In honor of her new album being released last week, eleven of my favorite Taylor Swift songs — not in order — and occasions for listening to each.
My favorites change often, so consider this a tentative, pre-Midnights list (though Mastermind and Midnight Rain have been looping as I edit supplementals, possible album review coming your way at some point?).
- All Too Well
It wouldn’t be a Taylor Swift list without this fan favorite. It truly is some of the best of her songwriting, not just in the specificity of certain details — the iconic red scarf, the hazy glow of a refrigerator light — but also in how carefully it freezes and examines a memory. “So casually cruel in the name of being honest” and “’Cause there we are again on that little town street / You almost ran the red ’cause you were lookin’ over at me” are some of my favorite lyrics of hers.
Listen while: looking through old photo albums, passing through a small town in the fall, saying goodbye to someone or something.
- State of Grace
A deep cut! Red was one of the albums that soundtracked my elementary school years, but I rediscovered this track more recently. It has such an expansive, rich sound, and the driving drums and guitar add to the immediacy of the emotion it manages to capture. It’s ultimately a love song, one filled with possibility and the feeling of a perfect moment in time. I love the phrasing of a “state of grace.”
Listen while: exploring a new city, watching the leaves transform.
- Style
Pop perfection. 1989 reigns supreme in my personal ranking of Taylor’s albums, and Style is just such a great song. It’s so atmospheric and lush, and this is THE song to scream in the car, especially when the chorus hits. The build up to the bridge is exultant, and the “James Dean daydream” part is so fun.
Listen while: driving late at night with friends, daydreaming.
- Cardigan
A gorgeous, immersive track, Cardigan weaves a bittersweet narrative with dreamy production. Honestly, I don’t love the chorus, but the verses are fantastic, filled with enough metaphor and vivid imagery to convey a movie’s worth of emotion.
Listen while: reading a heartbreaker of a book, going on a walk alone.
- Fearless
It’s just so good! An unapologetic tribute to being young. You can’t help but get caught up in the giddy joy and vivid imagery of falling in love for the first time, and the playful, heartfelt turns of phrase she slips in, from “head first fearless” to the detail of a “glow off the pavement” after it rains. I love the line “I don’t know how it gets better than this,” and how genuinely exultant it feels.
Listen while: coming home from a football game, going outside during a summer rain.
- Tis the Damn Season
Such an underappreciated track, and perfect as the holiday season approaches. It’s sweet and quietly heartbreaking, with a twinge of bittersweetness as she promises her lover they can “call it even.” I really enjoy the rhythm of the lyrics, how they almost fall into one another: “Sleep in half the day just for old times’ sake / I won’t ask you to wait if you don’t ask me to stay” is a personal favorite. Also: Robert Frost reference.
Listen while: feeling nostalgic during the holidays, contemplating what a hometown means when you leave.
- Cruel Summer
A dreamy, catchy track that conveys perfectly an intense, head-over-heels balance of ecstasy and heartbreak. There’s a gorgeous build up to a bridge that is pure catharsis, with Taylor’s isolated voice screaming, “I love you, ain’t that the worst thing you ever heard?” There’s a warmth and an intimacy to the details, from angels and devils to a garden-gate rendezvous, that mark this as a fantastic summer anthem.
Listen while: Pulling an all-nighter to watch the sunrise, drinking ice water on a hot summer day.
- Mine
A classic Taylor track, and for good reason. The lines “You made a rebel of a careless man’s careful daughter / You are the best thing that’s ever been mine” are a triumph, and speak to her ability to inhabit a character. The song is a swirl of bubbly energy, with a compelling simple honesty to the lyrics as she tells a love story.
Listen while: people-watching while sitting at a café, writing someone a snail-mail letter.
- New Romantics
A bonus song from 1989 that exudes carefree, big-city euphoria, New Romantics is anthemic. Taylor starts off the song with a detached, almost mocking reflection on young adult ennui, but by the time she declares that “we’re the new romantics” and calls heartbreak the “national anthem,” her voice soars, calling for a surrender to the freedom of feeling.
Listen while: gossiping with friends, looking down at the streets of a city from a high-up window.
- Cornelia Street
An almost reverent track dedicated to the painful nostalgia of associating a physical location with a person or memory. The vulnerable exploration of uncertainty against delicate piano and synth coupled with intricate details form a compelling narrative.
Listen while: picking up painting for the first time in a long time, going outside for fresh air in the winter.
- Tim McGraw
I’ll be honest: this is the only song on her debut album I have more than a passing familiarity with, but I’ve come to love this one. Would 110% recommend checking out Maggie Rogers’ cover. Listening, one can suddenly picture how she rose so quickly to Nashville fame: at 15, Taylor seems to have already proved herself able to conjure clever verses — “He said the way my blue eyes shined / Put those Georgia stars to shame that night / I said, ‘That’s a lie’” — and heartfelt choruses, praying that an ex remembers her when she sings “But when you think Tim McGraw / I hope you think my favorite song.”
Listen while: stargazing, spending time with an old friend, replaying old conversations.
That’s the 11! Let me know your favorite Taylor songs, or thoughts on Midnights if you’ve listened.
My God Ivy,
This blog might have been lauding Taylor’s songwriting, but your commentary on each song is just as artistic. I’m shook.
First of all, the attention to detail for each listening situation does not go unappreciated. “people-watching while sitting at a café” is such a vibe, and “reading a heartbreaker of a book” sounds difficult to do while listening to music but I’m so into it. “Looking down at the streets of a city from a high-up window” conveys such a beautiful image; 50% the lofi girl and 50% what I imagine my apartment will be like in 10 years. So stunning ivesters.
Beyond that, there are just so many little tidbits here that need unpacking: “conjure clever verses” is first on my list. The consonance of the c, the repetition of the syllable “ver” which also slant rhymes with “jure”, and even just the rhythm of 3 words with 2 syllables makes it oh so poetic. It’s just pretty Ivy.
I’m also so glad that you started with All Too Well. The 10-minute version is full of so many lyrics that deserve recognition; the “casually cruel” line cuts so deep into my heart, but you definitely picked the best two with that one and the “almost ran the red”. I haven’t listened enough to the point where I can sing the whole thing, but you better believe I’ll be belting it the next time we drive home on a Tuesday afternoon.
Hey Ivy! I also love Taylor Swift so I enjoyed reading your post. I think you chose really good songs to write about (but then again, she doesn’t really have any bad ones). The lyrics you chose were all thought-provoking. I liked how you gave situations for each song; I found them to be really accurate. Style definitely is pop perfection, Cardigan is perfect for any heartbreaking novel, and Fearless represents youth, specifically high school. Red was also the soundtrack to my elementary school years (along with Speak Now). Some of her songs that I think are underrated are The Last Time/Red (Red), You’re Not Sorry (Fearless), Seven (Folklore), and Coney Island/Gold Rush (Evermore (honestly, this entire album)). I also strongly stand by the fact that “Epiphany” from Folklore is such a good song both lyrically and melodically and doesn’t deserve the low standings it gets on social media when people rank Folklore songs. So far, off of Midnights, I can’t really say what my favorite is because I feel like her songs take a while to sink in until I pick. When I first listened to it, I liked You’re On Your Own Kid and Midnight Rain. Now I’m starting to like Maroon and Sweet Nothing. Anyway, it was great seeing your descriptions and interpretations of each song!
Hey Ivy! I have to admit, I am not a die hard Taylor fan nor am well versed in her songs, however some of them are nostalgic to me. With the hype about her recently, I saw your blog as an opportunity to develop my Swifty spirit. I also really enjoyed how you gave suggestions on things to do while listening to any given song, not only is it helpful, it gives more information about the vibe of each song. All Too Well, the 10 min version, is something I usually get bored listening to, but with your breakdown of the lyrics, I am happy to give it another go. I vividly remember listening to Style for the first time and was like, “is this really T-swift?” because it was the first time I ever heard her sing pop like that. I feel like 1989 was a revolution for her. I will definitely give Cardigan a listen, and I will definitely be more attentive to the versus rather than the chorus. Tis the Damn Season will definately be my next listen, especially since ‘tis the damn season (right after the spooky season is over). Also contemplating what a hom town means when you leave is especially relevant to all of us right now… Overall, I love the unique and vivid imagery that you immerse this piece with, making for a very aesthetic read, if I can use that word in that way.
Hello Ivy, I LOVE THIS BLOG POST! Yes, I am a taylor swift fan, and I am proud. Personally, I think midngights is so underrated…like all her lyrics are so relatable and they make me feel a certain way. My favorite are anti hero, maroon, snow on the beach, labyrinth, dear reader. Okay I love how you put all to well first…like duh. I didn’t think it was possible to love a song so much that is 10 MINUTES LONG, but it is. Have you watch the music video for all too well…i can’t even put into words how I feel about it. I love how you put “listen while”…because there is taylor swift for every mood and feeling. Style explained how I imagined my life in the future as a child…I felt so boujee listening. I like cardigan..but I think it is really overrated. Yes its the damn season is so underrated, this song explains nostalgia during the fall and winter 100%! I agree with Mine, I always think of false happy scenarios to that song and it honestly can make my bad day turn around. I love all of these but where is the classic you belong with me, tears ricochet, this is me trying, the 1, our song. Overall, LOVED this post!