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"Sailing" is a song written and recorded by American artist Christopher Cross. It was released in June 1980 as the second single from his eponymous debut album. The song was a success in the USA, winning Grammy Awards for Record of the Year, Song of the Year, and Arrangement of the Year, and helping Cross win the Best New Artist award. VH1 named this the greatest "softsational soft rock" music song of all time.
It was a number-one rated single in the United States. Since its debut, it has been covered by many artists, including Avant, Barry Manilow, Greenskeepers, 'N Sync, Phajja, Patrick Yandalland, as a duo, Moya Brennan & Cormac de Barra. The song was one of the first digitally recorded songs, utilizing the 3M digital recording system. In his Grammy acceptance speech, Christopher acknowledged Sailing as his favorite song on the album and that originally it was not meant to be a single.
"Sailing" has been sampled in several other songs, including Puff Daddy's "Best Friend" (1999) and Bone Thugs-n-Harmony's "Paradise" (2006), and Chris Brown's "Can't Let You Go." Dr. Octagon's song "Blue Flowers Revisited" (1996) contains a brief interpolation of the chorus.