This was the first recording that Sinatra made with the Count Basie Orchestra. In 1964, Sinatra and Basie would make a final studio recording, It Might as Well Be Swing, orchestrated by Quincy Jones, and Sinatra's first live album, Sinatra at the Sands (1966) would feature the Basie band.

Sinatra appeared on an episode of The Dinah Shore Show that aired on December 9, 1962, the day before Sinatra-Basie was released, and performed the album's arrangement of "Please Be Kind".

According to Will Friedwald's book, Sinatra! The Song Is You, "Basie didn't play piano on several of the tracks: 'The day before the first date, we rehearsed all day, all night', said Bill Miller, officially serving as contractor. 'Everybody also came in an hour before so we could go over them again.' As Joe Bushkin has pointed out, 'The Basie guys could read as well as any studio band', but to help them nail the charts even tighter, Sinatra and Miller brought in ace lead trumpeter Al Porcino. Basie was a capable but not an expert reader, Miller continued, 'and he was very slow to learn new tunes, so on a couple of the songs, he said, "You play it."' Long story short, Bill Miller played piano on 'Pennies from Heaven.'"

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