A Beginner’s Guide to Taylor Swift

Posted: by The Editor

Art by Miranda Reinert

Taylor Swift is punk as fuck. 

Rather than give a drawn-out introduction to Taylor Swift’s history, I’m going to recognize that you probably already have a preconceived notion about her, and that’s cool. Let’s skip the bullshit and get this out of the way: If you hate Taylor Swift because she makes music about her exes, you have internalized misogyny. Everyone makes music about their exes, even your favorite musicians. Call a spade a spade.

But if you want to dive into different music, music that broke records, made millions and helped define what it means to be a singer/songwriter, that’s what this is for. No one is going to judge you for reading this guide, and I promise it won’t go against your punk identity. I am going to give you the highlights of Taylor Swift’s career so far. 

(Also – fuck record labels that don’t give their artists ownership of their music!!!!) 

Taylor Swift (2006)

Great if you like: Country, angry breakup anthems, songs with four chords

This is where it all began, right?

I’m going to be straight up: I don’t like this album that much. That’s mostly because I’m not the biggest fan of country. However, there’s songs on this record that embody what it’s like to be a teen and how angry you can get if someone breaks your heart. 

For instance, “Should’ve Said No” has a beautiful violin/acoustic guitar thing going on as our girl croons about some cheating fuckboy. In combination to all that, this pulsing drum beat and electric guitar pair up with the violin in a power-country way I really love. Great song. 

If slow ballads are your thing, consider “Mary’s Song (Oh My My My).” It’s one of the most country songs I’ve ever heard and shows how good of storyteller Taylor has been since the jump. The production isn’t doing much, just some guitar twangs and full band magic. But, if ballads aren’t your thing and you’re just trying to jam out, boy do I have a song with you.

“I’m Only Me When I’m With You” is proof that Tay writes the hell out of songs about friends, just listen to it if you don’t believe me. One of my favorite songs of hers, the track’s energetic, simple, and fun. It makes me want to go to a hoedown and dance around with my two best friends. “When I’m with anybody else, it’s so hard to be myself,” is a huge lyrical mood, and them being above some strings and harmonica makes it all the more enjoyable. 

If you listen to S/T, you’ll probably be surprised that how young she sounds. I think the Taylor Swift voice that most are used to hearing didn’t kick in until her sophomore record, but if you like fun country music, Taylor Swift is cute and a good time!!

Fearless: The Platinum Edition (2008)

Great if you like: Country pop, slow songs, chill pop

To me, Fearless is not her shining moment. But the great thing about Fearless is its versatility—Tay is a super thematic artist, but Fearless and Red are expansive with experimentation. And for Taylor being only 18 at the time, the songwriting is remarkably mature. She recognizes what she is and isn’t with this record and puts it on blast. For that, I love the journey of Fearless, I love the message, and I appreciate how it took over the industry.

To begin, I want to point you to three incredible songs that embody the concept of the record, “Jump Then Fall,” “Untouchable,” “Forever & Always (Piano Version).” I think of these songs as one and the same. They are calm and beautifully executed with minimal synth, strings, and piano. If you are skeptical about Taylor’s ability to make simple, passionate music, just give these a listen. You’ll get twinkling guitar solos and fun little vocal ad-libs, something I love that she does (the “Hoh!” in “Jump Then Fall”).

If you can’t get enough of the #vibes on this record, I’ll give you one of my favorites, the title track. When it comes to “Fearless,” I didn’t like this song until I saw a live video. She gives a little speech in it that’s absolutely beautiful. The slow “Yeah,” she sings before those gorgeous electric guitars come in makes me think of igniting some sort of engine before the song gets under way, a progression that is very romantic.

But if you don’t want to fall in love and you want a banger, “Forever & Always” has your back. I’ll go to bat for its technical build. I imagine Taylor writing it in like, 11 minutes after Joe Jonas dumped her in a 27 second phone call. It’s wild, emotional, hardly makes sense lyrically, and that’s why I love it. If you’re getting over a breakup, every word makes perfect sense. If you can appreciate a solid electric guitar solo, mid-tempo drums, and random harmonies, trust me, this is for you.

The most fearless kind of love is self-love, and that’s the biggest takeaway I have from this record. It made me feel like being crazy is okay, because it is. And sometimes, you just need to jump on your bed and scream the lyrics to “You Belong With Me” to get through a rough time.

Speak Now (2010)

Great if you like: Fairytales, pop music that claims it’s country, ballads

I LOVE Speak Now. Storytelling. Emotion. Fireworks! Speak Now has Taylor’s longest, most whimsical songs. Not only that, but fun tunes that are so dramatic, like “Mine.” But I want to focus on others like “Enchanted,” which made a Rolling Stone music writer nearly cry. It made Owl City record a cover in which he proclaimed his love to her and release it, with a love letter, on Valentine’s Day. 

It also makes me think about little beautiful moments in life, like how songs like “Enchanted” build into something spectacular. Beginning with just a single guitar up until the first chorus, the full band kicks in and keeps the same tempo going into the second verse, where her falsetto builds upon that. And the bridge, oh my God, it’s like the song spins you around with the way the guitars swirl with her voice. The second bridge, “Please don’t be in love with someone else,” is my favorite part of the entire song. It strips itself down to the beginning, and while it repeats and builds, the rest of the instruments fills itself in until she wails (in tune!) before the last chorus. While this is a beautiful (happy!) ballad, let’s say you’re looking for something to mend a broken heart. “Dear John” is here for you. 

John Mayer doesn’t deserve this song written about him. This is what it’s like to get dumped and look back only to realize you had rose-colored glasses on the whole time. One of her most beautiful bridges comes from “Dear John.” Watch her tour performance of it, there’s nothing more empowering than seeing fireworks go off right at the climax. If you can hold that note in one breath, you deserve an award, because it took me months.

But to unleash your crazy side and not having time for six minute songs, enter “Haunted.” Who hurt her like this? I don’t know what’s happening instrumentally, but it makes me feel like I’m running through the woods from, I don’t know, werewolves or something. Maybe it’s the loud bells ringing throughout. Here, Taylor makes wild choices vocally and musically and I love that journey for her.

Stand up for yourself, let it out, live in your daydream, do whatever, as long as you’re shamelessly being yourself. That’s what’s important, that what Speak Now encompasses.

Red (2012)

Great if you like: Slow heartbreak delicate pop, metaphors, guitars and drums, deep cuts

Red was underappreciated when it first came out and I never understood why. People say it’s not sonically cohesive, but it flows so beautifully, from one song to the next, and has underrated hits “Red” and Treacherous,” which I HIGHLY recommend. Honestly, listen to the whole record, but we’re here for the standouts, starting with “State of Grace,” which is without a doubt her best album opener. “State of Grace” is so special and I don’t think she’ll make another song like it again. 

The message, of not expecting a person to enter your life but feeling anew and understood because they have is handled so well on the song. Sometimes you just know that someone will never leave you the same. Which brings me to “All Too Well.” Every Taylor fan has their own feelings attached to “All Too Well” and since just explaining the song wouldn’t quite capture it, here are mine:

Crazy how the meaning of this song has changed for me with every year I grow older. I’ve gone through two friend breakups in the latter half of 2019. Both hurt and are still vivid in my mind. It doesn’t matter if you spend 11 years or 3 months with a person, because when you know them inside out, you remember everything. For me, it doesn’t start until 2:56, where the second half of the song presents itself as something entirely new. It picks up in pace and paints a more emotive picture than the depressing first half. I don’t know what it is about “All Too Well,” other than that this song was once a part of Taylor’s life, and now, it’s a part of the world, but it touches fans. A little heavy for what you’re feeling? Here’s a palette cleanser for you: “Starlight.” 

It’s just a really good pop song. It has everything: a fun love story told to Taylor by Ethel Kennedy (remember that summer she dated a Kennedy?) and I hold it in the same regard as “Holy Ground,” another jam. It has a story of its own within Red, and I love that. A perfect reminder to dream. 

Red evokes something in everyone. Not every song will do it for you, but the ones that do stick with you. For me, that’s “State of Grace,” “Treacherous,” and “The Lucky One.” It’s synonymous with fall and magical with feeling, a near perfect and forever eternal album. 

1989 (2014)

Great if you like: Jack Antonoff, Duran Duran, pop covered in pop, dancing

Whew, 1989. This was announced as Taylor’s big breakaway from country, a transition that actually happened with Speak Now. She switched to pop, hard. 1989 isn’t her deepest, but it doesn’t need to be, it’s fun. Consider “Style,” a song my best friend loves. The electric guitar in the beginning is sexy. While the rest isn’t, it’s dance-y, and there’s nothing like driving with your best friend with the windows down screaming, “Take me home!” in the summer. You know what else is good for that?

“New Romantics” is only on the deluxe version, which is dumb, because it’s one of her best. Our good sis realized we go up for DLX 1989, because it eventually became a single. Not only is it about enjoying friends, but yourself. So what if people put you down and you get a little immature? The best people in life are free, of emotional distress, anger, and insecurity. 

I want to mention a song that deserves more recognition and sometimes gets lost in the throws of “I Wish You Would” and “Out of the Woods.” 

“I Know Places” is not only a bop, but it’s one of the more sonically interesting songs she’s made. With 1989, T does weird little things, like put her actual heartbeat at the beginning of “Wildest Dreams,” that kinda makes sense. In this one, she gets really into the theme. Tay believes in “I Know Places.” Before the second chorus, she screeches the last couple of words before the bombastic fanfare of the chorus floods in with its pulsing tempo and I’m obsessed with it. That makes the entire song for me. 

1989 shouldn’t be disregarded as quickly as it is. Taylor moved to New York, found magic, and took a nosedive into how it felt. It’s cute, it’s compact, and it gets the job done. And I have to mention “Clean,” because although it gives me anxiety, a fan gave an excellent point about how it can be refreshing and wash you into being a new person. 

It slows the record, points out the bad parts about getting over someone, but all of the wonderful effects tied with it. And that’s how 1989 ends. It’s a party of a journey, covering up heartbreak and confusion with a dance. 

Reputation (2017)

Great if you like: Black sheep records, hidden gems, dubstep

This record…is not my cup of tea. Which is why I enlisted the help of Tay fans to give retrospective about why they love it, but I do want to point to one song I love, “Call It What You Want.” It’s a slowed down love song that’s chill, calm, and perfect for easy listening. 

The reason I don’t like Reputation is largely because there are production moments or songs that are almost there but don’t feel complete. To put it a different way, I know what Taylor can do and this record isn’t the best show of it. However:

It’s the precursor to the stylistic choices she made with her next album, and the harmonies fit the synth like a glove. And that brings me to “Delicate,” a song fans strongly implored I listen to. Admittedly, it bangs. 

Synth is her partner while building the chorus, which feels like a dark dancefloor. She makes the sound in each section of the song completely different. Plus, the lyric “My reputation’s never been worse, so you must like me for me,” is a good one to point to just in general. 

Interestingly enough, “I Did Something Bad” plays like a K-pop song. It survived half-baked synth and production and feels like an entire, finished work. And it’s so fun! Lyrics, dance breaks, everything is thematic and it’s easy to point out that this is Taylor’s comfort level.

“New Year’s Day” is a slow tune that is this record’s ode to friendship. Songs exist about the party, but few effectively capture the aftermath, and who will be with you cleaning up the spills and throwing away streamers. That’s what this song does. Lyrically, it’s a cute exploration of a realm of friendship Taylor is maturing into, giving vivid examples of what it’s like having friends when you get older and wiser. 

There are good things about Reputation, like its ode to themes. Technically, it’s ambitious and timely; 2017 was a year for dark, sexy, weird pop music. I like that “America’s Sweetheart” wanted to dabble in that as a stark break from her previous track record.

It keeps the vibe of “I’m edgy, here is my dance club album because I’m a mess and that’s okay” pretty much consistent. It’s like if 1989 took away the birds and the glitter and replaced it with three shots of tequila and a cheetah print skirt. 

Lover (2019)

Great if you like: Therapeutic pop, killer lyrics, emotional blows

There’s so much to say about Lover. It takes the best parts of previous records and escalates them in a package of maturity and clarity. 1989 and Reputation were dubstep-forward (and so is “I Knew You Were Trouble,” a fucking banger). Lover takes those ideas and molds it into an outfit of elegant, gentle mixing. Instead of drowning in electronica, “I Forgot That You Existed” folds it with piano. TBH, I forgot Calvin Harris existed too.

 “Miss Americana & The Heartbreak Prince” is one of many beautiful, reflective moments on the album. It goes back Fearless, but how now, high school sweethearts are a distant daydream and the time to wake up is now, because our country is a mess. It could be underrated and shouldn’t; remixing the classic high school chant “Go! Fight! Win!” into a war cry. Other gorgeous song, “Cornelia Street,” strikes a perfect chord in-between nostalgia and heartbreak.

But now, I get to talk about my favorite song she’s done, “Cruel Summer.” If you want to lose your mind in a pop way, here it is. I love the production, synth, drums, and harmonies my Alto 2 voice clamors for. The lyrics — vulnerable, and as such, relatable. As a broke black woman, there’s not much I can relate to with Taylor, but I feel her on “Cruel Summer,” in which she admits to sobbing drunkenly in the back of a car due to a betrayed heart. 

“I love you, ain’t that the worst thing you ever heard? (He looks up grinning like a devil)” hits, especially as the rest of the song stops. And Tay was feeling it too—she’s screaming at this point, whereas the rest flows like a vibe.

Though Lover is very emotionally mature, there are still songs that aren’t, and that’s fine for smooth listening. “Paper Rings,“I Think He Knows,” and “London Boy” are cute, fun, repetitive, and an ode to her boyfriend. They do want they need to.

Lover is a resolution to the past, an indulgence in the present, and a confident, stable, solemn look to the future in a technically mature pop way. I wouldn’t be surprised if Taylor took a break from music following this album. From “False God,” to “The Man,” “Daylight,” and “Afterglow,” she’s said everything she’s been wanting and needing to. Away from drama, daydreams. Every song captures closure. Lover just might be her masterpiece, so I’ll close with the spoken mantra she closes the record with:

“I wanna be defined by the things that I love. Not the things I hate, not the things I’m afraid of. I’m afraid of the things that haunt me in the middle of the night. I just think that…you are what you love.”

And Movie Songs (Her Best Work)

This short section is to mention that if you want each era of Taylor to be spelled out in a couple of songs, look at the work she’s done for movies. Every song is a win, every song is so great. I love them. I might miss one or two, but this is a guide of highlights. 

  1. “Crazier” – Hannah Montana: The Movie (2009)

A slow, sweet jam about falling in love. If Britney Spears took “Crazy,” slowed it down, and made it country, this would be it. She carries her vocals in a way you don’t really see after Fearless, and I love how they intertwine with the story and makes them feel alive.

  1. “Today Was A Fairytale” – Valentine’s Day (2010)

This has Speak Now written all over it. Just look at the title. This is like a compact version of “Enchanted” with less bells and whistles; it’s super cute. I love the vocal control she’s serving as well. 

3 & 4. “Safe & Sound” and “Eyes Open” – The Hunger Games, (2012)

These are so beautiful. Truly two of my favorite songs from her. “Safe & Sound” is so hauntingly AMAZING. I wish she had more songs like this, where she vocalizes with incredible control and expertise. “Eyes Open” uses those drums she found a home in with Red and it works so well. I just..I love these songs. 

  1. “I Don’t Wanna Live Forever” – 50 Shades Darker, (2017)

Anyone who was my sorority sister when this came out knows I lived and breathed this song. It’s so hot. That’s just it. Tay sounds great, Zayn sounds great, their obsession with synth sounds great, and I’m here for ALL. OF. IT. STILL. 

If you’ve stayed with me for this long, I’m really glad you have. Thank you. Happy listening and SCOTT GIVE TAYLOR HER MASTERS. 



Kayla Carmichael // @kaylacarmicheal 

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