This album is the result of a historic collaboration between Count Basie and Frank Sinatra, recorded in a single session on August 9, 1964, at A&R Studios in New York. Basie's orchestra, at its peak, provided the perfect accompaniment for Sinatra's voice, who had returned to Columbia Records after his stint at Capitol.
The repertoire includes standards from the Great American Songbook, with arrangements by Quincy Jones and Billy Byers. The session was produced by Teo Macero, known for his work with Miles Davis, and the album reached number 13 on the Billboard 200 chart.
Although the title suggests a lighthearted tone, the recording was meticulously planned. Sinatra and Basie had previously collaborated in 1962 on the album 'Sinatra-Basie', but this record solidified their musical chemistry, being acclaimed by critics as one of the best works of both artists.