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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 and who would be constantly involved in incidents betraying the normalcy she purported to embody.
Table of Contents

Living With Her Family

In 2008, Taylor still lived at home with her parents in Hendersonville, a suburb outside of Nashville, in a big house overlooking Old Hickory Lake. “In the summer, people fish off the dock. More people now. Apparently, there are more fish now,” Taylor commented, when asked about the lack of privacy at the lake shore. The family was wealthy before she became a star — both of Taylor’s parents have had careers in finance, which made them particularly good advisers, and they weren’t interested in their daughter’s fortune. Her mom, Andrea, usually travelled with Taylor at the time, and her father, Scott, a kind and friendly stockbroker, stayed at home with her younger brother Austin, a 16-year-old lacrosse player and academic overachiever.

The mantle of the Swift’s living room was crammed with bulky glass awards, and posters of Taylor lined the hallways; a large sitting room was devoted to racks of clothes that she had worn during performances or in public, with a sign affixed that read, “Please go through: Keep or give to Goodwill.” Austin had moved into a room on the garage level, but Taylor still lived in her childhood bedroom. It was a small room, decorated almost exclusively in pink and purple. Any sign of her life as a superstar had been scrubbed, with the exception of a postcard from Reba McEntire. Living in Nashville, Taylor said, offered its own protective layer. “Keith and Nicole live there. Tim and Faith live there. We can all go to the grocery store in our sweatpants because the paparazzi have no idea Nashville exists.”

Headfirst, Fearless

“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.”

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 Taylor’s 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”.

The Girl Next Door

At 19 years old, Taylor was always on good behavior, intent to be a good role model for her legions of young fans. Not for nothing, she had been tagged the “anti-Britney.” In high school, she had a 4.0 average; when she was home-schooled during her junior and senior years, she finished both years of course work in 12 months. She wouldn’t engage in any remotely dangerous type of physical activity and bit her nails to the quick. She said she had never had a cigarette, and had never tried a drop of alcohol. “I have no interest in drinking. I always want to be responsible for the things I say and do. Also, I would have a problem lying to my parents about that,” she said.

In the media, along with the Jonas Brothers and a gaggle of young Disney stars like her pals Miley Cyrus, Selena Gomez and Demi Lovato, she was part of a backlash against the “scandalous” TMZ culture of earlier in the 2000s decade. Taylor admitted in an interview with Rolling Stone in 2009 that she was fascinated by girls like Paris Hilton when she was younger but said that she never thought the gossip about these women was true. “You should never judge a person until you know the full story.” Her then label president told a magazine at the time, “Taylor’s the perfect person for this media moment. She really is the girl next door. She hasn’t been drunk at a party, hasn’t been in any crazy photographs. In this moment of total madness in the culture, Taylor’s fans know they can count on her. I think parents just go, ‘Oh, thank God my kids love Taylor Swift.’”

Taylor took her position as a role model seriously. One of her biggest fears involved “me making a bunch of bad decisions and embarking on a painful, slow, devastating tailspin.” She’d discovered VH1’s Behind the Music and E! True Hollywood Story as a child and remained a diligent student of the genre. “Like, if I go to a bar, even if I’m not drinking, who’s to say that a source isn’t going to say that I was doing something I shouldn’t have been doing? So, it’s not only about your own moral compass, but the moral compasses of other people that you don’t know. I overthink everything. I overanalyze everything.”

Self-preservation was one of Taylor’s favorite phrases, and she used it in reference to both her professional and personal lives. From the beginning, she wanted to have a long career, not get tossed away like most teen stars. She was certain she would never let herself get caught up in any shenanigans. “When you lose someone’s trust, it’s lost, and there are a lot of people out there who are counting on me right now.” TV talk show hosts loved Taylor because she possessed such a rare collection of traits. With her cover girl beauty and effervescent personality, she was great on camera, and she brought with her a suitcase full of songs that weren’t ashamed to voice the perspective of a living, breathing and sometimes heartbroken teenager. Regarding her songwriting, she said:

«I usually generalize it and say I like to write songs about boys, but it’s more than that. I like to write songs about relationships, and the steps that take us to a heartbreak, or the steps that take us to falling in love and all that’s in between. It’s my favorite thing to write about [because] you never run out of material, and you keep coming back to it. It’s like moths to the flame, no matter how many times you’re hurt by love, no matter how many times you’ve gotten your heart broken, you’ll always come back, no matter how long it takes. It could be years, but you will be attracted to love again.»

Taylor Swift

Capturing the Teenage Life

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. During the Fearless era, Taylor established her 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.

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. As a whole, the album represented a major advance in Taylor’s confidence and acumen as a songwriter and evinced complete faith in her conversational vocal style, one that positioned her as the celebrity teen that other girls would most like to hang out with and the one most boys would want to ask to the prom.

That was still something with which Taylor struggled. For most of her time in high school, she and her best friend Abigail thought of themselves as ugly ducklings. “We kind of came to the conclusion in ninth grade that we were never going to be popular, so we should just stick together and have fun and not take ourselves too seriously. That’s why I had so much fun in high school, because I didn’t focus too much on the fact that I wasn’t really in the clique.” Many of her songs on her first two albums are not about her own personal experiences with love — about half were inspired by her friends’ relationships:

«I’m fascinated by love rather than the principle of, ‘Oh, does this guy like me?' I love love. I love studying it and watching it. I love thinking about how we treat each other, and the crazy way that one person can feel one thing and another can feel totally different. It just doesn’t take much for me to be inspired to write a song about a person, but I’m much more likely to write that song than do anything about it. You know, self-preservation.»

Taylor Swift
As a teenager, love is always a matter of life and death, every relationship either Sleeping Beauty and Prince Charming or Tristan and Isolde. Yet even at a relatively tender age, Taylor had figured out how to view her experiences with an artist’s eye: “I think as a songwriter you need to have a completely wild imagination about what could be and what might have been. Some of your most heartbreaking material is what could have been, and some of your most romantic material is what could be.”

The Fearless Tour

Before Fearless, Taylor had never headlined a tour — just months after its release, she was planning the “Fearless Tour“. In early 2009, she started rehearsals at a studio on the outskirts of Nashville for her first arena (and one stadium) tour of 52 cities, set for launch in April. One date at the Staples Center in Los Angeles sold out in two minutes, New York’s Madison Square Garden only took 60 seconds. A couple of months later, she was used to the hectic schedule of being the headliner of a nationwide touring spectacle. She told Glamour in June 2009:

«On any given day I do five or six different interviews. If we are somewhere really pretty, I'll try to experience the place I'm in. My meet and greet schedule starts at 5:00 P.M. The show starts at 8:00 P.M. Then, I'll do a mass meet and greet with people who won a radio contest, or who we found in the nosebleed section. I get really restless when I haven't worked for a day and a half. I have a recurring dream that people are lined up next to my bed, waiting for autographs and taking pictures of me!»

Taylor Swift
Overall, the “Fearless Tour” grossed over $63 million. Taylor Swift: Journey to Fearless, a concert film that captured the majority of the show, was aired on television and later released on DVD and Blu-ray.

Becoming a Brand

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. Country and pop fans alike embraced her music, but she never failed to display her country roots — always wearing a cute sundress and cowboy boots, her wrists ringed with bracelets made and sent to her by various fans. Her fashion sense was also translating into a line of inexpensive sundresses that were sold at Walmart stores. “I always thought if I ever were to do a fashion line, I wouldn’t want to do [clothes] that girls like me and girls my age couldn’t afford.”

It was one more expression of her powerful Everygirl connection with her audience, which she’d strengthened with practically a daily presence on her MySpace page: “Blogging has been really fun because I like to let people into my life as much as possible. Obviously. I think it’s important for the people who keep you going and support you and have your back out there in the world to know that you’re thinking of them all the time. I get tired. A lot. But I would so much rather be hopping from a plane to a tour bus to go on a stage to doing an interview to doing a talk show to doing this performance to doing that performance to doing an awards show. So when I start to get really physically worn down, I just mentally go back to the place when I would have to get up really early for a test in high school, and I’m like, ‘Hey, this is pretty cool.’”

MTV VMA Incident

Then came the MTV Video Music Awards (VMAs) in September 2009. Taylor had just taken to the stage to accept the award for “Best Female Video.” Here was a wholesome heroine to America’s adolescent girls, well on her way to becoming the biggest-selling digital artist in history. But rapper Kanye West, self-appointed oracle of all that is really dope, wasn’t happy. As a wide-eyed and thrilled Taylor attempted to give her thanks, West grabbed a microphone and told the assembled luminaries and viewing millions that Beyoncé was more deserving of the award. Taylor gaped. The crowd booed. Sitting down the front, Beyoncé looked mortified. West strode off into another notorious night. The incident was the subject of controversy and frequent media attention for weeks, resulting in a massive backlash for West and Taylor being pressured into making a public statement — she refused. At some point, even President Obama even chimed in, calling West a “jackass”. The incident would follow both artists for more than a decade. To this day, it is one of the biggest pop culture moments of the century.

Acting Debut

After the unprecedented media coverage, Taylor was in no hurry to redesign her career path. But she still made her first forays into acting, appearing on an episode of CSI: Crime Scene Investigation, earning positive reviews for her monologue and skits as a guest host on Saturday Night Live and making her movie debut in Valentine’s Day. Those experiences were appealing, but not enough to knock her off her current course.

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” and 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.

The Breakthrough

At barely 19, Taylor was set to be a worldwide star. She appeared at the Brit Awards in February 2009 and UK radio was already playing “Love Story.” Her 2006 self-titled debut album went triple platinum. Fearless moved 2.1 million copies in less than two months and in 2009, Taylor sold more albums than any other artist. In other words, she’d beat out Britney, Beyoncé, Lil Wayne and Coldplay. She was unlike any country star before her, her mainstream pop aesthetic attracting a devoted young audience in what was traditionally a middle-aged market. She told Teen Vogue in March 2009:

«All of this is amazing, but it doesn't guarantee anything about the future. I still haven't made it to where I want to be.»

Taylor Swift
But fame and success made everyday life for Taylor more difficult too. She told Glamour in June 2009: “Sometimes I don’t get invited to things because my friends know it’s going to be a hassle to take me. I’ll find out that a group of my friends went out to dinner, but they wanted it to be a low-key night and not worry about people coming up to the table every other second and asking for autographs, so they didn’t invite me. I can understand that.” So, despite her success, Taylor still wanted to be the girl next door.

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”. She was the youngest artist ever to win “Album of the Year” and also became the youngest ever artist to be named “Entertainer of the Year” by the Country Music Association. Fearless further won the Association’s “Album of the Year” award. To this day, Fearless is the most awarded country album in history. “I will never forget this moment, because in this moment everything that I have ever wanted has just happened to me. This has been the most magical night,” Taylor said through tears at the CMAs during her “Entertainer of the Year” acceptance speech.

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.”

The Definition of Fearless

In the album linernotes for Fearless, 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.”

The Fearless era 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.

The album and its success also foreshadowed what was to come: Though Taylor had been embraced by the country greats, many tracks on Fearless could be characterized as soft rock or pop. Nonetheless, “she’s not going to be chasing pop music. Pop music is chasing her,” her label wrote in a statement. Next on the agenda: Writing and launching a new album in October 2010. Moving out. And when time allowed, Taylor would hang out with Abigail.
General Information
Associated AlbumFearless
Beginning of EraAugust 2008
End of Era
TourFearless Tour
Aesthetic13
Hand hearts
High school
Romance
Whimsy
StyleSchoolgirl
Bracelets
Sequins
Ball gowns
Soft curls
ERA CHRONOLOGY
Taylor Swift Era (2006-2008)Fearless Era (2008-2010)Speak Now Era (2010-2012)
Commercial
Fearless Era

Fearless (2008)

Fearless
(Taylor's Version)

Fearless Songs

Fearless Tour

Journey to Fearless

Taylor's Discography