Billboard asked five writers to argue for one of Taylor's first five studio albums as her best. Here, Jennifer Keishin Armstrong makes 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.