Flashback Interview: Taylor Swift Visits Yahoo Music at Age 16

Ten years ago, on Oct. 24, 2006, a little singer-songwriter from Wyomissing, Pennsylvania, released her debut album, Taylor Swift. Obviously, she went on to become one of the most massive recording stars of the past 20 years, shattering sales and chart records — first in country music, before crossing over even more successfully into pop. But when Taylor Swift visited Yahoo Music a decade ago to promote her album, she was just a 16-year-old with corkscrew curls, cherub cheeks, and a dream.

“I decided I wanted a record deal when I was 10 years old,” she told Yahoo Music, sounding incredibly well-spoken and grounded even at such a young age. “I came to Nashville for the first time when I was 11 and had this little demo CD of me singing Dixie Chicks songs, and walked into every major record label and was like, ‘Hey, I’m Taylor. I’m 11. I want a record deal. Call me.’”

Interestingly, even though she was only beginning her musical career (on Scott Borchetta’s Nashville record label, Big Machine), in her Yahoo interview she addressed two themes that would remain prevalent in both her music and her personal narrative: boyfriends and bullying.

It was years before she’d be romantically linked with Calvin Harris, Tom Hiddleston, Harry Styles, Jake Gyllenhaal, et al, but her lovelorn lyrics, seemingly torn from the pages of her teenage diary, were already garnering early attention. “A lot people look at me, and they’re like, ‘You’re 16. How many boyfriends have you had?’ I haven’t had that many boyfriends at all,” Swift laughed. “I just like to take example of what my friends are going through, or examples of what the couple next door is going through. Songwriting is a lot more observing that it is experiencing in some cases.”

The outsider/misfit theme that was at the center of her first crossover pop hit, the VMA-winning “You Belong With Me,” also came up in this 2006 conversation. “I had a lot of trouble in school. I was really different,” Swift revealed. “I was taller, and I sang country music — and apparently that wasn’t the genre of choice for middle-schoolers in Wyomissing, Pennsylvania, at the time. I got a lot of grief for it. And I think at that point I came to a crossroads in my life… I had to turn it into something positive. And for, that was songwriting.

“You know, those people who were mean to me back then in middle school write me these really sweet emails now about how they wish me luck. You’ve got a little part of you that wants to be like, ‘Remember what you did?’ But you’ve got to thank them for making who you are today, and for making you strong.”