Pop Song 171 'Sailing' Christopher Cross 1979

Pop Song 171 'Sailing' Christopher Cross 1979

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."