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Teardrops on My Guitar" is a song by American singer-songwriter Taylor Swift. The song was written by Swift and Liz Rose, and produced by Nathan Chapman. "Teardrops on My Guitar" was released on February 19, 2007 by Big Machine Records, as the second single from Swift's eponymous debut album (2006). The song was later included on the international release of Swift's second studio album, Fearless (2008), and released as the second pop single from the album in the United Kingdom. It was inspired by Swift's experience with Drew Hardwick, a classmate of hers for whom she had feelings. He was completely unaware and continually spoke about his girlfriend to Swift, something she pretended to be endeared by. Years afterwards, Hardwick appeared at Swift's house, but Swift rejected him. Musically, the track is soft and is primarily guided by a gentle acoustic guitar. Critics have queried the song's classification as country music, with those in agreement (such as Grady Smith of Rolling Stone) citing the themes and narrative style as country-influenced and those opposed (such as Roger Holland of PopMatters) indicating the pop music production and instrumentation lack traditional country elements.
Critics received the track generally positively, complimenting Swift's vocal delivery and songwriting style. The song is considered to be Swift's breakthrough single, as it spread her popularity throughout the United States. "Teardrops on My Guitar" was commercially successful, peaking at number 13 on the Billboard Hot 100, becoming the best-charting single from Taylor Swift on the chart, and being Swift's debut entry on the Billboard Year-End Hot 100 charts. The single was also certified triple platinum by the Recording Industry Association of America (RIAA). Its music video was directed by Trey Fanjoy and features Swift as she sees her love interest develop a relationship with another female. The video received a nomination for MTV Video Music Award for Best New Artist, but lost to Tokio Hotel's music video for "Ready, Set, Go!". The song was promoted through multiple live performances, some while supporting as opening act for various country artists' concert tours. She also performed "Teardrops on My Guitar" on her first headlining tour, the Fearless Tour (2009–10).
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