In 2008, Taylor Swift’s world (and our world, let’s be honest) was forever changed with the release of her sophomore album Fearless. At the age of 20! years! old! she won Album of the Year, the youngest ever until it was broken by Billie Eilish last year.
Flash forward 13 years later, and she is now one of the biggest stars in the world… which doesn’t mean anything when it comes to owning her work. Unfortunately, the blood, sweat, and tears that she put into her master recordings are not owned by her, but she has done what she does best and used what the outside world throws at her and pivoted to make her even stronger. And in less than a month from now, Fearless (Taylor’s Version) will be gracing our ears and reminding us that when it comes to Taylor Swift, you should always bet on her to come out on top.
With the re-release coming in less than a month now, I thought it’d be fun to rank her songs on this album. Fearless is one of my favourite albums of hers–there are just so many quality songs–so it’ll be interesting to see how this one shakes out.
(Be warned: long post ahead!)
This song is the definition of… execution failing intention.
I love a song that’s not about love. I love love songs, but I love songs that aren’t about love, and Taylor has a lot of those that are really, really solid. It has a really excellent meaning with Taylor not being sure if she would be able to achieve success with her small label that will not be named, which is adorable because this album made her incredibly famous. The poetry of her waiting to finish the song until something big happened in her career is chef’s kiss.
Yet the musical sound of the song falls flat for me, and I don’t think I’ve ever listened to it since the first time I heard it. Thankfully, Taylor has many songs in her repertoire and wrote a wonderful, updated version of this song on Speak Now called Long Live. You were an important part of Taylor’s musical journey, Change, and for that you are appreciated, but nothing more than that.
12. Tell Me Why
I’m a firm believer that Taylor’s earlier stuff still stands the test of time, but this is not one of those songs. The country is a little too country for me, enough for me to think it would’ve suited her debut album better. Additionally, the lyrics are nothing to write home about, but I forgive her because she was still finding her footing.
I mean, maybe it’s because I’ve never been cheated on. I’m sure that adds to the emotion of the song.
11. Forever & Always
The infamous Joe Jonas song that she added a few days before the album was due.
I’m not crazy about the song. It’s fine, but I never catch myself listening to it. That being said, I do have to knock off many points (like another song) because the piano version is much better. I don’t know if I’m against Taylor doing rock-y songs, or if it’s because I love acoustic/instrumental versions of songs, but I just don’t think this works better as an angry song than a sad song. Though you could argue that they’re both sides of the same coin of feeling hurt.
10. The Way I Loved You
This is one of those songs which wins in the concept department, but the lyrics and music could use some work. Which is fine, this was at the beginning of her career and she was a teenager.
It’s a funny mystery of love: why are bad boys so popular? What is it about nice boys that got them the ‘nice boys finish last’ phrase? I don’t know, but it’s something that’s despaired me enough when I’ve liked guys who were not good. Why do we do that, ladies? Much to think about.
9. Hey Stephen
It’s a cute and simple song, not memorable enough in music or lyrics to be a stand out, but serviceable when the moment calls for it. It’s definitely a song I play in the early days of having a crush, when you feel all giggly and you’re dreaming about happy days together. Nothing serious, but not all loves have to be.
8. You’re Not Sorry
I do like a good ballad, especially a slightly angry ballad, which this one is. It’s something that I admire about Miss Swift–she doesn’t seem to have too much trouble saying goodbye if you crossed her, no matter how in love with you she was. I waffle back and forth too much when I cut people off.
I’m not sure how I feel about the rock aspect of this song. On one hand, it makes it more dramatic, which is a plus, but on the other hand, I really really love the piano version of this song. I think it works better as a sad song instead of a power ballad. (Side note: The piano version isn’t official, but it should be.)
7. The Best Day
Listen, it’s around this point that I feel bad for ranking songs so low–but it’s not because The Best Day is bad, it’s just because there are so many good songs on this album.
The Best Day is adorable, sweet, quaint, and I love that this song exists. I love that she has such a close relationship with her mother, affectionately known as Mama Swift, and I love that her mother raised her to be such a wonderful woman, and I love that she surprised her mom with this song for Mother’s Day. What I hate is that her mother has cancer, and that Soon You’ll Get Better became a sequel to this song. It’s just… tears.
6. White Horse
I’m a dramatic person, but so is Miss Swift, which is incredibly validating for me.
So the story behind this song being one where you thought you were in a movie kind of love only to realise that you’re in this stinky real world… hits hard. You thought your love was the kind of love that movies and books and legacies were made of, but it turns out that it was really just a random dalliance that nobody will remember. You’re heartbroken, sure, but you also feel stupid and let down and embarrassed. White Horse perfectly encapsulates those feelings.
It’s funny to think about this song being written from the perspective of a teenager, because you’re so young but you’re already having to push yourself into being brave with falling in love. Still, youth doesn’t make the message any less universal, which is that there are a great number of things in this world that require trust and bravery, and you just need to commit and see it through. Love being one of them.
I love how this song sounds the way it feels, which is one of the best parts about combining music and words in songs. There is a bright but still mellow undertone to the song, which reminds me of a girl trying to act cool but somewhat failing because she’s falling in love. I’m sure we’ve all been there.
You can bet I walked into high school with this playing in my earphones. I’m corny like that (when I went to New York a few years ago, I also listened to Welcome to New York. There’s a fact that you didn’t need, or want, to know).
Now that I am a few years removed from fifteen (okay, many years), this song makes me emotional to listen to. High school was a turbulent time for me, very much the lowest period of my life, and listening to this song reminds me of being a teenager, lost and confused on your place in the world. Really, all you want to do is fit in, but that’s not an easy feeling to grasp.
But what Taylor sings later in the song is true: there is life after high school, and you will do bigger things in life than the things you do in high school. Did I ever think I would be in medical school at 21? No, absolutely not.
3. Breathe (ft. Colbie Caillat)
I’m going to be honest and admit that I was really ignorant as a kid, because I didn’t understand the albums had songs other than singles until I was like… 12. That is to say, I didn’t discover Breathe until I was in high school or something, which was at least five years after Fearless came out.
The song is quite understated, with little tonal variation, but that quiet factor is what makes it all the more devastating. Sometimes heartbreak rips out your heart and you want to scream and cry, but sometimes it is shocking and you are left stunned and still.
This song has a special place in my heart because I listened to it over and over after an absolutely heartbreaking falling out with a friend. I was pleasantly surprised to learn that Taylor wrote it about a friend instead of a romantic interest. Her ability to write about many different emotions in life is one of her biggest strengths, and it’s expertly showcased here.
2. You Belong with Me
It’s interesting to see how music videos can really tie themselves into a song, and for me, You Belong with Me will always remind me of that adorable high school neighbour-next-door music video featuring Hannah Montana actor Lucas Till. Everything about the music video is iconic: the signs, the t-shirt, brunette Taylor Swift being the enemy, the glasses-off-girl-is-cute moment at the dance, the cute signs saying “I love you” (a little weird because he had a girlfriend the whole time, but whatever).
It was the perfect follow up single to Love Story, really cementing Taylor as the relatable girl next door who just happened to write catchy songs about our own crushes and heartbreak.
1. Love Story
The song that propelled her to success and the song that I first heard of hers. In hindsight it was so obvious that she would release the… re-release of this song first.
The song is so unbelievably catchy with a compelling story and a gorgeous music video to boot. You can bet I belted out “Romeo, take me somewhere we can be alone” as a nine-year-old and also when the re-release came out. It’s her most famous song for a reason, and deservedly so. It’s just a solid song all the way through, with wonderful references to great works of English literature to boot.
That was a doozy of a post to write, but really fun too. I listened to Fearless while writing this post and I was reminded of what a great album it was once again. I can’t wait to listen to Fearless (Taylor’s Version) on April 9th, and can guarantee that it’ll make me feel like I was nine years old and discovering the force that is Taylor Swift for the first time. I miss the better days.
Let me know what your ranking for Fearless is! I’d be happy to hear different people’s opinions on such a strong album.