Throughout his solo career, Paul McCartney has consistently pursued diverse artistic directions rather than limiting himself to a single commercial formula. After years of experimenting with vintage musical influences, he eventually committed to recording an entire album of jazz standards, having long admired the structural elegance and artistry of classic songwriters such as Harold Arlen and Cole Porter.

Undeterred by the knowledge that his traditional rock audience would not embrace the project, McCartney proceeded with his vision of performing sophisticated popular songs that had influenced him throughout his life. His deep respect for performers like Frank Sinatra and Fred Astaire informed his approach to capturing the refinement of these compositions, making the creative fulfilment of this longtime goal more important than commercial approval from his established fanbase.