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.
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:
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.”
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:
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.”
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:
Taylor was on a homeschooling program which allowed 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.
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:
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:
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 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.