“Sailing” is a 1980 soft rock song written and recorded by American artist Christopher Cross. It was released in June 1980 as the second single from his eponymous debut album (1979). The song was a success in the US, reaching #1 on the Billboard Hot 100 chart on August 30, 1980. 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. VH1 named “Sailing” the most “softsational soft rock” song of all time.
The song was recorded in 1979, utilizing the 3M Digital Recording System, making it one of the first digitally recorded songs to chart. 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. The song was later identified as an archetype of the style that later became known as yacht rock (Cross and similar artists referred to the style as the West Coast sound at the time).
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. Glasscock functioned as a surrogate older brother during a tough time for Cross emotionally. Although Cross lost touch with Glasscock, The Howard Stern Show in April 1995 reunited Cross with Glasscock, 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.”