Lyricist Jimmy Kennedy wrote "Red Sails In The Sunset" after watching a yacht with red sails off the coast of Ireland. British pianist, arranger and bandleader Lew Stone and his Orchestra were first to record "Red Sails In The Sunset" (Hugh Williams - Jimmy Kennedy) in 1935. This track is edited to include Joe Ferrie as the vocalist, he also played trombone in the orchestra. Co-writer Jimmy Kennedy wrote the lyric for "South Of The Border", "My Prayer", "Isle Of Capri", "Harbour Lights" and "Teddy Bear's Picnic".

Grammy and Academy Award winner Bing (Harry) Crosby topped the charts in 1935 with his version of "Red Sails In The Sunset". The single aided his career as the leader in record sales and film grosses from 1931 to 1954.

The late Nat "King" Cole had success with his version of "Red Sails In The Sunset" in 1951 when he reached number twenty-four on Billboard. Wikipedia: "In August 1948, Cole purchased a house from Col. Harry Gantz, the former husband of the silent film actress Lois Weber, in the all-white Hancock Park neighborhood of Los Angeles. The Ku Klux Klan, which was active in Los Angeles in the 1950s, responded by placing a burning cross on his front lawn. Members of the property-owners association told Cole they did not want any "undesirables" moving into the neighborhood. Cole responded, "Neither do I. And if I see anybody undesirable coming in here, I'll be the first to complain."