The collection features Kelly performing songs from nine of his albums, along with the previously unreleased track "True to You" and a cover of Cole Porter's "Every Time We Say Goodbye" to new interpretations by Grabowsky.

[4][5] The album was announced on 17 June 2020 and in a press statement, Grabowsky said "The performances are intimate, and shine a light on lyrical moments from the Kelly oeuvre.

"[6][7] Grabowsky said the album was inspired by Frank Sinatra, Nelson Riddle, Bill Evans and Tony Bennett.

[8] In the early 1990s, Kelly was booked to perform "Winter Coat" on The Steve Vizard show in which Grabowsky was the musical director.

The duo first worked together on a project with the Australian Art Orchestra, called Meet Me in the Middle of the Air, which involved a ten-piece ensemble, Vika and Linda Bull and Kelly singing Grabowsky's arrangements of songs of his which all had biblical references.

In 2019, Grabowsky was asked to curate a series of concerts at the UKARIA Cultural Centre in Mt Barker, South Australia, in which I work in duo settings with various singers.

"[10] Jeff Jenkins from Stack said "This affair follows a similar formula (to 2019s Tryst with Kate Ceberano): Grabowsky's peerless piano playing accompanying one voice (and some occasional harmonica).