 In January 2019, it was announced that Connick was hired by piano instruction software company Playground Sessions as a video instructor.On October 25, 2019 he released a new album of Cole Porter compositions rearranged by Connick himself from Porter’s The Great American Songbook including “Anything Goes” and “You Do Something To Me.” After selecting the songs, and writing and orchestrating the arrangements, he assembled and conducted the orchestra which features his longtime touring band with additional horns and a full string section.Along with his album, Connick announced his return to Broadway on September 16, 2019 with "Harry Connick Jr. — A Celebration of Cole Porter", a multimedia celebration of the Cole Porter songbook.