Mathis sang at a pre-Grammy party hosted by Clive Davis in February 2015 and, "by almost all accounts, brought the house down and the crowd to its collective feet with his performance of his past hits." The appearance inspired the idea to have the singer make a concept album that Davis would executive produce and Kenneth "Babyface" Edmonds would produce, but instead of focusing on the Great American Songbook as Mathis has done throughout his career, the selections here date back only as far as the 1990s.