I’ve been a Taylor Swift fans since “Tim McGraw.” I will never forget where I was when I heard that song: the basement of UVA Medical Center, bored out of my mind working in a medical records job, streaming a country music Pandora station while I pushed papers around and daydreamed about the day I’d be living in Nashville and writing about the artists I listened to. It was in the days before Spotify, so I had to jot down names of songs I heard and liked, then go in search of them on places like MySpace and Limewire (I’m not proud, but don’t tell me you didn’t pirate music too way back when).
Taylor’s debut album came out soon after. I snatched it up and fell in love with nearly every song, particularly “Picture to Burn” and “Should’ve Said No.” A few weeks later, my mom, Aunt Lisa, and I went to see George Strait in Charlottesville. Taylor opened for him. Very few people in the crowd knew who the cute little blonde teenager in sequins was, but they all thought she was “precious” or “adorable.” No one paid her any mind when she walked out of the backstage tunnel to watch George’s set.
Within the year, she had become a household name.
And in my opinion? She gets better with every album.
I was listening to evermore the other day when I had the idea to rank my favorite Taylor Swift songs, a lofty goal given there are oh, two hundred or so, give or take, to choose from. But after MUCH hemming and hawing, I did it.
Here are my Top 25 best Taylor Swift songs.
- “All Too Well” – Taylor’s best song. The lyrics are perfection. She entangles you in a memory that is so vivid it feels like you’re there, living through it with her. There are so many lines that are just *chef’s kiss* that it’s hard to pick the best, but “after plaid shirt days and nights when you made me your own, now you mail back my things and I walk home alone” is one that always strikes me. The 10 minute version will be available on her re-recording of Red and I cannot wait to be in my feels with it on repeat.
- “invisible string” – I believe in the idea of an invisible string tying “it” all together, and this song is the anthem for that belief. The lyrics are almost bouncy as they ponder the idea of life pulling the strings to ensure our fated moments – like falling in love – come to fruition. It’s a well-crafted, beautiful song that only furthers my belief that everything happens for a reason.
- “Lover” – This will be my first dance song when I get married. It’s dreamy and romantic and each time I hear it, I imagine myself waltzing on the dance floor with my husband in my wedding dress. Leaving the Christmas lights up until January, friends crashing in the living room… A love song rooted in reality.
- “Wildest Dreams” – This is a sexy, sweeping power ballad that brings to mind the image of passion-filled nights and a romance that is destined to be short-lived but memorable. It’s one I crank up in the car and belt out without apology. Imagine my delight when she released the “Taylor’s Version” as I was writing this post.
- “Mean” – As someone who has made bold choices in their life to buck the status quo and chase big dreams, this song is my anthem. You get a lot of whispers behind your back when you’re out there living your life. You’re the subject of many gossip sessions. But when Taylor sings “someday, I’ll be living in a big ‘ol city, and all you’re ever gonna be is mean,” I just say YES GIRL and keep living my life – in a big ‘ol city.
- “The Archer” – Confession: I didn’t like this song for a while. But then I heard a live version of it and it changed something in me. I love the dichotomy of it. “Who could ever leave me, darling? But who could stay?” I also love that it ends on a hopeful note: “You could stay.” It somehow became a favorite before I realized it had happened.
- “Fifteen” – Who hasn’t lived this song? We think the world revolves around us as teenagers. We’re gullible, vulnerable. Being a teenager is hard and this song details that. The line “I swore I was going to marry him someday, but I realized some bigger dreams of mine” hits me right in the gut every time because I most certainly swore I was going to marry “him” someday – and I am so glad I didn’t.
- “White Horse” – Another song we have all lived. We all know that relationship that should have ended, but we just struggle to let it go. This song is about that – and about finally letting go and moving on – despite its fairytale vibe. “It’s too late for you and your white horse to come around.” Yes, yes it is.
- “betty” – There is so much to love about “betty,” including the fact that Taylor name checks Blake Lively and Ryan Reynold’s kids. It’s about a teenage boy losing the love of his life due to his mistakes, but the storytelling is so well-done that it can be imagined from any perspective and any identity which me love it that much more. I have a sticker that says “Betty says gay rights” and yep – what Betty says.
- “the last great american dynasty” – It’s about a real life woman named Rebekah Harkness, a St. Louis heiress who married Bill Harness. Rebekah truly had a “marvelous time” after Bill’s death, throwing parties, spending money, and upending her quiet neighborhood. She was also a former owner of Taylor’s Rhode Island mansion. I love the rebellious nature of this song, and have some of the lyrics – “there goes the loudest woman this town has ever seen. She had a marvelous time ruining everything. She had a marvelous time” – framed on my wall. I like to think I channel a bit of that rebellious spirit every time I hear that song or walk by my framed lyrics. (See my prints on Instagram)
- “ivy” – It’s a song about an illicit affair – or is it about her feud with Scooter Braun as some fans believe? I choose to believe its about an affair. The chorus – “my pain fits in the palm of your freezing hands” – really does it for me on this song. And I still get a kick out of Taylor dropping cuss words as someone who has followed her since she was a mere fifteen year old in sequins who introduced herself as “Hi, I’m Taylor!”
- “Back To December” – What makes this song special is that it’s Taylor taking responsibility for the end of a relationship. Rumor is this song is about Taylor Lautner and I can see it (it’s the “tan skin” line that gives it away). I love the honesty and regret laced throughout the lyrics. I also saw her perform it live backed by an orchestra on the Speak Now Tour and it was a MOMENT.
- “champagne problems” – This piano ballad is so real life in my opinion. It’s about two people who realize they are on different paths. He wants to get married, she wants to be free. There’s a failed engagement, a preemptive celebration, and the wish that he will “find the real thing instead,” someone who will patch up the “tapestry that I shred.”
- “Cornelia Street” – Nostalgia of a place and time sums up this song. It’s recalling moments and memories that took place along a street during a certain point in time, the start of a relationship, the rough patches, the good and the bad. We all have those place that evoke strong memories. This song is about those locations.
- “Daylight” – This song is about putting down our “cloaks and daggers” and moving on. Letting go of the past, of mistakes, of hurts, and walking into daylight, into a new day, a new opportunity. It’s about realizing you have been unlucky in the past or made mistakes, but also finding the strength to admit you were wrong and the courage to move on. It’s another one I fell in love with after hearing a live version.
- “Delicate” – I love how this song starts. “This ain’t for the best. My reputation’s never been worse but, you must like me for me. We can’t make any promises now can we babe? But you can make me a drink.” It’s about the insecurity that comes with putting yourself out there in a new relationship, worrying that the other person might not like you or in Taylor’s case, be turned off by her tarnished reputation.
- “exile” – I have to be in the right mood for “Exile,” but the lyrics are just so stunning and the points of view bouncing between her to Bon Iver as they navigate life post breakup is well-done. “I think I’ve seen this film before, and I didn’t like the ending” is a brilliant lyric.
- “no body, no crime” – When I heard “no body, no crime” on evermore, I actually yelled out “YES GIRL!” It’s a moody tune that harkens back to Taylor’s country days and the story it tells is one of revenge I can get behind. I crank this one up every time it comes across my playlist.
- “‘tis the damn season” – I’ve lived this song. It’s about returning to your hometown and seeing that person from your past again. You know it’s not going to go anywhere, but there’s comfort in the nostalgia. It’s emotional, a bit of a gut-punch, and yet still has this level of comfort that wears like your favorite flannel. Fun fact: a line from it inspired the first feature film I wrote: “The road not taken looks real good now.”
- “You’re Not Sorry” – I always feel a sense of girl power when I listen to “You’re Not Sorry.” It’s about that moment when you finally realize the person who keeps hurting you is never going to change and you find the courage to say “you’re NOT sorry” and leave them in the dust. Again, I’ve been there.
- “New Year’s Day” – This is such a simple song, yet the lyrics paint a lovely picture of waking up on New Year’s Day to a floor covered in glitter and empty champagne bottles after a night of celebration, the love of your life by your side. My favorite line though? “I’ll be there if you’re the toast of the town babe, or if you strike out and you’re crawling home.”
- “mirrorball” – You can’t help but listen to this song and not imagine yourself spinning under a disco ball. It’s about how someone (Taylor herself) has many sides and while some may be pretty to look at, they’re also fragile. “you’ll find me on my tallest tiptoes, spinning in my highest heels” really does just speak to that disco ball dance.
- “Mine” – “Mine” has one of the best lyrics in all of Taylor’s catalog: “You made a rebel of a careless man’s careful daughter.” Wow. There are so many great lines in this song – “I was a flight risk with a fear of falling” – and it’s so catchy with a bit of a Romeo & Juliet undertone to it.
- “Love Story” – The ultimate fairy tale romance song. I was an intern when this was released and I fell in love with it right there at my desk. We had the exclusive video premiere too and I felt oh so special for getting to see it before it’s official release. Everything about it was magical and when she released the re-recording earlier this year, I was right back there in those “Love Story” moments.
- “Holy Ground” – Some may consider this a bit of a deep cut, but “Holy Ground” has always been one of my most-played Taylor songs. “Spinning like a girl in a brand new dress” just puts me in a good mood and makes me feel like dancing.
While I could go on and on, I’ll stop there with my Top 25 Taylor Swift songs. Except… I’ll round it out with an event thirty by giving you five bonus songs and one sentence as to why I love them. I just can’t help it…
- “Sparks Fly” – It’s a magical song about love at first sight.
- “Tim McGraw” – Taylor’s debut single is legendary and I’ll never forget her walking off the stage at the ACMs to serenade the actual Tim McGraw.
- “Our Song” – The way the chorus describes a series of sounds – slamming screen door… tapping on your window… that make up a couple’s son is just brilliant.
- “mad woman” – Taylor got the last word in the Scooter Braun/Big Machine drama.
- “The Way I Loved You” – It’s a big ballad that I love to belt out when I’m alone in my car.
What’s your favorite Taylor Swift song?