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The Fearless Era

2008-2010

Most people didn’t have an opinion about Taylor in early 2008 because even though she was popular — having sold millions of copies of her debut self-titled record — she wasn’t mainstream. She was a country star, big on country radio and winner of country awards, but if you didn’t listen to country music, you could be safely ignorant about her whole deal. It was Taylor’s second album Fearless, released on November 11, 2008, that transformed her from Taylor Swift “The Artist” into Taylor Swift “The Phenomenon.”

In other words: Fearless was the last album Taylor released before she was Taylor Swift, a famous person you were legally required to know about who would be constantly involved in incidents betraying the normalcy she purported to embody.

The Breakthrough

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

Fearless received promotion from Taylor’s first concert tour, the “Fearless Tour“, which grossed over $63 million. Taylor Swift: Journey to Fearless, a concert film, was aired on television and later released on DVD and Blu-ray. Taylor also performed as a supporting act for Keith Urban’s “Escape Together World Tour”.

MTV VMA Incident

In September 2009, the music video for “You Belong with Me” won the MTV Video Music Award for “Best Female Video”. Taylor’s acceptance speech was famously interrupted by rapper Kanye West. The incident was the subject of controversy and frequent media attention, resulting in many internet memes. President Obama even chimed in, calling West a “jackass”. James Montgomery of MTV argued that the incident and subsequent media attention turned Taylor into “a bona-fide mainstream celebrity”. To this day, it is one of the biggest pop culture moments of the century.

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.”

Non-Album Releases

Aside from Fearless, Taylor contributed backing vocals to John Mayer’s “Half of My Heart“, a single featured on his fourth album, Battle Studies (2009). She co-wrote and recorded “Best Days of Your Life” with Kellie Pickler, and co-wrote two songs for the Hannah Montana: The Movie soundtrack — “You’ll Always Find Your Way Back Home” and “Crazier“. Taylor also provided vocals for Boys Like Girls’ “Two Is Better Than One“. She contributed two songs to the Valentine’s Day soundtrack, including “Today Was A Fairytale“, which became her first No. 1 on the Canadian Hot 100 chart and reached no. 2 on the Billboard Hot 100.

Acting Debut

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.