Sailing

Christopher Cross wrote "Sailing" about an older friend from his high school years, Al Glasscock, who would take him sailing as a teenager to get away from the troubles of adolescence. Glasscock functioned as a surrogate older brother during an emotionally difficult period for Cross. The two lost touch, though The Howard Stern Show reunited them in April 1995 after 28 years apart, and Cross confirmed on air that those sailing trips had inspired the song. He later sent Glasscock a copy of the platinum record he earned for selling more than five million copies of the single.

The song was written and recorded in 1979 and released in May 1980 as the second single from Cross's debut album, which had already gone gold. It reached number one on the Billboard Hot 100 on August 30, 1980, holding the spot for one week. At the Grammy Awards it won Record of the Year, Song of the Year, and Arrangement of the Year, and helped Cross take the Best New Artist prize. In his acceptance speech, Cross called it his favorite song on the album and said it had not originally been intended as a single.

The recording used the 3M Digital Recording System, making it one of the first digitally recorded songs to chart. Cross also said the orchestral beginning was the result of a wrong button being pushed during recording, with the acoustic guitar part, which was meant to open the song, catching up to it afterward.