What Taylor Swift Means Now, Five Years After 'Fearless'

Fearless was not Taylor Swift's first album. She released a self-titled full length and two EPs before her sophomore album dropped on November 11, 2008. No, Fearless was not the beginning of Taylor Swift, musician. But it was the beginning of the Taylor Swift zeitgeist.

Before Fearless, Swift was still an opening act, albeit for some of country music's names. But after, she was not just country music's biggest name — she was a pop culture phenomenon. Fearless opened the floodgates for the curly-haired blonde girl from Nashville by way of Eastern Pennsylvania. Fearless set records for Taylor Swift and won her awards. Fearless made her dating life a national spectacle. Fearless introduced us to the Taylor Swift Experience. Today, the album is five years old, and it means something very different than when it was released. Or rather, Taylor Swift means something very different in 2013 than Taylor Swift in 2008. Maybe it's as simple as her straightening her hair. Maybe not. It's more than just Taylor Swift grew up. Listening to Fearless now — it's a broken promise, an unfulfilled dream.

It's a Love Story

Taylor Swift was 18 years old when Fearless debuted at #1 on the Billboard charts. It would end up spending a full year straight in the top 10, be certified six times platinum, and win Album of the Year at the Grammys, making Swift the youngest person ever to take home the title.

The world fell in love with Taylor Swift, and it's not hard to see why. She was talented, charming, and wholesome — the epitome of the girl next door you'd been crushing on. The love songs she sang were the love songs you wanted to sing her (or have sung to you by your own prince charming). At 18, Taylor Swift was gawky perfection. She was the Manic Pixie Dream Girl of top-40 radio. Her awkwardness was adorable, and sellable, before America got tired of the adorkable shtick (there's a reason she was on an episode of New Girl).

Most notably, though, was what she wasn't. "A button-cute blonde teen with a pocket full of hits," the Entertainment Weekly review of Fearless begins. Sound familiar? Swift was not the first blonde girl of the decade to take pop culture by storm. But as EW notes a few sentences later, "There is nothing remotely Britney- or Christina-esque about Swift." There was a fatigue with the sex-sells approach to pop music starlets, and Taylor was the antidote. "She sounds like a real teen, not some manufactured vixen-Lolita," the EW review continues. Rolling Stone put it better: "Her music mixes an almost impersonal professionalism … with confessions that are squirmingly intimate and true." The world loved Taylor because she was real; "Britney she ain't."

And boy, was she real. She had a line of sundresses at Walmart, for Pete's sake. She was just so freaking sincere. Taylor embodied the teenage experience, because she wasn't afraid to sing about it all: the best friendships, the head-over-heels crushes, and even the back-and-forth relationships with mom and dad. When Taylor was happy, you knew it. When she was pissed, you knew it. And when she'd just gotten dumped — "Heartbreak has rarely sounded as compelling."

Taylor's songs were addictively personal. When we listened to Fearless, we were listening to her life, an act of pure voyeurism. It was practically a diary set to music, or at least that's how it felt — was supposed to feel. It endeared her to her audience, and so her audience grew and grew. She was honest; we believed her. Taylor Swift peddled a kind of hyper-earnestness that was too true to ignore. Anyone who listened to Fearless became invested in Taylor Swift the person, because there was so much of her on the album that it was impossible not to. We were experiencing the act of being her right along with her. It was performance art. There was no separating the person from the songs. And that's why only now, looking back five years later, do we realize what a mistake that was.

But Would She Write a Song For You?

The trouble with Taylor's uber-personal songwriting is that it leaves her with no way to win, because what Taylor Swift sells is heartbreak. Either she can continue to write heart-wrenching songs about failed loves and bitter ex-boyfriends and have a long, successful career, or she can find happiness, settle down, and watch her career end. She can't have both career success and relationship satisfaction. No one wants to hear Taylor sing about finding the perfect guy. We want vindictive, heartbroken Taylor. If Taylor is going to keep writing hit break-up songs, she needs to keep having break-ups. That's why we know that all of Taylor's relationships are doomed to fail: because they need to. She needs the stories to write the songs to sell the records. There's a reason why the song on Fearless that blew her up to superstardom is about a fictional relationship (literary inaccuracies aside). It has to be. If it were real, Taylor's career would've been D.O.A.

Which is what makes so many of the songs on Fearless so problematic. When she sings about finding true love, we know now it doesn't happen. It's counter-productive to her career. The bridge of "White Horse" is this idea in plainest terms: "I'm gonna find someone someday who might actually treat me well," she sings. In 2008, that line was uplifting — we were rooting for Taylor. In 2013, that line sounds jaded and cynical. We know now that the someones she finds are high-profile celebs that lead to tabloid-fodder break-ups that become emotionally devastating hit songs. Taylor right now has no interest in a successful relationship. She needs the tragic ending.

And honestly, good for her. There's nothing wrong with choosing career over romantic satisfaction. It's a shame that she can't have both, but the way Taylor has crafted her career, it's impossible. The personal intimacy of her songs, and the content of those songs, means that her personal life has to remain tragic. Any song on Fearless that says otherwise is a lie.

There is, though, one lyric on Fearless that is the crux of Taylor Swift's entire career. Toward the end of "Fifteen," she comes to terms with her impending break-up:

"Back then I swore I was going to marry him someday, but I realized some bigger dreams of mine."

That, right there, is Taylor Swift in 19 words. She forgoes a happy relationship for fulfillment somewhere else. She finds satisfaction not with this boy, but with the millions of records she's going to sell using their break-up. It's one hell of a silver lining, and actually a pretty damn good message to send her listeners. They aren't defined by their romantic relationships, but rather what they do with their own lives. The line ends up being one of the most positive moments on the album, for the exact reason so many of the songs on Fearless are now depressing. In 2013, we realize Taylor made the right choice — she has had a career beyond her wildest imagination. While the much of the rest of the album is tragic five years down the line, this is a true bright spot. Taylor won on her own terms.

Let Me Finish

Nearly a year after Fearless released, Kanye West upstaged Taylor at the Video Music Awards. A more perfect pop culture moment has never happened. Is anyone better than Taylor at being wronged? It triggers some parental instinct in us. We needed to feel outraged for Taylor. It was the perfect cap to a year that saw Taylor Swift, musical artist and Taylor Swift, teenage girl merge into one Taylor Swift, superstar. The themes of her music bled into real life, and this was the culmination. Hell, of course she was going to write a song about it. There isn't so much a line between the personal and professional for Taylor Swift as there is a membrane, as parts of each diffuse from one side to the other. The VMA incident proved that. This was the Taylor Swift experience, and we were all along for the ride.

Sure, it's easy to get tired of Taylor. A lot of her "sincerity" can feel played out, overwrought, and cliché. She has a knack for making us roll our eyes. But even two albums and five years after Fearless, there's still something remarkably refreshing about the way she's not afraid to wear her heart on her sleeve. It's never hard to tell what Taylor Swift is thinking.

Listening to Fearless now isn't the same as listening to Fearless in 2008. We know things now that we didn't know then, we've seen how things played out. And maybe that's OK. Fearless is dynamic. As long as Taylor Swift is around, it'll keep meaning different things. Maybe it's not as hopeful as it once was. Maybe the songs didn't turn out the way we wanted them to. But one thing is for sure: it was, and is, worth experiencing.