Love Story’ (2008)

'Love Story,' which Taylor wrote in just twenty minutes while sitting on her bedroom floor, became one of her biggest hits and is now one of her most memorable songs.

In this high school retelling of Romeo and Juliet, Shakespeare meets country music. While the star-crossed fairy-tale relationship that prompted Taylor to create the song never came to fruition, the same relationship led Taylor to write 'White Horse' from the same album.

Most foreign listeners would choose "Love Story," which was released before she became famous, as the song that initially made them aware of the budding star. Taylor was still in her teens when the video was aired, and she was presented as a romantic princess in it — an unusual twist on the identity that the frenzied tabloids would grasp and alter in the years to come. While "Love Story" is still recognizable as a country song, its unabashedly pop production helped it become a massive radio smash, and the song was extensively nominated during awards season. It was Taylor's first commercial hit, reaching No. 1 in Australia, No. 2 in the United Kingdom, and No. 5 in the United States.

Album: “Fearless”

Songwriter: Taylor Swift

Accolades: “Love Story” took Best Music Video at the CMT Music Awards and the Country Music Association Awards.