There’s something overwhelmingly nostalgic about Taylor Swift starting her album re-releases with my favorite album of all time, Fearless.
To understand the impact of this album, you have to understand my world in November of 2008. Back then, I was an awkward and overly imaginative 7th grader. And like most suburban teenagers, being a Taylor Swift stan (back when the word’s biggest claim to fame was the Eminem song) was the norm. Taylor’s lyrics were posted cryptically on Facebook or profile songs on MySpace. We knew the ins and out of Taylor’s chaotic dating life, and her recent interviews ruled the conversations at lunchtime. I even had one of her dresses from her Walmart fashion line.
In 2008, my young life was not the best. Like I said, I was awkward. And I often felt out of place at school. I was socially isolated and found it hard to relate to my surroundings.
So music provided escapism. I could listen to Britney and pretend to be a diva. When I played Beyonce, I could get the confidence to perform. When I listened to Christina on the car rides to school, I would dramatically lipsync the lyrics like I was my generation’s greatest vocalist.
A lover of storytelling and reading, Taylor’s music just fed into that interest. Her music allowed me to dream. It was reminiscent of the wanderlust that was peddled in every 2000s teen movie. Each song was like a mini-movie and gave me something relatable or something to aspire to. It’s what solidified me as a fan of Taylor’s music, which back then was still straddling the line between country and mainstream pop. I remember my dad being very confused when I picked up Fearless when it came out.
Being alive and aware during the original Fearless era made this re-release feel surreal. Especially considering I felt disconnected with Taylor’s music up until last year’s release of Folklore. To me, re-visiting Fearless was a perfect choice. After all, it’s the album from her discography that most resembles her latest work because it focuses on telling a story rather than dropping radio-friendly bops.
And while I consistently have listened to Fearless in its entirety since its release thirteen years ago, this refreshed version allowed me to re-live that moment in time. And remember why I’m a Taylor Swift fan in the first place.
Pressing play on the first track, I quickly remembered why it is in my Hall Of Fame of Taylor love songs. “Fearless” made me daydream of high school first dates. To this day, I don’t think of this song when I drive across the wet pavement after a storm. And listening to the re-recording made a flash of memories come at me.
Can’t lie. It made me tear up a bit.
Fearless dropped a little bit before I turned fifteen, and there’s some cathartic to have the experience of experiencing this song as a naive 12-year-old and as a 25-year-old. It hits different when you can really relate to the experience of getting lost in a fleeting moment that is your teenage years.
And when you understand the importance of giving grace to your younger self.
Yes, Taylor has done greater things than dating the boy on the football team.
“I’ve found time can heal most anything, and you may just find who you’re supposed to be.”
Fifteen, Taylor Swift
“White Horse” remains one of my favorites from Taylor’s discography. While it’s not on the same level as some of her more recent ballads, I think it’s important when we think of her evolution.
I still strongly remember the middle-aged mom sitting next to my dad and me at the Fearless tour who sat through the show passively until Taylor sang, “I’m gonna find someone someday/who might actually treat me well.” She lept to her feet and applauded in a way that only someone with the wisdom of age could.
It’s important to remember that a lot of discourse around Taylor at the time for Fearless’s release (and even now) was that she just wrote songs about boys. But now, as an adult, I can honestly say Taylor’s early work is not given proper credit for having feminist themes. Yes, there are songs on this album like “The Way I Love You” that glorify chaotic relationships. But a lot of the messaging in “White Horse,” “You’re Not Sorry,” and “Tell Me Why” encourages women to be strong in relationships and are definitely the predecessors for some of Taylor’s more overt female anthems.
This is a little ironic because the song that immediately follows “White Horse” is one of Taylor’s signature songs, “You Belong With Me.” It’s one of the many songs from Taylor’s discography to not age well. While I still sing this song with enthusiasm when it comes on in the car, I can acknowledge the not-like-other-girls trope promoted in the lyrics and music video.
I mean, this song gave me, the boyfriendless-cheerleading-band nerd a complex back in 2008.
But I do think it’s important to consider Taylor’s age when she wrote this song. Of course, a teenager wouldn’t have the maturity to understand the complexity that rejection of femininity doesn’t make someone a better partner.
Then there’s Breathe, which is another one of my top picks from Taylor. One that still works with an updated arrangement. I always loved that this song was about the end of a friendship. Back in the day, this song got me through the breakup of what I thought was a very close friendship. The haunting sound of Taylor and Colbie singing “I’m sorry” just gives me chills.
I actually have vivid memories of hearing “The Best Day” for the first time. It involved ugly tears. And I would be a full-on liar if I said I haven’t cried to the song within the last few months.
Songs about moms are a sure-fire way to trigger emotions. But “The Best Day” is a little too accurate when describing the relationship between mother and daughter. The song captures childhood innocence, the middle school trauma, and the appreciation that early adulthood brings.
For me, the second verse where Taylor describes her experience with bullying and her mother’s comfort summed up my daily experience at school. Like I mentioned before, I was having a tough time socially as my friendships crumbled apart, and I suddenly found myself on the outside (pun intended). And I can remember specific moments where my mom took time to make me feel better after a tough day at school. In fact, I had one of these days in the weeks before Fearless’s release (hence the ugly tears).
The vault tracks were a weird experience. They are dated – for sure. I remember some of them from the days when old Taylor Swift MySpace era songs were on YouTube (Justice for I’d Lie). Which is hard to believe considering Taylor’s music is under such lock and key these days.
These songs would’ve been big at the time of the original release or during the deluxe release (whew, imagine Mr. Perfectly fine during the J-14 era??) but would’ve faded into footnotes in Taylor’s discography.
Hearing these songs now, we can appreciate songwriting growth and gain more insight into Taylor’s mindset during this time. The vault songs don’t have hidden messages. We can’t create some big elaborate theory as to what A-List star was behind the lyrics. Similar to Folklore and evermore, these songs are just a spotlight on Taylor’s ability. After all, Fearless is the last Taylor album to be created without the cloud of mega-fame.
Which we can get from lyrics like “Talking ’bout your daddy’s farm we were gonna buy someday.”
In many ways, the vault songs are what brings this album full circle. For a moment, we get to go back into a simpler time to be a Taylor Swift.
While I still grapple with the reasoning behind Taylor Swift re-releasing her music (it’s the financial part for me), I can appreciate the bravery and dedication to step back into a time machine and go back to her early work. To me, this music doesn’t get the credit it deserves for being the catalyst for everything we now know about Taylor.
Like Taylor, I am older and wiser than I was in 2008. And this nostalgia ship makes me proud of my personal growth and even prouder of Taylor’s journey from curly-haired teen pop start to an adult who is still owning her craft and now her voice.
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