Why _______ Is the Best Taylor Swift Album: Taylor Swift (2006) | Speak Now (2010) | Red (2012) | 1989 (2014) | Reputation (2017)
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.”