Back in November 2017, Billboard celebrated Taylor Swift’s singular pop catalog in the days leading up to the release of her sixth LP, Reputation, by asking five writers to argue for one of her first five studio albums as her best. Here, Jennifer Keishin Armstrong made the case for Fearless, Swift’s 2008 blockbuster sophomore LP.
In November 2008, Taylor Swift became Taylor Swift. She’d debuted with an excellent self-titled album two years earlier, but it was with the release of her follow-up Fearless that she crystallized the Country Princess persona that would propel her to globe-conquering superstardom during the first phase of her career.
During her Fearless peak, she solidified her image as the wavy-haired blonde who wore frosted blue eye shadow and pretty ball gowns to Hollywood events; the successful songwriter who, despite her burgeoning fame, was at heart just a suburban girl with a full diary and a lucky knack for catchy tunes. Even dating her first fellow star, Joe Jonas, and writing her first tabloid-baiting kiss-off, “Forever & Always,” didn’t taint her regular-girl image for her fans. TS 1.0 was complete at just 18 years old.
The numbers, too, show that Fearless represented Swift coming into her own: She wrote seven of the tracks by herself (without co-writers), compared with just three on her first album. She co-produced for the first time. Fearless went five singles deep. The first single, “Love Story,” became a crossover smash, selling 8 million copies and climbing to No. 4 on the Billboard Hot 100. And the LP would not only become 2009’s top seller, but also earned Taylor her first album of the year trophy at the next year’s Grammys.
If you’re into classic, country Swift, Fearless perfectly bridges the origin story of Taylor Swift and the superstar leanings of Speak Now. On Fearless, she’s still believable as a vulnerable everygirl, swinging between unrealistic romanticism and the dramatics of young love’s failings. Similarly, she balances her pop appeal and country roots. All of this came together in a perfect storm for young women of 2008, who found in Swift an authentic peer voice in a sea of Disney-driven pop stars, led by Hannah Montana-era Miley Cyrus. While Miley was pretending on TV to be a regular girl by day, pop star by evening, Swift came off as the real deal, with her images of boyfriends who open car doors and cheerleaders as romantic rivals. Fearless may not be Swift at her peak pop powers, but it is undoubtedly Swift at her Swiftiest.
The title track leads off the record, and it sets a classic Taylor scene from its first lines: a boy walking her to her car just after it’s rained, Swift wanting to ask him to dance right there, melodic guitars twinkling in the background. But there’s no doubt what the true monster of this album is — the LP’s centerpiece (and biggest Hot 100 hit, peaking at No. 2 on the chart), “You Belong With Me.” Her most unapologetically pop song at that point, this tune hooked anyone in its path. It was, for instance, both my gateway Swift song (at age 33) and a dance-around-the-living-room favorite of my friend’s three daughters, aged 3 through 5. The soft, a-little-bit-country verses gave way to a soaring pop radio chorus by way of one of the most memorable pre-chorus couplets ever: “She wears short skirts, I wear T-shirts/ She’s cheer captain and I’m on the bleachers.”
She uses those storytelling skills to tear-jerking, emotionally manipulative effect on “The Best Day,” an ode to … yes, her mom. Here, she employs her freakishly mature grasp on what hindsight can do to a person, toggling among scenes of bonding with her mother when she was 3, 5, and 13, memories full of paint sets and pumpkin patches and window-shopping to soothe hurt teenage feelings. Still 18 when she wrote it, she looks back at scenes from just five years earlier with the nostalgia, wisdom and sap of a 40-year-old. You can almost hear moms across the country encouraging their daughters to listen to “that nice Taylor Swift” as this song plays. Nobody ever accused Taylor of poor marketing.
Similarly, Swift offers sage advice to a slightly younger girl in “Fifteen,” speaking directly to her audience like the coolest, most understanding big sister. The song starts with a first day of high school, and walks us through major moments—hoping a senior boy will talk to you, meeting your best friend (“a redhead named Abigail”), your first date with a boy who has a car. Again, she offers the long view: “But in your life you’ll do things/ Greater than dating the boy on the football team.”
These subtler moments, however, were lost to many critics at the time. Fearless employs fairy-tale imagery throughout — even “The Best Day” mentions Snow White and princesses in passing — and this sparked Swift’s first run-in with well-meaning feminist critics.
That successful first single, “Love Story,” drew disproportionate attention for its retelling of a Romeo and Juliet tale with a happy ending. In it, our Swiftian narrator engages in a banjo-driven forbidden romance and plays on every possible Disney-princess fantasy: “Romeo, save me, they’re trying to tell me how to feel,” she pleads before Dad inexplicably reverses course and Romeo puts a ring on it before the end of the song. But “White Horse” erases the hope and naivete of that happy ending — and if you put any faith in album sequencing, tellingly comes two songs later. It’s pretty clear: “I’m not a princess, this ain’t a fairytale,” Swift achingly acknowledges, ultimately sighing, “It’s too late for you and your white horse to come around.”
Her songwriting specialty, the scorned-lover anthem, provides an even more bracing antidote to the fairytale-telling. In fact, she includes three love-gone-wrong songs toward the end of the album (followed only by “The Best Day” and the relatively lackluster anthem “Change”). There’s the Jonas-inspired “Forever & Always,” setting perhaps the strongest precedent for future Swift hit jobs (“Did I say something way too honest, made you run and hide/ Like a scared little boy?”) “You’re Not Sorry” states the obvious over a piano ballad melody. “Tell Me Why” cuts deeper with its upbeat-sounding fiddle riff and lines like, “Why do you have to make me feel small/ So you can feel whole inside?”
Her burns would of course grow hotter and pithier with time. But that’s part of Fearless’s charm in the Swift oeuvre: Here, she was wise, but still innocent, hopeful but not gullible, skillful but not too slick. She was just a girl with a guitar, stories to tell and only a handful of tabloid headlines to deal with.