"Sailing" is a 1979 soft rock song written and recorded by American artist Christopher Cross. It was released in June 1980 as the second single from his debut album Christopher Cross (1979), which was already certified Gold by this time. The song was a success in the United States, reaching number one on the Billboard Hot 100 chart on August 30, 1980, where it stayed for one week.^[1][2] The song also won Grammy Awards for Record of the Year, Song of the Year, and Arrangement of the Year, and helped Cross win the Best New Artist award.^[3] VH1 named "Sailing" the most "softsational soft rock" song of all time.^[4]

The song was recorded in 1979, utilizing the 3M Digital Recording System, making it one of the first digitally recorded songs to chart.^[5] In his Grammy acceptance speech, Cross acknowledged "Sailing" as his favorite song on the album and that originally it was not meant to be a single.^[6] The song was later identified as an archetype of the style that later became known as yacht rock^[7] (At the time Cross and similar artists referred to the style as the West Coast sound).^[8]

Cross has said in interviews that the song's inspiration was his friendship with an older friend from his high school, Al Glasscock, who would take him sailing as a teenager, just to get away from the trials and tribulations of being a teenager.^{[9] [10]} Glasscock functioned as a surrogate older brother during a tough time for Cross emotionally.^[11] Although Cross lost touch with Glasscock, The Howard Stern Show in April 1995 reunited the two after 28 years. Cross acknowledged on the show that his sailing trips with Glasscock had been the inspiration for the song. After that reunion, Cross sent Glasscock a copy of the platinum record he earned for selling more than five million copies of "Sailing."^[11]

• "Sailing" was covered in 1997 by American boy band NSYNC on their eponymous debut studio album.^[12] NSYNC and Christopher Cross performed the song together at the 1999 Blockbuster Entertainment Awards.^[13]

• "Sailing" was sampled on "Bagsy Not in Net" by the 1975 from their album Notes on a Conditional Form.^[14]

• The song was sampled on Puff Daddy's song "Best Friend" from his 1999 album Forever.

• The song was sampled on Krayzie Bone's song "Paradise" released in 2008.

• The song can be partially heard in the 2022 Michael Bay movie Ambulance.^[15]

• Also covered by George Benson on his album, Songs and Stories.

• Christopher Cross – vocals, 12-string electric guitar, arrangements
• Andy Salmon – bass
• Michael Omartian – acoustic piano, arrangements
• Rob Meurer – electric piano, arrangements
• Victor Feldman – percussion
• Tommy Taylor – drums

• List of Billboard Hot 100 number-one singles of 1980