Circa 2003

Country's Determined Darling

At 13, Taylor Swift, who began writing songs at age 5, signs with RCA Records. A year later, she gets out of the contract because she doesn't want to sing other writer's songs. Around that time, she becomes the youngest songwriter to sign a publishing deal with Sony – but doesn't want her songs sung by other artists. "She has a real inner vision, a real inner directedness," says Scott Borchetta, who eventually urges Swift to write and sing under a recording contract with his indie label, Big Machine Records.

2006

Swift's "Tim McGraw"

Swift's breakout single, "Tim McGraw," which she began writing in her freshman math class, hits country radio airwaves. The song is about hoping her love thinks of her when he hears Tim McGraw's music. It peaks at No. 6 on the Billboard Hot Country Songs chart. While performing her hit at the Academy of Country Music Awards in 2007, Swift finally meets McGraw when she walks into the audience to serenade McGraw and his wife, Faith Hill (right).

October 24