"When the Sun Goes Down" is a song written by Brett James and recorded by American country music artist Kenny Chesney as a duet with Uncle Kracker. It was released in February 2004 as the second single and title track from Chesney's 2004 album of the same name. The song reached number one on the US Billboard Hot Country Singles & Tracks chart on April 3, holding the number one position for five weeks. It also reached number 26 on the Billboard Hot 100. It was Uncle Kracker's first appearance on the country music charts, his next one being "Smile".