In spring 2016, Chenoweth announced via Twitter that she was working on a new studio album, set to be released in spring 2017. The release date was pushed forwards though, and in mid-August, Chenoweth announced via social media that it would be released on September 23, 2016.[1] The following week she announced the title, and shortly afterwards released the cover photo.[2]
Chenoweth revealed that the recording would be covers of selections from the Great American Songbook, and released the first single, "The Very Thought of You" on August 19.[3] A second single, "Smile" was released on September 9.
This album also marks Chenoweth's second Great American Songbook-themed album. Her first was her 2001 debut album Let Yourself Go, which featured mostly classic songs from the 1940s.