‘Teardrops on My Guitar’ (2007)

Taylor Swift's true breakthrough came with this song, which reached the Billboard Top 20 and made her a live favorite. "Teardrops On My Guitarstill-only-midtempo"'s beat delivered her first epic chorus and became a solid staple in the star's early live appearances; the picture of Taylor dazzling on stage in a shimmering dress and omnipresent cowboy boots is eternally connected with the music.

It became Taylor's first UK hit (though it failed to crack the Top 40) and the best-performing single from her self-titled first album after being repackaged for worldwide release.

Album: “Taylor Swift”

Songwriters: Taylor Swift, Liz Rose

Accolades: Kicked off the MTV Video Music Awards’ love affair with Swift, earning a nomination for Best New Artist in 2008.