Having grouped over 75 songs, recording with Nathan Chapman, who produced all but one song on Taylor Swift, commenced soon after Taylor completed touring with George Strait. At that point, she was simply trying to build off her trailblazing debut. “There was definitely an unwritten stress,” said studio engineer Chad Carlson. “We knew we could make a monster record, but we put a lot of pressure on ourselves.” In the process, Taylor made her record producing debut. She emphasized the authenticity of the songs’ emotional sentiments over technical rigidity: “I think it’s the writer in me that’s a little more obsessed with the meaning of the song than the vocal technique.” Thereon, her and Chapman recorded and cut an abundance of songs to keep the best material on the album. Thirteen tracks were intended; Taylor attributes it to be her lucky number.
Taylor continued working on Fearless throughout 2007 and 2008 in short spurts during time off between touring. By January 2008, she had recorded approximately half of the songs that would appear on the final cut of Fearless. The remainder of the songs came in the last two recording sessions: one held in March 2008, the other held sometime in the summer of 2008. Apart from newly penned songs, Taylor recorded a few that she had written for her debut album, believing there were stories that deserved to be put out:
Fearless is full of charming songs about love and heartbreak. At 18, Taylor was extraordinarily good at regarding teenage life with a kind of wistful, sepia-toned nostalgia. She wrote about her own experiences, names intact, giving her songs an almost radical intimacy, especially in a pop world known for impersonal brush-offs. “I have become much more comfortable writing about myself,” she said. But she also noted that most songs were dramatized observations of her real-life:
Fearless feels like what being a teenage girl feels like. It has the sparkling hope of a young woman thrilled to finally be stepping into adulthood, impatient to live out the romances she has grown up on, all while chiding her crushes for not noticing her. It captures the age when you are looking forward to a future outside of school and away from your small hometown. All throughout the album, Taylor maps the interior world of a girl waiting for her real life to begin, so she can get off the bleachers and discover who she’s supposed to be:
That’s the thing about being a teenager: Love is always a matter of life and death, every relationship either Sleeping Beauty and Prince Charming or Tristan and Isolde. That’s also why Fearless employs fairytale imagery throughout. Yet even at a relatively tender age, Taylor had figured out how to view her experiences – and those of her best friend Abigail and others – with an artist’s eye. Her knack for dissecting youth so honestly separated her from the pack of teenage starlets who relied on big-name producers, songwriters, and television shows for a music career. She was the rare ingenue who actually played the part (and guitar). In Taylor, the young women of 2008 found 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, Taylor came off as the real deal, with her images of boyfriends who opened car doors and cheerleaders as romantic rivals. She was 18, wide-eyed, naive, hopeful – and that’s how she sounds on Fearless.
But the new level of attention also led to the decimation of Taylor’s privacy. “Every single one of the guys that I’ve written songs about has been tracked down on MySpace by my fans,” she said, a little giddy. “I had the opportunity to be more general on this record, but I chose not to. I like to have the last word.” That would become less tenable in the future, though, as her personal life made its way into the tabloids, as it had in late 2008 in regard to her never-confirmed relationship with Joe Jonas.
All in all, Taylor Swift had suggested that its namesake had a unique talent for narrative structure and a true gift for building living characters – characters who seem real and who remind us of ourselves. Fearless not only confirmed that suggestion, but showed real growth and maturity in Taylor as a songwriter – where Taylor Swift sometimes struggles to get past the surface of its character’s emotions and conflicts, Fearless is piercingly honest and surprisingly bittersweet.
Regarding the album’s production, Taylor’s maturation on Fearless is deliberate and careful, styled after the crossover country-pop of Shania Twain and Faith Hill before they turned into divas. Despite the success of her self-titled debut, there was nothing at all diva-like about Taylor in 2008: she’s soft-spoken and considerate, a big sister instead of a big star.
There may be a hint of youthfulness to her singing but that is the only hint of girlishness here; Taylor’s writing is sharply, subtly crafted and the music is softly assured, never pushing its hooks too hard and settling into a warm bed of guitars and keyboards. Like many country-pop albums of the 2000s, the pop heavily outweighs the country – there aren’t fiddles here, there are violins – yet Fearless never feels garish, a crass attempt at a crossover success. It’s small-scale and sweetly tuneful, always seeming humble even when the power ballads build to a big close. Taylor’s gentle touch is as enduring as her songcraft. However, the album’s pop crossover appeal was much discussed by critics. Taylor, in an interview with The Philadelphia Inquirer, responded to the critical debate:
Taylor made her debut as a record producer on Fearless, co-producing all tracks with Nathan Chapman. One of their reference points for the album’s sound was the bright 2007 hit “Bubbly,” by Colbie Caillat. “There was a certain honesty and commitment to keeping the arrangements simple that that record had,” Justin Niebank, who mixed Fearless, told Billboard. “Taylor and Nathan loved the fact that on ‘Bubbly’ you could really sense that it was just an honest person sitting in a room surrounded by musicians.”
After completing the album’s first track, Taylor deeply deliberated her personal definition of the word “fearless”. She then started contemplating the word to title the album, and to assure she was making the correct decision, applied it to every song on the album. She explained the title’s meaning to The Boot:
In another interview, she added: “I have moments where I’m afraid of the music industry, I’m afraid of being average, I’m afraid of not mattering to people. I’m not afraid for this second album, honestly. There are moments when I think, ‘Is there anything that’s missing?’ But there’s really not.”
On June 8, 2008, Taylor performed some songs from
Fearless on Clear Channel’s
Stripped. The album’s first commercial release, “
Change” was made available via the iTunes Store on August 8 as a promotional single. It was included on the
AT&T Team USA Soundtrack, a compilation of songs played during the United States’ participation in the 2008 Summer Olympics. A couple of months later, a digital campaign launched through the iTunes Store, called “Countdown to
Fearless.” It featured one song released each week during the five weeks leading to the album’s release. “
Breathe” was released as a promotional single exclusively via Rhapsody on October 21, 2008.
The thirteen-track standard edition of
Fearless was finally released on November 11, 2008, by Big Machine Records. An international edition, featuring three additional tracks — “
Our Song“, “
Teardrops On My Guitar“, and “
Should’ve Said No” from Taylor’s debut record —was released on March 9, 2009, by Big Machine in partnership with
Universal Music Group.
Taylor made many television appearances to promote
Fearless throughout late 2008, performing on shows including
The Ellen DeGeneres Show (where an entire episode was dedicated to her album release party),
Good Morning America, and
Late Night with David Letterman. A special
CMT Crossroads episode featuring Taylor and rock band Def Leppard singing each other’s songs was recorded on October 6 at the Roy Acuff Theater in Nashville, and aired on CMT on November 7, 2008. Her performances at awards shows that year included the
Country Music Association Awards and the
American Music Awards. One critic wrote: “I don’t say this lightly: Swift’s ability to market both her products and herself as a brand doesn’t recall the media blitzkriegs of past teen idols like Britney Spears or New Kids on the Block so much as Madonna at her peak.”
Besides live appearances, Taylor used her MySpace account to promote to a young audience, sharing snippets of songs for streaming before they were released to radio, as she had done with her debut album. “I owe it to people from letting them in from Day 1.” Eventually, walls would have to be erected. After all, Jakks Pacific had just released a line of Taylor Swift dolls, making her even more of an abstract idol and less of a real person. She was also the face of the
l.e.i. clothing brand, carried exclusively at Walmart, one of many endorsements to come. That she was becoming less accessible was a problem that Taylor was, naturally, very attuned to:
She continued to appear on televised events through 2009, notably hosting Saturday Night Live, and performing at awards shows including the 51st Annual Grammy Awards, the CMT Music Awards, and the Country Music Association Awards. Infamously, at the 2009 MTV Video Music Awards, rapper Kanye West interrupted Taylor’s acceptance speech for winning “Best Female Video” with “You Belong With Me” — an incident known as “Kanyegate”, which prompted many internet memes and media coverage.
That year, Taylor also spent a considerable amount of time in England, Japan and Australia in hopes of facilitating Taylor Swift, the global brand, a move that few country acts had been able to pull off before her.
Five songs were released as singles from Fearless. The lead single, “Love Story”, was released on September 15, 2008. It peaked at No. 1 on the Hot Country Songs, and was the first country song to reach No. 1 on the Mainstream Top 40, a Billboard chart monitoring pop radio in the US. The single peaked at No. 4 on the US Billboard Hot 100, and at No. 2 on the UK Singles Chart. It was Taylor’s first No. 1 single in Australia. She had clearly benefited from a broad demographic appeal: The “Taylor Nation” ranged from country to indie-music fans to the Disney generation. Her impeccably crafted songs easily translated to pop radio, and Taylor was clearly taken with the notion of crossing over, even back then.
Fearless received generally positive reviews from music critics in the press. Many lauded Taylor’s songwriting craftsmanship. Reviews published in The Boston Globe, Blender, Entertainment Weekly, The Village Voice, and USA Today remarked that Fearless was an honest and vulnerable record contrasting with albums by other teenage singers, thanks to Taylor’s self-penned songs. Other reviews from AllMusic, Billboard, and The Observer deemed the lyrics mature for her age.
Some critics praised Fearless‘s crossover appeal. AllMusic‘s Stephen Thomas Erlewine and The Boston Globe‘s James Reed remarked that the album straddles the perceived boundary between country and pop; the former called it “one of the best mainstream pop albums of 2008”. In Rolling Stone, Jody Rosen hailed Taylor as a “songwriting savant with an intuitive gift for the verse-chorus-bridge architecture”. Christgau commented that the songs are effective partly because of “the musical restraint of a strain of Nashville bigpop that avoids muscle-flexing rockism”.
Fearless is the most awarded country-music album in history. It won “Album of the Year” at both the
Country Music Association Awards (CMA) and the
Academy of Country Music Awards (ACM) in 2009. It was awarded as the “Top Selling Album” by the
Canadian Country Music Association (CCMA) twice in a row, in 2009 and 2010. At the
American Music Awards of 2009,
Fearless won “Favorite Country Album” and was nominated for “Favorite Pop/Rock Album.” Its other accolades include a
Teen Choice Award for “Choice Female Album,” a
Sirus XM Indie Award for “International Album of the Year,” and a
Juno Award nomination for “International Album of the Year.”
At the
52nd Annual Grammy Awards in February 2010,
Fearless won “Album of the Year” and “Best Country Album.” The “Album of the Year” award made Taylor, then twenty years old, the youngest artist to win the award, a record she held for ten years. Taylor is only the second country-music artist to win the three highest awards for a country-music album by the ACM, the CMA, and the Grammys — after The Chicks with their 1999 album,
Fly — and the first to further win the Grammy for “Album of the Year” for the same album. “
White Horse” further won two
Grammy Awards that year: “Best Female Country Vocal Performance” and “Best Country Song.”
Fearless featured on 2008 year-end lists by the
Associated Press (7th),
Blender (32nd),
Rolling Stone (39th), and
The Village Voice’s Pazz & Jop (58th); and 2009 year-end list by
The Guardian (40th). Jon Caramanica in
The New York Times placed the album at No. 4 on his list of 2008’s best albums and called Taylor “one of pop’s finest songwriters”.
In November 2008, Taylor Swift became
Taylor Swift. The critical and commercial successes of
Fearless established her as a mainstream star beyond the country-music scene. During this album cycle, 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. Taylor’s “persona” was complete at just 18 years old.
Taylor’s songwriting on
Fearless cemented her trademark confessional narratives. In a 2019 retrospective review of the album,
Pitchfork commented that the album was a testament to her abilities of writing timeless songs, noting the album’s simplicity and earnestness. Other retrospective reviews attributed the album’s enduring popularity to songs about universal feelings—heartbreak, frustration, first love, and aspirations.
Fearless placed No. 99 on
NPR‘s 2017 list of the “150 Greatest Albums Made by Women” and No. 10 on
Rolling Stone‘s 2022 list of the “100 Greatest Country Albums of All Time.”
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.”
“From the moment ‘
Tim McGraw’ hit the channel, she began to amass an audience that traditional Nashville didn’t know or didn’t believe existed, and that is young women, specifically teens,” Brian Philips, executive vice president and general manager of
CMT (Country Music Television), told
The New York Times in 2009. “It’s as if Taylor has kind of willed herself into being.”
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