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10 Years Later, Taylor Swift’s ‘Fearless’ Still Slaps

When it was released in 2008, Swift’s sophomore album launched a thousand takes. Today, it’s best remembered as a simple time capsule

Taylor Swift "Fearless Tour" 2009

Taylor Swift during the "Fearless" tour at Madison Square Garden on August 27, 2009 in New York City.

Theo Wargo/WireImage for New York Post

Like Propel water, The Scarlet Letter and mechanical pencils, Taylor Swift’s Fearless pairs well with the sporadic squeak of team-issued sneakers, overpriced hot lunches and the kind of angst that defines comfortably suburb-bound teenage years. Sliding open the album on Spotify with my iPhone 8, I can still feel my limbs stretched in all directions, hear the snap-crackle-pop of a dozen adolescent girls’ joints going through the motions of yet another warm-up to what would become the soundtrack of my high school varsity dance team’s inner and outer lives, as well as leave poptimism forever changed.

I am 27 now, still anxious but inflexible, no longer clinging (as) tightly to singular albums to tell the emotional landscape of my life — but back then, Fearless was god. Swift was barely into legal teenagedom when compiling her sophomore album’s original 13 tracks, but more than the happenstance near-synonymy of our ages (I’m younger by 1 year, 6 months, 27 days), the four-walled, high school claustrophobia induced by the album is a matter of skilled musical mood setting. From the first downbeat of the inaugural title track to the last flippantly rebellious “hallelujah” on “Change,” Swift traps us in the mind of an ungainly teen as she was once trapped, as I was, as so many others wading the ambiguity between comportment and desire that doesn’t quite end when gowns come on and caps fly up.

Like so many notebook pages on the golden screen, Fearless is filled with boys. Stans and haters have their theories, but I like to think of each song as an archetype, less true stories of relationships gone sour than a young woman’s true to life hetero-ethnography. There are the boys who do good — the “Fearless,” “Love Story,” “Hey Stephen,” “The Best Day” boys (the last a tribute to Dad) — the boys who nurture and love intensely. They do all the usual country boy things, all the usual cinematic things: driving slow, kissing in the rain, flouting archaic inter-familial squabbles. They honor their promises and, most of all, leave the narrator better changed for her affection.

These boys who do good are short-lived. By Track 2, “Fifteen,” we’re already checking in to Heartbreak Hotel for the upteenth time with an account of that age generic enough to warrant a fan-made montage of clips from Degrassi: The Next Generation. The song tells an allegedly universal story of freshman year woes, complete with riding in cars with senior boys who also play football (because of course). It’s saccharine, sung in the vernacular of normative coupling that would become Swift’s enemy in the gossip pages. But the limited lexicon is not necessarily untruthful. “Fifteen” has aged about as well as anyone would expect, but some of those refrains make me yearn for arms long enough to slap all the powers that be responsible for belittling the whims of young girls. And according to the greater duration of Fearless — tracks like “White Horse,” “Breathe,” “Tell Me Why,” “You’re Not Sorry,” “The Way I Loved You,” and “Forever & Always” — the greatest threat to the happiness of teen girls are boys.

November 2008 looks rosy from here. America had just elected its first black president, the man who promised too much hope and change to possibly be true, but faith felt good back then. Men had committed just five mass shootings over the past year with one more on the way in December (2018 has 307 mass shootings to its name so far). The nation boasted just under 150 recognized active white supremacist groups (that number would climb to over 1,000 during Obama’s presidency). Global finance was in crisis but cable networks were still winning Emmys. Amy Winehouse was alive. Kanye still made sense and a bright-eyed, hair-tousled new country darling was exclusively concerned with dating, rather than local politics.

Like any celebrity who is also a woman, but also in a lane quite her own, Swift’s relation to mainstream feminism wanes and waxes with the season. A female artist beloved by the girls for whom her songs are written, Swift and her music are therefore more scrutinized, more rigorously excavated for signs of harmful messaging than her male singer-songwriter peers. Fearless frayed Swift’s reputation in a way that wouldn’t let up for years, if ever, largely because of its critical success. Swift took home four Grammys at the 2010 awards, including Album of the Year, beating the Dave Matthews Band’s Big Whiskey and the GrooGrux King, The Black Eyed Peas’ The E.N.D., Beyoncé’s I Am… Sasha Fierce and, most egregiously, Lady Gaga’s debut studio album, The Fame. The perceived slight invited robust inquiry into this supposed album of the year, and the aesthetic discrepancy between the two quickly turned to politics.

Autostraddle’s Riese called Swift “a feminist’s nightmare,” the enemy of “brave, creative, inventive, envelope-pushing little monsters” everywhere. An accompanying infographic, “a symbolic analysis” of Swift’s works to date, cataloged her most damning motifs, including “virginal” imagery, “the stars,” “crying,” and the 2AM hour. At Jezebel, Dodai Stewart agreed that Gaga was the rightful winner, speculating that in a race between “Gaga the liberal versus Taylor the conservative,” the latter “makes the Academy feel more comfortable.” One joy of pop culture is the revelation of how melodramatically things can change. Last month, Swift announced her endorsement of Tennessee Democrats Phil Bredesen and Jim Cooper for the midterm elections; meanwhile, Lady Gaga hews the path of glamorous respectability on her lengthy A Star Is Born Oscar campaign.

Feminist readings of Fearless weren’t wrong, exactly. Allies on the album come in strictly male form, while other girls are competition for Swift’s persecuted first person. Even the red-headed bestie Abigail becomes a lesson in chastity, losing her virginity — “everything”! —to the boy who broke her heart (the foil to Swift’s main character, whose dreams of living in a big ole city protect her from such a fate). The charting single “You Belong With Me” is a bouncy jaunt through the valley of me versus those other girls. The video that won Best Female Video at the MTV Video Music Awards over Beyoncé’s “Single Ladies” — to seismic effect — stars Swift as both the frizzy blonde, bespectacled weirdo in band and the sleek brunette cheerleader with the man (Lucas Till who now plays MacGyver on CBS). In true romantic comedy fashion, Good Swift, clothed in white, ends up with the guy in the end, defeating Bad Swift, whose only crimes it seems are great taste in footwear and not appreciating her high school boyfriend’s likely moronic sense of humor. Both the song and video became emblematic of a kind of Swiftian all-for-one girl power. Her 2017 video for “Look What You Made Me Do” resurrects and buries all sorts of Swiftisms, including the iconography of the uncool girl who features so heavily in the Fearless-era of her oeuvre.

Pop music exists not to elevate our souls or our politics, but to safely wade in the muck of our pettiest appetites, whether they come with trap drums or in serenades. Pop music deserves interrogation, but it will never exceed us. Fearless was a diary, sounding like the selfishness that bubbles up regardless of one’s intellectual or political guards against it.  The debate it ignited wouldn’t happen were it released today, amidst all this. It’s a relic of a time when determining exactly what an album meant, culturally and aesthetically, was a crucial discussion to have in public, when nuance had stakes. Compared to the basic moral tenets we now expend so much of our energy defending, such communal acts of criticism feel small and regretfully scarce. Fearless was a moment, now relegated to a time capsule, no longer a prompt.  

In This Article: Taylor Swift

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