#40. ‘When The Sun Goes Down’ by Kenny Chesney

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The most famous singles on Kenny Chesney’s 2004 record include “There Goes My Life,” “I Go Back,” “The Woman with You,” and the titular track, which is a duet with Uncle Kracker. “When The Sun Goes Down” climbed a couple Billboard charts, and its music video featured shots of Chesney playing in small venues as part of his Keg in the Closet tour. The song “There Goes My Life” is about a high school teenager who finds out his girlfriend is pregnant. The song’s music video includes the actress Amber Heard as the couple’s teenage daughter.