Taylor Swift, ‘Teardrops on My Guitar’ – Video Flashback

Taylor Swift's musical style matches her personality -- innocent but honest, sweet yet sassy -- and all of that is evident in her 'Teardrops on My Guitar' video. No one wants to see the good guy get hurt, and in this instance, the pop-country superstar is the underdog. She's hopeful that her crush, Drew -- played by Tyler Hilton -- will ask her out, but his eyes roam elsewhere. So alone in her room she sits, strumming her guitar and writing her next big hit as she cries and longs for his attention.

'Teardrops on My Guitar' was the second single from Swift's self-titled debut album, following 'Tim McGraw.' 'Teardrops on My Guitar' peaked at No. 2 on Billboard's Hot Country Songs chart, and No. 13 on Billboard's Hot 100, laying down the foundation for a path to success that Swift would soon find in both country and pop music. A slew of No. 1 hits would follow the 2007 single, including 'Love Story' and 'Mine.'

Though most of her songs are set in high school, Swift's music is so popular because it's universally relatable -- and when chemistry class is a distant memory and laughs in the library are no more, at some point, everyone aches for that special person who is just out of reach. In the 'Teardrops on My Guitar' video, we all feel for the bedazzled Taylor as she lays in bed with her guitar and asks, "I wonder if he knows he's all I think about at night?"

Watch the Taylor Swift 'Teardrops on My Guitar' Video