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Taylor Swift Era

2006-2008

Taylor started her career as an unlikely country contender, defying industry wisdom about what would sell. By the time she arrived on the Nashville scene in the mid 2000s, the pop-country divas who’d been dominant throughout the ’90s had largely receded from view, and those programming the radio format had it in their heads that their core demographic of grown women preferred to hear grown male singers. The country-music business didn’t yet see the point in courting younger listeners, major labels had a lock on radio airplay, and Nashville’s old-school division of creative labor, which defined “singer” and “songwriter” as two separate jobs, was still the rule. But Taylor’s debut would go on to transform the genre.
Taylor may have only been 16 when she released her first single, but she quickly established herself as one of country music’s brightest, young stars of the decade. Propelled by the success of her breakthrough single “Tim McGraw,” Taylor’s self-titled debut album Taylor Swift sold millions of copies just months after its release. In addition, music industry pros and fans alike learned that Taylor was not just a singer, but a skilled songwriter who wrote or co-wrote every single song on her album.
Table of Contents

Leaving Pennsylvania

Taylor was born on December 13, 1989, in Reading, Pennsylvania. Her father, Scott Kingsley Swift, was a financial advisor, and her mother, Andrea Gardner Swift (née Finlay), was a homemaker who worked previously as a mutual fund marketing executive. Taylor also has a younger brother named Austin. Her parents intentionally raised their kids in the country, on a Christmas tree farm with a grape arbor and seven horses, while Taylor’s father commuted to work. “I had the most magical childhood, running free and going anywhere I wanted to in my head.” But her parents also prized success in the real world: They even gave her an androgynous name, on the assumption that she would later climb the corporate ladder. “My mom thought it was cool that if you got a business card that said ‘Taylor’ you wouldn’t know if it was a guy or a girl. She wanted me to be a business person in a business world.” Taylor rode horses competitively as a child, but her main hobby was making up fairy tales and singing the songs from Disney movies by heart. At six, she discovered a LeAnn Rimes record, which she began to listen to compulsively. “All I wanted to hear from then on was country. I loved the amazing female country artists of the Nineties — Faith, Shania, the Dixie Chicks — each with an incredible sound and standing for incredible things.”

At the age of nine, she then became interested in musical theater and regularly traveled to New York City for vocal and acting lessons. She spent her weekends performing at local festivals and events. But it was only after watching a documentary about Faith Hill when Taylor felt sure that she needed to go to Nashville, Tennessee, to pursue a career in country music. At the age of eleven, she first traveled to music city with her mom to visit record labels. There, she submitted a demo tape of Dolly Parton and Dixie Chicks karaoke covers, introducing herself saying: “Hey, I’m Taylor! I’m eleven, I want a record deal. Call me.” Nothing happened. But rather than discouraging her, that rejection was like rocket fuel:

«I think that was the trip that made me realize that I needed to be different. So I went back to Pennsylvania where I grew up and started writing songs. And I picked up a twelve-string guitar and started to play. That’s when I started writing every single day after school. I would write until 9pm and then do my homework. And that’s what I did for about two and a half years straight.»

Taylor Swift
When Taylor was about 12 years old, computer repairman and local musician Ronnie Cremer taught her how to play guitar and helped with her first efforts as a songwriter, leading to her writing her first song, called “Lucky You.” In 2003, Taylor and her parents started working with New York-based music manager Dan Dymtrow. With his help, she modelled for Abercrombie & Fitch as part of their “Rising Stars” campaign, had her original song “The Outside” included on a Maybelline compilation CD, and attended meetings with major record labels. After performing original songs at an RCA Records showcase, Taylor was eventually given an artist development deal and began making frequent trips to Nashville with her mother.

To help Taylor break into country music, her father transferred to the Nashville office of Merrill Lynch when she was 14, the family relocated to a lakefront house in Hendersonville, Tennessee, and Taylor started attending the public high school in town.

After School Songwriter

At high school in Hendersonville, Taylor’s interest in country music was considered normal, in contrast to Wyomissing where she’d been bullied because of it: “My friends are extremely supportive. I hang out with them as much as possible. When I’m not working, I’m with them. They know all the words to my songs. They really just support me as a person and as an artist. They’re all just beautiful to me and I love them.” Taylor was only fourteen when she was signed by the Sony/ATV Tree Publishing house. She’s the youngest songwriter to ever be hired by the music industry giant. She showed up to co-writing appointments with seasoned Music Row pros such as Troy Verges, Brett Beavers, Brett James, Mac McAnally, and The Warren Brothers expecting to be underestimated, then persuaded them of her seriousness by presenting a dozen song ideas prepared in advance. She eventually formed a lasting working relationship with Liz Rose. They began meeting for two-hour writing sessions every Tuesday afternoon after school:

«I am sixteen years old and I’m a sophomore at Hendersonville high school. I actually have high school experiences. I have a double life. During the day I walk around, talk to people, go to class, study for tests, and have crushes on boys, and then after school I go downtown to Music Row in Nashville and I write songs about those experiences. It’s really interesting because I have to explain to different writers that I co-write with, ‘Well, I can’t write at 10 o’clock because I get out of school at 3.’»

Taylor Swift
Rose thought that the sessions were some of the easiest she’d ever done. “Basically, I was just her editor. She’d write about what happened in school that day. She had such a clear vision of what she was trying to say. And she’d come in with the most incredible hooks”. Taylor told The New York Times in 2008: “I knew every writer I wrote with was pretty much going to think, ‘I’m going to write a song for a 14-year-old today. So I would come into each meeting with 5 to 10 ideas that were solid. I wanted them to look at me as a person they were writing with, not a little kid.”

Signing With Big Machine Records

Taylor also had her development deal with RCA Records, which meant that the label was giving Taylor recording time and money to record, but not promising that they’d put an album out. In some circumstances, labels can also shelve an artist. After a year of development, RCA told Taylor and her family that they wanted to keep her in development until she was 18. So she decided that she wanted to look around for other opportunites and walked away from the deal. She told EW in 2007: “It’s not a really popular thing to do in Nashville, to walk away from a major record deal. But that’s what I did, because I wanted to find some place that would really put a lot of time and care into this.” Taylor also stated that she didn’t feel like RCA wanted her to sing her own songs:

«I didn’t want to just be another girl singer. I wanted there to be something that set me apart. And I knew that had to be my writing. Also, it was a big, big record label with big superstars, and I felt like I needed my own direction and the kind of attention that a little label will give you. I just did not want it to happen with the method of, 'Let’s throw this up against the wall and see if it sticks, and if it doesn’t, we’ll just walk away.' I wanted a record label that needed me, that absolutely was counting on me to succeed. I love that pressure.»

Taylor Swift
Taylor received interest from multiple major labels but held out for Scott Borchetta, a DreamWorks Records executive. At an industry showcase at Nashville’s famous Bluebird Café in 2005, she caught his attention just as he was preparing to form his own independent record label, Big Machine Records. She became one of the first signings, and her father purchased a three percent stake in the fledgling company at an estimated cost of $120,000. Borchetta said, “Taylor and I made an aggressive deal on the back end. I’ve written her some very big checks.” Taylor began working on her eponymous debut album shortly after signing the record deal and persuaded Big Machine to hire her demo producer Nathan Chapman, with whom she felt she had the right “chemistry.” In a 2006 documentary for GAC Shortcuts, she said:

«The best part about getting a record deal was that it wasn’t just a record deal. It was the right deal for me. I’m just so grateful that I got the right one and that I’m with people that I believe in, and that they believe in me. This is my chance. This is my chance to bring my music out of my bedroom where I’m writing it.»

Taylor Swift
Taylor wrote three of the album’s songs alone, and co-wrote the remaining eight with writers Liz Rose, Robert Ellis Orrall, Brian Maher, and Angelo Petraglia. She completed the recording sessions when she was finishing up her freshman year of high school. Big Machine Records was still in its infancy on the release of the lead single, “Tim McGraw”, in June 2006. “They only had ten employees at the record label to start out with, so when they were releasing my first single, my mom and I came in to help stuff the CD singles into envelopes to send to radio. We sat out on the floor and did it because there wasn’t furniture at the label yet.”
Taylor Swift by Taylor Swift (Big Machine Records, 2006)

Taylor Swift

Taylor Swift October 24, 2006 Taylor Swift is Taylor’s debut studio album, released by Big Machine Records on October 24, 2006. She was 16 years old at the time and wrote its songs mostly during her freshman year of high school. The album was produced by Nathan Chapman, who had previously worked with Taylor on her demo recordings.

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Homeschooling

At this point, Taylor transitioned from Hendersonville High School to homeschooling at the Aaron Academy in order to focus on her music. The Swifts knew that Taylor’s schedule was getting more and more demanding every day. Whenever she and Andrea were sitting in an airport, Taylor would pull out her workbooks:

«I literally went to high school up to the point where my single was released. Over the summer, I made the decision to go to homeschooling because it comes to a point where you have to say, ‘Okay, I like school. But I love this and I can’t miss it.’ It’s hard because you have a group of friends and they’re all doing different things. They’re all talking about stuff that I’ve kind of missed out on during the week.»

Taylor Swift
Taylor was on a homeschooling program which allowerd her to do all the work herself. She would read a chapter and then do some work: “It’s really perfect for me because I can do it on planes, and I can do it on the bus. I’m trying to do as much work as I can possibly do. I wanna get through school, I really do. I wanna graduate. I just wanna do it really fast.”

With little spare time that fall, she went to the mall with a friend one day, but that was a rarity. She also managed to get to a high school football game in September at her old school, but missed homecoming because of career commitments. Likewise, she didn’t go to parties with teenage friends anymore. But she was a straight A student and got her high school diploma one year early.

Country Music From a Teenage Girl

Taylor’s debut album, Taylor Swift, was finally released on October 24, 2006. On paper, she seemed poorly positioned to carve out a place for herself in the thoroughly adult world of country music. But she wanted to prove that a young, female perspective could carry emotional weight in country music. She spent much of the year on the road with her mom, promoting the album with a six-month radio tour and numerous television appearances. Once she had her debut collection of 11 songs to discuss, she was fond of pointing out that she’d dreamed one up in math class (“Tim McGraw”) and written another for a school talent show (“Our Song”): In her GAC Shortcuts documentary, she said:

«People around here say, ‘Once you get the record deal, that’s when the hard work starts.’ And I’m well aware of that and ready to step up to that. Radio tour is when you go out and meet with every single radio station in the country. I don’t think you could do it, if you weren’t a people person. Most of the people in radio are really about music. And I love going out and talking with people who are as passionate about music as I am.»

Taylor Swift
A lot of Taylor’s fans also discovered her on MySpace, where she famously did her own posting and personally answered messages. Country artists had long been known for their accessibility, but she took the impulse further, projecting something more like friendship. The fact that she’d amassed so many online followers helped persuade country-radio programmers to play her songs; not only did she pledge fealty to the format, she was on to something way too big and important for them to ignore:

«MySpace is an awesome new thing. It’s an online website where people can really connect with artists. Every night, I really try to keep tabs on my MySpace and see people who are leaving me comments. Typically, I get about six hundred emails a day. I read all the guest book entries, I want to be a part of these people’s lives. I think it’s important to keep that personal contact. That’s the most fun thing to me, to hear what people think. And all their different stories of a first time they heard a song and how it affected them. I just love all that, I’m so consumed by it. All these people are doing this because they’re touched by the music and I could never ask for more than that.»

Taylor Swift

First Touring Experiences

Her online popularity also landed Taylor several touring gigs. She promoted her debut album extensively as the opening act for country music’s biggest artists, including Tim McGraw, Faith Hill, George Strait, Keith Urban and Rascal Flatts. Other kids her age were sitting in the audience at country shows, while she was on stage singing for more than 10,000 people every other night. But Taylor wasn’t intimidated: “Not by any measure. I’m intimidated by the fear of being average.” In her 2010 documentary Journey to Fearless, Taylor said:

«I was opening up for every single country headliner imaginable. I was opening up for Brad Paisley, George Strait, Kenny Chesney, Tim McGraw. Like, all these people that I'd always wanted to open up shows for. I was a nervous wreck. I rehearsed non-stop, over and over again. And I loved it. Those were some of my favorite times.»

Taylor Swift
At the same time, she was dreaming of one day headlining her own concert tour. In 2006, she said: “My big dream is to look out into a crowd of thousands of people and have them singing the words to my songs. That, to me, would just be everything I’ve ever hoped for.”

A Place In This World

In 2008, Taylor started playing her own sold-out headlining shows, in theaters with a capacity of around 3,000 people. Before every show, she would pose for photos for an hour at a meet-and-greet full of fan-club and radio-contest winners. And at most of the hundreds of shows she’d played so far, she stayed afterward to sign autographs till the last fan was gone, which might last anywhere from two-and-a-half to four hours:

«After a show, I try to meet and greet with as much people as I possibly can. That’s always been really important to me. Because I’ve been that kid, standing in the autograph line with my mom. I try no to refer to people who listen to my music as fans because I try to refer to them all as my friends. I’m gonna try to be a part of their lives just as much as they’re being a part of mine.»

Taylor Swift
But as the crowds grew, those late-night signings were becoming increasingly more difficult to work in. It was clear that Taylor didn’t have the steeliness of a lot of starlets her age who were groomed for that by their parents almost from birth. Maybe because this whole massive career thing was her idea, she was clearly still digging it. In pretty much every picture, she looked like that person’s best friend since kindergarten. Every so often, with someone closer to her own age, she would say, ”Let’s do a funny one,” and urge the fan to screw up his or her face with her.
Taylor Swift (2008)

Tour Opening Act

Tour Opening Act 2006-2009 Taylor promoted her debut album, Taylor Swift (2006), by performing as an opening act for several major country artists’ concert tours, including Rascal Flatts, George Strait, Brad Paisley, Tim McGraw and Faith Hill, and Keith Urban.

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Nashville's New Superstar

In 2007, Taylor’s debut album was one of the Top 10 all-genre SoundScan sellers. And all those sales came in while a lot of non-country-lovers had yet to hear of her. Or, if they had, were still asking, ”Taylor Swift? Who’s he?” But she was harder to escape in mid-2008: Besides several smash hits at country radio, Taylor had moved into the upper levels of the Top 40 format with a remix of her heartbreak ballad ”Teardrops On My Guitar.” MTV was even playing it. Taylor was the most popular high school senior in America:

«This is a moment in time that I know is never gonna come again. And I’m just so thankful for everything that’s happened. I can think of a million names who have helped me get here. People who have stood in line to get my autograph, called and requested my song on the radio, helped me in some way, let me get up on a stage when I was ten years old. I think this whole time I’ve been dreaming of sitting right here and being able to tell you all the things that have happened in the last year, and have it be real. It’s real.»

Taylor Swift
Taylor won many accolades for Taylor Swift. She was one of the recipients of the Nashville Songwriters Association‘s “Songwriter/Artist of the Year” in 2007, becoming the youngest person to be honored with the title. She was even nominated for “Best New Artist” at the 2008 Grammy Awards and also won the Academy of Country Music Awards‘ “Top New Female Vocalist,” the American Music Awards‘ “Favorite Country Female Artist” honor, and the Country Music Association‘s “Horizon Award,” which she accepted through tears while saying, “This is definitely the highlight of my senior year.” Nashville knew: Taylor was country music’s new superstar.
General Information
Associated AlbumTaylor Swift
Beginning of EraJune 2006
End of Era
Tour
AestheticNashville
High school
Sharpie heart
Guitar
Teal
StyleSundresses
Cowboy boots
Florals
Sparkly prom dresses
Chokers
Skull necklace
Tight ringlets
ERA CHRONOLOGY
Taylor Swift Era (2006-2008)Fearless Era (2008-2010)
Taylor Swift Era

Taylor Swift (2006)

Taylor Swift Songs

Tour Opening Act

Taylor Swift: A Place In This World

Taylor's Discography