The Fearless Era
Table of Contents
You don’t have to look further than the numbers associated with Fearless for proof of its domination. The most-awarded album in country music history and her first real pop crossover effort, it debuted at No. 1 and became the best-selling album of 2009, making Taylor, who was 18 when Fearless was released, the youngest artist in history to have that distinction. At 20, she also became the youngest-ever artist to win a Grammy for “Album of the Year”, when Fearless won the night’s top prize, along with three other trophies, at the 2010 Grammy Awards. Of its five singles, two became crossover hits, “Love Story” and “You Belong With Me,” which sold millions of copies each and firmly established her in the pop world. Before Fearless, Taylor had never headlined a tour — just months after its release, she was selling out arenas (and a stadium) on her “Fearless Tour“.
On December 11, 2017, Fearless became only the 121st album in music history to achieve a Diamond certification in the US, having sold over 10,000,000 copies in America.
“When the Fearless album came out in 2008 you could feel this tidal wave was coming. That led to the first headlining tour and our first overseas trips,” Scott Borchetta, CEO of Big Machine Records, said in 2018. “That Fearless era was the one that we were really going to do some big things.”
The Famous Girl Next Door
Clearly, Fearless wasn’t just an album for Taylor. It was an era, one that much of America likely still associates with her to some extent. Fearless is interesting because it was the first time Taylor took her major themes mainstream, as well as the last time she could present herself as the girl next door, instead of the mega-famous person she was about to become. Fearless established Taylor’s persona of the wide-eyed, guitar-toting girl with her ball gowns and flowing blonde hair, who wrote her own songs about fairytales and Shakespearean heroines and the occasional famous ex. In retrospect, it’s more than a little reductive. And while Taylor certainly participated in the princess-ing of her character during these years, revisiting the reviews of Fearless reveal just how many of the critical takes used her status as a teenager almost as a genre signifier, that she was making teen music for teen listeners, with more than one article containing some version of the line about her being broadly appealing, “though she’s a teenage girl.”
Fearless is not just an album for teenage girls, nor is it limited to being about the experiences of one. It is not, by any means, a juvenile work. Upon listening to the album, it is clear that Taylor’s skills for writing earworm melodies and spinning vivid imagery out of plainspoken storytelling are a remarkable reminder of her talents as an artist.
Capturing the Teenage Life
Taylor composed eight of the 13 songs on Fearless without a co-writer and said that the follow-up to her eponymous debut album, released two year’s previously, showed her progress as a lyricist. “I had become much more comfortable writing about myself,” she said. Taylor, who was a month shy of 19 when Fearless was released, said the songs were full of very personal details about her life, and that the main themes of the album were “boys, love and relationships”. Taylor’s ability to capture teenage life with a sort of wistful nostalgia proved immensely popular and catapulted her out of the traditional Nashville country music charts and into the pop mainstream. With Fearless, global fame truly arrived for Taylor.
Fearless feels like what being a teenage girl felt like. It has the sparkling hope of a young woman thrilled to finally be stepping into adulthood (“Fearless“, “Fifteen“), impatient to live out the romances she’s grown up on (“Love Story”), chiding her crushes for not noticing her (“Hey Stephen“, “You Belong With Me”). She’s looking forward to a future outside of school and away from her small hometown. Even amid the quiet devastation of “White Horse“, Taylor asserts that she’s “going to find someone someday who might actually treat [her] well.” She maps the interior world of a girl waiting for her real life to begin, so she can get off the bleachers and shed this awkward phase.
Five singles were issued from the album. The first, “Love Story’” shattered records for the music industry. Featuring lyrics that invoked Shakespeare’s “Romeo And Juliet”, and with an eye-catching video to accompany its release, the song was a crossover hit that sold more than eight million copies worldwide. It quickly became the best-selling country song of all time.
As well as having an assured feel for songwriting, Taylor showed she had a gift for creating melodies and countermelodies. Her verse-chorus-bridge structures were sleek and professional in lyrics unashamedly aimed at youngsters. In “Fifteen’” she sings “In your life you’ll do things greater than/Dating the boy on the football team/I didn’t know it at 15”. Her American high-school romance narratives proved to have universal appeal.
The Fearless Tour
MTV VMA Incident
Most Awarded Country Album
Fearless frayed Taylor’s reputation in a way that wouldn’t let up for years, if ever, largely because of its critical success. In 2009, she won five American Music Awards, including “Artist of the Year” and “Favorite Country Album”. Billboard named her 2009’s “Artist of the Year”. Taylor further took home four Grammys at the 2010 awards, including “Album of the Year” and “Best Country Album” for Fearless, and “White Horse” was named “Best Country Song” and “Best Female Country Vocal Performance”. Taylor was the youngest artist ever to win “Album of the Year”. She also became the youngest ever artist to be named “Entertainer of the Year” by the Country Music Association. Fearless also won the Association’s “Album of the Year” award. To this day, Fearless is the most awarded country album in history.
In 2019, Rolling Stone wrote: “In retrospect, it’s pretty incredible that an institution as stodgy as the then-Recording Academy were able to see 20-year-old Taylor for who she already was: one of the most important singer-songwriters of her generation. Following her pop crossover, Fearless tends to get overlooked a little in terms of the great leap forward it represented at the time. But it brought country into the bedrooms of teen girls who might’ve rocked out to Avril Lavigne and Michelle Branch earlier in the decade, and showcased not only the pop chops that would get bigger but the storytelling instincts that would get better — in the same smash hit songs, no less.”
Taylor made her acting debut in a 2009 episode of CBS’s CSI: Crime Scene Investigation, playing a rebellious teenager. The New York Times noted that the character allowed Taylor to be “a little bit naughty, and credibly so”.
Later that year, Taylor both hosted and performed as the musical guest for an episode of Saturday Night Live. Entertainment Weekly described her as “this season’s best Saturday Night Live host so far”, noting that she “was always up for the challenge, seemed to be having fun, and helped the rest of the cast nail the punchlines”.
In 2010, Taylor made her feature film acting debut in Valentine’s Day. The romantic comedy, released the following year, saw her play the ditzy girlfriend of a high school jock, a role in which Los Angeles Times found “serious comedic potential”.
The Definition of Fearless
In the album’s linernotes, Taylor explained why she had chosen the album title and what the word “fearless” meant to her: “Fearless is getting back up and fighting for what you want over and over again… even though every time you’ve tried before, you’ve lost,” she wrote. “It’s Fearless to have faith that someday things will change.”
Fearless will always play a special role in Taylor’s story. It was the album that made her a star, and that captured her at the point at which she most believed in magic. The joy of Fearless is how its spirit will live on — in her 2021 re-recording Fearless (Taylor’s Version), in her greatest-hits repertoire and her live shows, certainly, but also in her recordings to come, whenever she needs to channel the joys and pains of youth.