On Oct. 24, 2006, a little-known singer-songwriter from Wyomissing, Penn., released her self-titled debut album. That 16-year-old was Taylor Swift, who obviously went on to become one of the most successful and influential recording artists of the past two decades — shattering sales, chart, and box-office records.
But 17 years before she was selling out a historic six-night Eras Tour run at Los Angeles’s SoFi Stadium (and four months before Taylor Swift came out), she performed at Yahoo Entertainment’s office in Santa Monica, Calif., on July 12, 2006. She was in her very first era, just a kid with corkscrew curls, cherub cheeks, and a dream.
A little more than a month later, on Aug. 21, 2006, Swift was in our Los Angeles studio to shoot one of her first major promotional performances — for Yahoo’s rising artist program “Who’s Next?” — and she seemed grateful for the opportunity, even changing one of the lines in her future hit “Tim McGraw” to “When you turn Yahoo Music on.” (Catch that shout-out at the 3:09 mark in the video below.) A clip from the performance was later included in her 2020 documentary Miss Americana.
“I decided I wanted a record deal when I was 10 years old,” she told us at the time, 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 Swift was only beginning her musical career (on Scott Borchetta’s Nashville record label Big Machine, with which she has since famously, acrimoniously parted ways), 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 Swift would be romantically linked with Joe Jonas, John Mayer, Calvin Harris, Tom Hiddleston, Harry Styles, Jake Gyllenhaal, Joe Alwyn, or most recently Travis Kelce, but her lovelorn lyrics, seemingly ripped 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,” she 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 Swift’s first crossover pop hit, the VMAs-winning (and Kanye “Ye” West-antagonizing) “You Belong With Me,” also came up in the conversation. “I had a lot of trouble in school. I was really different,” she 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 me, 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.”
After Taylor Swift went gold — obviously the beginning of a very long list of RIAA certifications in her 114 million-selling career — Swift visited Yahoo’s Northern California headquarters in Sunnyvale in 2007, to play a thank-you lunchtime concert on the campus lawn and present Yahoo with a gold plaque.
“Because Yahoo had such a huge hand in everything that’s happened and the gold record that I have hanging on my wall at home, I wanted to present one to… everyone at Yahoo. I mean, thank you so much,” she gushed, before leading the quad in the Yahoo yodel.
You’re welcome, Taylor!
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