Taylor Swift Fearless Artwork
Taylor Swift Stanning

Tay-Tay Top Five: Fearless

Okay, so before I get into this I want to clarify something. Today, I’m talking about the initial release of Fearless. I appreciate that we have recently seen the release of Fearless (Taylor’s Version), and I admit right off the bat that it is far superior than this one. However, I felt it was still important to talk about the initial release, as this was the first Taylor Swift album I ever discovered. While I didn’t become a fully converted Swiftie until the 1989 era, this was essentially the start of me discovering her music. Not only that, but as you’ll see when I come to publishing the post on Taylor’s Version, my top five songs also differ slightly. Plus, there are so many differences between the two albums, and given the contextual differences between them, it would be unfair for me to write about them in the same post. I want to give Taylor’s Version the attention it deserves, but I also didn’t want to ignore the original version of Fearless – not only that, but I’ve already covered the original releases of the albums Taylor will ultimately be re-recording, and my neurotic ass cannot bear to leave any gaps. It takes several blocks out of my mental Jenga. Anyway, I’ve explained myself enough, let’s crack on.

Pinterest artwork for Fearless by Taylor Swift


So, Taylor Swift’s Fearless was her second studio album and it continues with the country style sound that’s so prominent in her debut album. It largely explores the theme of teenage love and heartbreak, and was released when Taylor was just 19. At 19 I was crying and regretting choosing Northampton to study my degree. Just saying. According to The Telegraph, Fearless is the most awarded album in the history of country music, and when Taylor won the 2010 Grammy Award for Album of the Year at just 20 years old, she became the youngest artist to win the award (surpassing Alanis Morrissette’s Jagged Little Pill, which won her the award when she was 21). She held this title up until 2020, when she was surpassed by Billie Eilish, who won the award at the age of 18.

Album Stats

Information correct at time of writing. 

Release Date: 11th November 2008

Producers: Nathan Chapman, Taylor Swift

Label: Big Machine Records

Tracks: 13 (16 on International edition, 19 on Platinum edition)

Awards & Nominations: 
Canadian Country Music Association – Top Selling Album 2009 (Won)
Country Music Association Awards – Album of the Year 2009 (Won)
Academy of Country Music Awards – Album of the Year 2009 (Won)
American Music Awards – Favourite Country Album 2009 (Won) and Favourite Pop/Rock Album (Nominated)
Teen Choice Awards – Choice Female Album 2009 (Won)
SirusXM Indie Awards – International Album of the Year 2009 (Won)
Canadian Country Music Association – Top Selling Album 2010 (Won)
Juno Award – International Album of the Year 2010 (Won)
Grammy Awards – Album of the Year 2010 (Won) and Best Country Album 2010 (Won)

Taylor Swift - Fearless Album Artwork

Image and Information Source: Wikipedia

My Top Five

  • The Best Day
  • Fifteen
  • You Belong With Me
  • Change
  • White Horse

Honourable Mentions: Love Story, Breathe, Fearless

The Best Day

The Best Day is one of the Taylor Swift songs I discovered a lot later on. In fact, I don’t think I even truly appreciated it when I first heard the album as a whole. It wasn’t until a few years ago that I properly listened to the lyrics, and out of curiosity did a little research on them, and found out that it’s a dedication to her mother, Andrea Swift. I’ve mentioned before that this particular song reminds me of the good times with my Mum, and in particular, the second verse really resonates with me. In an interview with GQ, Taylor talks about an incident with some girls at school who snubbed her, and how her mother helped her escape these sorts of situations. I related a lot to this and experienced similar problems at school, and I remember my Mum always being in my corner, especially on the days where I’d come home crying because I wasn’t invited to this stupid sleepover or that dumbass birthday party. She was, and still is, my best friend, and every time I hear this song, particularly this verse, I think of her:

“I’m thirteen now and don’t know how my friends can be so mean
I come home crying and you hold me tight and grab the keys
And we drive and drive until we’ve found a town far enough away
And we talk and window shop ‘til I’ve forgotten all their names
I don’t know who I’m gonna talk to now at school
But I know I’m laughing in the car ride home with you
Don’t know how long it’s gonna take to feel okay
But I know I had the best day with you today.”


Fifteen is one of those songs on the Fearless tracklist that just gets me right in the feels. On the days when I’m feeling particularly emotional, it will have me crying in my car. The song is based on Taylor’s Freshman year at high school, meeting her best friend Abigail Anderson, and how they both got their hearts broken. For me it drums of memories of being fifteen at school and thinking you know everything, and in my case, spending way too much time worrying that I’d never get a boyfriend. It’s one of those songs you wish you could have heard at that age (admittedly, the album was released in 2008 when I was sixteen, but let’s face it, at sixteen, you don’t give a crap about song lyrics), and when my grown-up ass listens to it at the age of 29, it takes me back and makes me want to give that little wonky toothed speccy kid a hug and tell her that she’s fine, she doesn’t need a boyfriend just because all her friends have one, and that if she just waits a smidge longer, she’ll find the best boyfriend who will ultimately be the person she ends up marrying.

You Belong With Me

This is an absolute banger. While her songwriting talents over the years have proven no bounds, there’s no denying that back in the day, she wrote some bloody good songs over out-of-reach love interests. It’s one of my favourite songs to belt out when I’m driving and it always cheers me up – which is weird when you consider it’s about an unrequited love for someone – but at the end of the day, how can you be sad when you’re screaming “CAN’T YOU SEE THAT I’M THE ONE WHO UNDERSTANDS YOU, BEEN HERE ALL ALONG SO WHY CAN’T YOU SEEEEEEEEE YOU BELONG WITH MEEEEEEE…” just me? Okay then. 


Change is one of those songs that’s perfect for listening to when you need a bit of a kick up the butt. The song talks of overcoming obstacles and was written in the early days of when Taylor was signed to Big Machine Records, which at the time was a new, small record label. She left the track dormant until she won the Horizon Award at the 2007 Country Music Association Awards, and it was completed the day after. Of course I don’t want to ignore the future drama that occurred with Big Machine Records, ultimately leading us to the re-recording of Taylor’s albums – believe me, I have more to say on the issue when I do my post on Fearless (Taylor’s Version) – however, looking back on this particular song, which I first heard when I was sixteen, it was something I needed to hear. A song about overcoming obstacles and reaching success is the perfect soundtrack when you’re studying for your A levels, and I remember this being part of my revision playlist.

White Horse

Probably one of my favourite “break-up” songs that Taylor has written. The song draws a contrast with Love Story, both of which use fairytale imagery, and was allegedly inspired by the same person, the focus of the song being the moment you discover a person isn’t who you first thought them to be. I’ve mentioned before that I’ve been lucky enough to never have gone through as song-writing-worthy break-up (although I may or may not have had this on my angst playlist which I listened to whenever Liam and I had a row…), but even without that experience, there’s no denying that White Horse really gets you in the feels, especially this line in the final chorus –

“I’m not your princess, this ain’t a fairytale,
I’m gonna find someone someday who might actually treat me well”

Honourable Mentions

When it comes to honourable mentions, I have to start with Love Story. It was the first song of Taylor’s that I ever heard, and I remember loving it even that first time around. I loved the music video, I loved the lyrics, I loved the hopeless romanticism in the song, and that key change in the final chorus – I think there’s one thing that sums it up:

Inhaling seagull meme with Love Story lyrics applied.

I also love Fearless – it’s just a happy and upbeat song that kicks off the album perfectly and captures the excitement of a new relationship. Then you’ve got Breathe, featuring Colbie Callait, which is composed of this gorgeous string arrangement and puts me in mind of one or two friendships that haven’t quite worked out over the years. On top of that, both Taylor and Colbie’s vocals compliment one another perfectly.

Final Thoughts

There’s no denying that Fearless by Taylor Swift is the album that cemented her breakthrough into the music scene, and it’s packed with some gorgeous lyrics proving what a talented songwriter she is, even when she was at such a young age. While the album has since moved on after the recent release of the re-recording, the initial release of the album will always stick with me as it reminds me of when I first discovered her music. In fact, I feel that particular memory is what makes Taylor’s Version all the more special.

What did you think of the initial release of Taylor Swift’s Fearless album? 

Catch Up with the Rest of My Tay-Tay Top Five Series

Red (Taylor’s Version) (2021)
Fearless (Taylor’s Version) (2021)
Evermore (2020)
Folklore – The Long Pond Studio Sessions (2020)
Folklore (2020)
Lover (2019)
Reputation (2017)
1989 (2014)
Red (2012)
Speak Now (2010)

Taylor Swift (2006)

Image credit: Pitchfork

11 thoughts on “Tay-Tay Top Five: Fearless”

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