Songfacts®:

• This 2:32 track finds Newman in character as successful singer who despite the money and adulation, isn't happy. Newman wrote it for Frank Sinatra; both were signed to Warner Bros. Records, which was looking to find Sinatra a hit. The song is essentially a satire of Sinatra's image; it didn't fly with Old Blue Eyes, so Newman cut it himself for his album Sail Away.
  
  Speaking with Rolling Stone, Newman explained: "I thought - maybe stupidly - that he would be ready to make fun of that leaning-against-the-lamp-post s--t: 'Oh, I'm so lonely and miserable and the biggest singer in the world.' I never bought that part of him. I thought he'd appreciate that. I played it for him, at his office on the Warner Bros. lot. His reaction? Nothing. He said, 'Next.' I also played 'I Think It's Going to Rain Today.' He said, 'I like that one.' But he couldn't hide his bitterness at young people's music."
• Mojo magazine September 2008 asked Newman if he was concerned that Sinatra might take offense at this song's mockery of his public image that he'd carefully built over decades. He replied: "Yeah, it's amazing that I thought he'd do it, and I actually played it for him. But I think he was intelligent enough to laugh at the whole premise of the rich guy at the top who's lonely and unhappy. I played it for Streisand and she said, 'Well ha ha…' She liked it but thought people would believe she meant it. And it suddenly dawns on me that's why I'll never exactly win the love of the American public! They want artists to mean what they say! I don't give them that; I'm interested in something else. I like the way I write and wouldn't change it."