era — marketable ballads that saturated the charts. 

“She’s got everything that I’ve got to live without…” in Teardrops on My Guitar provoked me to look up biography details — demolishing the authenticity of that statement. Her childhood in Pennsylvania, education at a Montessori school, private music and lessons in New York, and a parent willing to homeschool her and frequently drive her to Nashville, relays a level of privilege contrasting the persona this album is built around. 

Her stories resonate most when they are grounded in stories of what she likely actually experienced, like falling too deeply in love with jerky teen boys like in Should’ve Said No. Who hasn’t thought, “Was it worth it? Was she worth this?”

Swift adores her blue jeans and pretty dresses — like all of us who inexplicably layered them together in 2006. From the start, apparel plays a role in her lyrics and add context to her relationships. Jeans become a proxy for authenticity while dresses signal romantic inclinations. Tim McGraw notes both faded blue jeans and a little black dress. A Place in this World also mentions old blue jeans

“I hate that stupid old pickup truck you never let me drive” from Picture to Burn illustrates how Swift doesn’t shy away from cliches if they are a precise fit for her meaning. This is actually difficult to master in writing. Cliches work best when they are a shorthand for universal thoughts and feelings. But, they spoil good writing when you use them as a crutch. When she places them within highly specific and personal ballads, it roots her story with something known and familiar. 

Appropriate for her age at the time, this album sounds youthful with statements like, “I don’t know what I want so don’t ask me,” in A Place in this World. Similarly, Stay Beautiful, Mary’s Song, Invisible, and I’m Only Me When I’m With You capture coming-of-age moments with tenderness and hope. 

Fearless Album

When you listen to this album you must remember how sharply divided country and pop were prior to Taylor Swift’s climb. Billy Ray Cyrus never successfully brought together his pop and country personas, getting backlash from both sides after Achy Breaky Heart. Concepts like Lady Gaga dropping a successful country album probably wouldn’t have made it past the pitch. And Lil Nas X was just a mind-blowing glimmer in his fans’ eyes. 

This is the album where Kanye West interrupted her award speech — which some say launched her to that next level of stardom. That seems like the cheapest way to explain her talent-driven trajectory. 

Speak Now Album

This album echoed themes of love, heartbreak, and insecurities — from an adolescent perspective. Songs like Back to December and Dear John cemented her high-profile dating relationships while overshadowing her talent. I recall the media criticizing her behavior — egging on misogynist attacks. 

By this time, Swift had crossed over from country music to the mainstream pop market. As her profile rose, her words remained vulnerable and diaristic. Her artistic method opened her to attacks from talking heads — while forging a deeper connection with her fans.

Red Album

Swift delved into the tumult of toxic relationships and ending romance on Red. The title track maps the fading tones of a relationship with colors — “losing him” is blue, “missing him” is dark gray, and “loving him” is red. The rest of the songs on the album are thematically tied together in their appreciation of the beauty of looking back after loss. 

1989 Album

If Red is a breakup album, 1989 is a story about moving on. Songs like Blank Space, Shake it Off and Clean look to the future while acknowledging difficult times. 

From a business perspective, Swift flexed her power during this album’s release. She pointed out the importance of albums to artists and fans. Then, she removed her entire catalog from Spotify. Swift argued that the streaming company’s ad-supported, free service undermined the premium service, which provides higher royalties for songwriters. Then, in an open letter, Swift criticized Apple Music for not offering royalties to artists during the streaming service’s free three-month trial period and stated that she would pull 1989 from the catalog.

In response, Apple agreed pay artists during the free trial period. Eventually, she re-added her entire catalog plus 1989 to Spotify, Amazon Music and Google Play and other digital streaming platforms.

Also during this time, Swift’s intellectual property rights management and holding company filed for 73 trademarks related to Swift and the 1989 era memes. Each of these actions made the general public more aware of music rights and how the music industry operated.

Reputation Album

Reputation was inspired by Swift’s celebrity, her relationship with the press — and poses the strongest cultural commentary. This is when I really began to pay attention to Swift as an influencer — with reach beyond the music industry. She wasn’t simply releasing music, promoting merchandise, and trying to stay ahead of the gossip rags. Swift was starting bold conversations.

When Kanye West released Famous, he posed with life-like, nude sculptures of several celebrities — including Swift. He also rapped, “I made that bitch famous” referring to his earlier interruption of her award speech. When Swift criticized the lyric, Kanye and then-wife Kim Kardashian, released a heavily-edited video on social media — implying Swift approved the lyric. Their public spat continued on twitter with emojis of snakes referring to Swift. 

Katy Perry drug Swift on social media over a mix-up with backup dancers, which added to Swift’s personal controversies in the spotlight.

Around that same time, she won her lawsuit against radio DJ David Mueller — who had sexually assaulted her. Mueller attempted to sue her after he was fired because of his actions. That trial preceded the official #MeToo movement, signaling the forthcoming reckoning. 

In turn, Swift used that incident, feuds with other celebrities, and the public’s abuse, to promote Reputation’s album. It was a hard turn, stylistically and lyrically, for her as an artist. Songs like Look What You Made Me Do and This is Why We Can’t Have Nice Things feel like they’re written by a pop alter-ego. It’s Taylor but, she’s angry and sort of done with everyone, as she explains saying,”I’m sorry, the old Taylor can’t come to the phone right now “Why? Oh, ’cause she’s dead!”

In songs like Delicate, Swift’s lyrics-as-a-diary method shine brightest. She reminds the listener that she’s a human with feelings and a family.

Lover Album

Swift promoted Lover as her realization of the “full spectrum of love”. This spans romantic love to female friendship to allyship with marginalized communities. It’s a fun album with a less serious outlook that the previous album. At the same time, she owns the pop-music machine — spinning singles into hits. The Man, You Need to Calm Down and Me! illustrate Swifts awareness that social media would break her ideas down into snippets.

During promotion for Lover in 2019, Swift became embroiled in a publicized dispute with talent manager Scooter Braun and her former label Big Machine. Although Swift had been trying to aquire her masters for years, Braun only allowed her to do so if she exchanged a new album for each older one.

Declining that offer, Swift announced that she would re-record her tracks.

Folklore and Evermore Albums

Although Swift doesn’t refer to the twin albums Folklore and Evermore as pandemic projects, they did come out with little formal promotion. This is the album where I discovered Taylor Swift — meaning that my head turned out the sound and lyrics. I wanted to know what this artist was all about and listen to every song on her record.

Like her body of work, the songs contain cute phrases that drop nicely into social media captions. In Folklore, most of the songs feature her return to fictional narration and diary-entry lyrics. Even if the “characters” and story arcs are not from her life, you can hear Swift’s experiences in each song.

Evermore appreciates pretty things and this record sounds like a lace tablecloth atop a piano. This album dropped close to Folklore and I heard them around the same time. Easy listens include willow which hums “…I’ll come back stronger than a nineties trend”

Separating her ballads from her love songs is difficult with songs like champagne problems, happiness, coney island, ivy, long story short, and no body, no crime. As a final reminder, the Venn Diagram for a Taylor Swift love song and a Taylor Swift breakup song is a circle.

My monogamous relationship feels like this — I envision how the story could end as the bloom falls off the rose. Loving deeply, for storytellers, means experiencing the scope of your life with someone all at once. You see the beginning and end, in parallel, as you’re living in the middle of it.

Songs such as dorothea, cowboy like me, majorie, and right where you left me, are still highly relational with touching lyrics such as, “If I didn’t know better, I would think you’re singing to me now.”

Clothing still plays an active role in her lyrics. Happiness mentions the dress she wore at midnight. Written and recorded throughout the pandemic, these settings are deeply domestic with mentions of nice silverware, special art supplies — making them especially relatable to a public trapped inside.

Red (Taylor’s Version) Album

Then, my Instagram feed swarmed with women saying, “You know what, I’m allowed to like Taylor Swift.” The release of Red (Taylor’s Version) was a calculated power-play against her previous business partners and the music industry in general. But, it was also an artistic albatross. 

The songs were longer, adding in the original lyrics. This makes each song feel more authentic and somehow, precious.

Final Thoughts

As I went on this two-day discography journey, it reminded me that we are allowed to like what we like. Sometimes, I question my own creativity — asking if what I made was original or good enough. If it’s twee, tawdry, or trite, who’s to say?


Also, did I miss it or does Taylor still need to write a song about her cats?