Yes, Bing Crosby sings songs written by Irving Berlin in Blue Skies (1946), all 32 of them, with Fred Astaire dancing to the tune of Puttin’ on the Ritz. Both guys duet on A Couple of Songs and Dance Men.
Other memorable Berlin songs in Blue Skies: A Pretty Girl is Like a Melody, White Christmas, Heat Wave, How Deep is the Ocean, All by Myself, You Keep Coming Back Like a Song and of course Blue Skies, the theme of the movie.
‘It’s the nearest thing to heaven’ is how Paramount hyped Blue Skies. – RKC