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FEARLESS,
THEN & NOW

When 19-year-old Taylor Swift released Fearless in 2008, it was her play to become a full-on superstar. Selling almost 600k copies in its first week en route to becoming the biggest-selling album of 2009, the 13-song collection was an accurate core sample of a 21st-century teenage girl’s heart.

Written by Swift, Fearless would win Album of the Year at the Grammys, as well as the Country Music Association and Academy of Country Music awards. Its author created a lane for the awkward, the outsider and the one pining for someone who just sees “a friend”; crossover hits “Love Story,” “White Horse” and “You Belong With Me” ultimately delivered diamond certification to the coltish songstress.

The rise of Fearless saw the exponentiation of Swift's fame. Her MTV Female Video Award win for “You Belong With Me”—over Beyoncé—caused Kanye West to charge the podium, while a romance with Joe Jonas that went sideways fueled whispers about whom these songs were about. Swift wasn’t talking, only writing. The intrigue fueled Rolling Stone, Vogue and Vanity Fair covers, the sort of curiosity reserved for pop music’s most compelling stars.

Impressive. Especially for a country artist.

Thirteen years later, this work of a young woman is many things.

For Scooter Braun and Scott Borchetta, Swift’s entire Big Machine catalog served as a meaningful asset in the sale of Big Machine Label Group to the Ithaca Group, later parceled off to Shamrock Holdings. Swift's sales numbers are daunting, the mark of these songs on generations of young people enduring.

Beyond a mere asset, Fearless’ songs are the trials, tribulations, disappointments, agonies and exhilarations that can only be experienced by a 13-, 16-, 17-year old. The innocence of “Fifteen,” “Hey Stephen” and “The Best Day Ever” were lived, not conjured. For the now-31-year-old, these songs were her awkward years, not “product” to be sold off like a commodity future.

But how does a grown woman reclaim her catalog? Taylor’s Version, designed to best Fearless’ new owners, has to serve those fans whose lives and memories are entangled with her songs. More than petulance, a sleekness to the cheery re-enactments emerges from leaning on her live band, who’ve brought these songs to life on tour for the last dozen years. Both fluid and strong, it’s lived-in, celebratory, like a summer weekend when your best friends all converge from across the nation.

Having grown as a vocalist, she brings a coquettish quality to the songs we know. She can’t retain the rawness of in-the-moment emotion, but she understands the irritation of “You’re Not Sorry,” the done-with-it of “White Horse,” the fluttering rush of “Love Story” as both an adult who survived and the girl who quivered with those outsized emotions.

Suddenly, Swift is both the mother exulting in the carpool alongside the kids living it. She’s the assured LGBTQ ally who knows the hidden crushes and the shy kid who can’t say “I love you.” Her dynamic invests a vast empowerment in songs that could be a bit too twee now yet come to life as a deeper sort of anthem here.

For fans of parsing minutiae, the debates about whether the original is better than Taylor’s Version can provide hours of fun. Beyond the six additional Platinum songs, Swift raids the vaults for six songs that could’ve made the original package. They’re probably good for Easter-egging over which song is about what, whom and why.

What’s most interesting is sonic: the power-pop sheen these unearthed songs are bathed in. As the album that transitioned her to pop radio and pop-culture consciousness, they arrive as a fuller realization of her ambition.

Dueting with Keith Urban and Maren Morris, as well as getting production help from Jack Antonoff and Aaron Dessner, along with an Elvira remix of “Love Story,” she more fully realizes Taylor 2008. This is who she might’ve been had she been a little older when fame first arrived.

With her ability to create earworm melodies and weave small details that nail the horrors of first loves (the cascading agony of “Mr. Perfectly Fine,” the cello-swathed disappointment of “We Were Happy”), Swift ramped up the production on these unearthed songs. “That’s When,” a true duet with former tourmate Urban, offers that consummate break-up/make-up moment, while the stiff-upper-lip of “Don’t You” weightlessly confesses that love doesn’t conveniently die when one person’s done.

On Fearless (Taylor’s Version), Swift establishes that she can still throw those punches, still land a jab; those songs come with a delicious thwack. But older, wiser, more resolved, the album also shows a woman mocked by many and humiliated by the tabs who turned it all into songs. Thirteen years later, she is comfortable and knowing, providing a lifeline for every kid going through it and a witness for everyone further down the road who’s trying to believe that their broken heart is all just part of being fearless.

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