As with all of Newman's early albums, several of its songs had been previously recorded by other artists. In this case, "Simon Smith and the Amazing Dancing Bear" had been a UK hit for Alan Price in 1967, and "Dayton, Ohio - 1903" had been recorded by Harry Nilsson on his 1970 album Nilsson Sings Newman and also by Billy J Kramer. Newman himself had also previously recorded "Last Night I Had A Dream" as a single, issued in September 1968. The version heard on Sail Away is a re-recording with a notably different arrangement.
The song "Lonely at the Top" was written specifically with Frank Sinatra in mind, although he never recorded it.