The Ultimate Taylor Swift Song Break Down

As we are knee-deep in the reputation season, and as the day I get to see my favorite gal blow my mind performing her amazing songs approaches, I thought I’d evaluate all of T-Swift’s songs, ranking some of my favorites off of each album.

A couple months ago my mom sent me a “special collectors edition” Rolling Stone magazine, including every profile piece they have written on Taylor throughout her career, as well as a giant ranking of all 129 of her songs. (Shoutout to my mom for knowing me all too well…)

129 songs is very ambitious, so I’m going to list my top 5 songs off of every album, along with lyrics that make them a top contender.

Taylor Swift, 2006

Ah, the album that started it all: Sassy, country Taylor with her frizzy, curly hair.

5. Picture to Burn

Full of rage, sass, and country twang, Taylor proves her distaste in an ex through these pointed lyrics. Definitely a jam to sing in the car with friends.

Best Line: “Watch me strike a match on all my wasted time.”

4. Tim McGraw

This country ballad was Taylor’s first single released, and such a classic. An endearing way to remember a past summer love, she reminisces about dancing in the moonlight by the lake, and her favorite items of clothing, naturally.

Best Line: “When you think happiness/I hope you think that little black dress.”

3. Should’ve Said No

This rock country song proves from the start Taylor won’t stand for the bullsh*t from boys. Sorry, bud, she’s not taking you back.

Best Line: “I shouldn’t be asking myself why/You shouldn’t be begging for forgiveness at my feet.”

2. Teardrops on my Guitar

What a heartfelt tune about a high school girl crushing on her guy friend who loves another girl. Ugh. Don’t worry, Tay, I’m sure Drew is regretting not asking you to prom now.

Best Line: “I’ll bet she’s beautiful/That girl he talks about/And she’s got everything that I have to live without.”

1. Our Song

What. A. Jam. You can’t help but smile and scream the words to this song when it comes on (I know I do). An upbeat jam about young, innocent love. Sigh.

Best Line: “Our song is a slamming screen door/Sneaking out late and tapping on your window/When we’re on the phone and you talk real slow/’Cause it’s late and your momma don’t know.”

Fearless, 2008

This album was initially what made me fall in love with Taylor and her music. I was in middle school, and all of her nerdy/hopeful/romantic lyrics had me relating and feeling at ease that someone else was feeling the same way.

5. The Best Day

This song, about all of the sweet memories Taylor has made with her mom, gets me emotional to this day. Grade school is hard, and kids are really mean, and like Taylor, my mom was always there for me. Things are confusing and unsure, but my mother was always there and that never changed.

Best Line: “I don’t know who I’m gonna talk to now at school/But I know I’m laughing on the car ride home with you.”

4. Hey Stephen

Confession: I definitely wrote songs about my crushes in middle school (not nearly as good as Taylor’s), and this song was along the lines of something I would write.

Best Line: “All those other girls/Well they’re beautiful/But would they write a song for you?”

3. Fearless

A song that defines this Taylor Swift era, for obvious reasons. It’s up-beat, feel-good, and makes me want to twirl around in a dress with my hair down. (Which I have done, multiple times. Mostly in the kitchen, at my parent’s house, in middle school, high school, and winter breaks throughout college.)

Best Line: “And I don’t know how it gets better than this.”

2. You Belong With Me

From a girl who was too awkward and ~quirky~ for boys to like in middle and high school, this song was my ANTHEM. Unfortunately for me, none of them ended up meeting me at the prom with a hand-written sign saying they loved me, too, but hey, it’s still a jam, and I’ll always be the girl in a tee shirt on the bleachers, who occasionally sings into a brush in her room. (All the time, actually.)

Best Line: “Can’t you see that I’m the one who understands you/Been here all along so why can’t you see/You belong with me.”

1. Fifteen

If I’m keeping it 100 with y’all, I teared up in the car yesterday listening to this song. It honestly captures the essence of being a young teenager, feeling all the things you do, thinking everything is life or death, thinking you are in love, thinking you will die if he doesn’t love you back. And then the feeling of looking back and seeing that, “you’ll do things greater than dating the boy on the football team.” A LITTLE LOUDER FOR THE PEOPLE IN THE BACK.

Best Line: “Back then I swore I was gonna marry him someday but I realized some bigger dreams of mine.”

Speak Now, 2010

I have sweet memories of listening to this CD non-stop in my mom’s car, to and from school, to and from rehearsal, we would jam to all of these songs. It’s a teenager’s take on life, from falling in love, getting your heart broken, dealing with the ~haters~, and moving on from mistakes.

5. Never Grow Up

I know I said this was mainly listened to in high school, but this song came to mean a lot to me once I moved to a new city 12 hours away from home after high school. The feeling of missing home, but knowing you’re where you need to be, brings on the feeling of wishing you had never grown up in the first place. This song captures the feeling of missing childhood simplicity and magic, in a lovely way, of course.

Best Line: “Don’t lose the way that you danced around in your pjs getting ready for school.”

4. Speak Now

This song has some fun memories associated with it, one of them being a project I did in 8th grade. We had to choose a poem to create a video for, demonstrating some of the lines of the poem. I convinced my teacher that yes, this Taylor Swift song IS a poem, and after some consideration, she gave in, and I had the best day of my middle school career sitting in the computer lab with my headphones in, listening to Taylor Swift, making a lyric video.

Best Line: “She floats down the isle like a pageant queen/But I know you wish it was me/You wish it was me/Don’t ya?”

3. Mine

This song is a sweet story of a girl falling in love in her early twenties, while she’s still figuring things out, and despite her fears and her baggage, makes it work with a guy who is willing to take the time to understand and love her. Wow, sounds nice. She also dances in the forest around hanging pictures of her and her bae with flawless curly hair (practically a myth, seeing as that she is outdoors and in reality, that hair would be up in a messy bun in SECONDS. But it’s fine, good for her.)

Best Line: “You said, ‘I remember how we felt sitting by the water/And every time I look at you, it’s like the first time/I fell in love with a careless man’s careful daughter/She is the best thing that’s ever been mine.'”

2. Mean

This song has been the backbone of a lot of my feelings to many people throughout my life. The mean school kids, my freshman year design teacher who said I wouldn’t be a successful designer, people who laugh when I tell them I go to an art school. This song is great to not only vent about those ~haters~(who are mean, liars, and pathetic) but feel good about who you are, despite what people may say.

Best Line: “Someday I’ll be living in a big ‘ol city/And all you’re ever gonna be is mean.”

1. Dear John

This song has always gotten me in my feels, even more now that I’ve experienced a similar relationship to the one Taylor describes in the song. I love the way she builds the song, and the relationship, up: first being confused, trying to please a guy who can’t commit, is shady, and unsure how to express his feelings, blaming herself for the way she is feeling, saying she should’ve known, and then realizing, hey, it wasn’t okay that you treated me like sh*t, and you should’ve known. Yes, Tay. Yes.

Best Line(s): “You are an expert at ‘sorry’, and keeping 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.”

Red, 2012

When I began to list my top 5 songs for this album, I listed 11. That’s how amazing this album is. It’s raw, poetically stunning, and captures the feelings a young, twenty-something brilliantly. 10/10. Would highly recommend.

5. We Are Never Ever Getting Back Together

This was a jam before I went through a breakup and a JAM after. I think a lot of ladies can relate to lame ex boyfriends wanting to get back together, and Taylor captures this conversation perfectly with this humorous, up-beat piece.

Best Line: “Ugh, so he calls me up and he’s like, ‘I still love you’ and I’m like, just, this is exhausting, you know? Like we are never ever getting back together. Like ever.”

4. State of Grace

This song is not only catchy, but describes falling in love in your early twenties well (in my opinion). It’s fast and wild and free, and you both have a past and have pain, but that’s where the grace comes in, and you find yourself constantly in that state.

Best Line: “We fall in love ’til it hurts or bleeds or fades in time.” 

3. Red

This song pretty much sums up how it feels to love and lose in a relationship that, “like driving a new Maserati down a dead-end street”, is going nowhere and will most likely end in disaster. It captures the feeling of intensity, and trying to forget something that rocked your world. It’s poetic and catchy and I just love it.

Best Line: “Moving on from him is impossible/When I still see it all in my head/In burning red.”

2. 22

I didn’t understand how wonderful this song was until I got into my twenties and could relate to the content. It’s an anthem for early twenty-somethings trying to figure their life out, with an array of emotions, trying to stay positive and take it day-by-day. I’d like to point out that my parent’s got me a tee shirt saying, “Not a lot going on at the moment” for my birthday. If you don’t get the reference, feel my eye roll through the screen and go watch the music video to this song.

Best Line: “We’re happy, free, confused, and lonely in the best way/It’s miserable and magical.”

1. All Too Well

This. Song. All too real. It cuts me deep every time I listen. I think, being through a breakup and having been a disaster for a long time afterward, the hardest part is not the end, it’s not how things went wrong, but it’s the in-between. It’s the memories, memories of loving and laughing, memories of happiness, that cause so much pain in a breakup, and this song captures that truth. You want to move on, you know you have to, but the memories you know all too well are keeping you in a stand-still.

Best Line: “You call me up again just to break me like a promise/So casually cruel in the name of being honest/I’m a crumpled up piece of paper lying here/’Cause I remember it all too well.” 

1989, 2014

This album came out my senior year of high school, and man was it a treat. Pop Tay finally comes forward, guns blazing, as she officially transitions as a pop artist. Still excellent lyrics, with lots of fun beats.

5. Clean

I would always skip this song in high school, taking a liking to the more up-beat songs, but I’ve learned to really appreciate her lyrics in this song. It can apply to a lot of different scenarios, whether you are quitting a bad relationship, quitting a lifestyle, or just moving on to another phase in your life. This song describes how moving on and “getting clean” from something is a beautiful thing, even if it might not feel like that at first.

Best Line: “10 months sober/I must admit/Just because you’re clean don’t mean you don’t miss it.”

4. Shake It Off

This was the first single Taylor released off this album and a lot of people didn’t like it. Confronting the rumors people start about her, Taylor shakes and sings that “haters gonna hate”. You’re so right, T.

Fun fact: I took multiple drama classes in high school (yes, I was a drama kid), and one of the assignments was to choose a song and lip-sink perform it to the class on stage. I chose this song. It was the best day out of my high school career. I practiced in the kitchen to my mom. It was beautiful.

Best Line: “I’m dancing on my own/I’ll make the moves up as I go.”

3. Blank Space

Taylor is really getting it all out in the open about the rumors people spread about her on this album, one of them being how crazy she is in her serial dating. Good for her, turning the ridiculous stories into a brilliant song.

Best Line: “Darling I’m a nightmare dressed like a daydream.”

2. Style

This tune is about a couple who, no matter how much time goes by, and how many other loves they take in-between, never seem to go out of style. As Taylor describes this type of relationship, “it’s like a little black dress. No matter how much time goes by, that dress will always be in style.”

Best Line: “And I should just tell you to leave/’Cause I know exactly where it leads/But I watch us go round and round each time.”

1. Wildest Dreams

The first sexy Taylor song, about a good ‘ol fling. I love the heartbeat in the back, adding to the drama of the song. And I also love that Tay knows this dude won’t see her anywhere else except for his wildest dreams.

Best Line: “You’ll see me in hindsight/Tangled up with you all night/Burning it down/Someday when you leave me, I bet these memories follow you around.”

reputation, 2017

My. Baby. After years of waiting and hoping for another remarkable album, Taylor drops this golden child that changed our lives forever. Full of sexy lyrics and sick beats, this album is different from anything she has ever released, showing her range, talent, and amount of growth that has taken place, not only as an artist, but as a person.

5. King of My Heart

Okay, if I’m being honest, when the album first came out, this was not one of my favorites. But then one day I let it play in my car and thought, wait, this is a JAM. Just like the rest. The bridge is my favorite.

Best Line: “Up on the roof with a school girl crush/Drinking beer out of plastic cups.”

4. …Ready For It?

Number one trick to get me to come out of my shell at a party? Play this song. I get down. Like, okay Ms. Swift, YOU CLEAR THAT THROAT. Can’t even handle it. I ain’t ready for it.

Best Line: “Younger than my exes/But he act like such a man.”

3. Dress

I get butterflies every time I listen to this song. We all know how it feels to want to ruin the friendship with a hottie. We don’t want you as a best friend, boo.

Best Line: “Only bought this dress so you could take it off.”

2. Don’t Blame Me

Okay, I just listened to this song to see what I should say about it, and honestly, WHAT A JAM. I can’t help but nod my head and sway my body. The lyrics, the music, the mixing, it all makes this song so incredible. Tay takes us to church while preaching about being high on love.

Best Line: “For you I would fall from grace/Just to touch your face/If you walk away/I’d beg you on my knees to stay.”

1. Delicate

From the start, this has been my favorite song off the album. The subtle beginning, the beats, the lyrics. All of it makes me obsessed and want to put the song on repeat.

Best Line: “Sometimes when I look into your eyes/I pretend you’re mine all the damn time.”

Well guys, this article took literally all day to write, and I’m not upset about it. Looking back on all of these songs is like a time capsule. I have so many memories from each album, and how each song has made me feel throughout the years. Y’all, I’m seeing her live in a little over A WEEK and I have no chill. I love Tay. I love my mom for taking me to the concert and also listening to all of those albums and songs with me over the years. Stay tuned for the after post.