Louis Armstrong (August 4, 1901-July 6, 1971) and Bing Crosby (May 3, 1903-October 14, 1977) were two of the greatest American singers and showmen of all time (Louis was also one of the most influential jazzmen ever). They were also close friends who shared a mutual admiration. Although their personal relationship may well have begun earlier at some theatre or club performance featuring one of the two musicians they first collaborated together on Crosby s feature film Pennies from Heaven. Although Bing and Louis appeared together in a few scenes, they didn t sing a duet together in that film (Louis s sole showcase performance featured him playing A Skeleton in the Closet ). However, when Decca issued a couple of singles with music from the film, both Louis and Bing sang on the title tune Pennies from Heaven . Crosby was a great admirer of Louis and in the 1940 s and 1950 s asked for his participation in his movies or radio and television shows as often as possible. Their most memorable collaborations, however, were still to come. The first was their participation in the Hollywood production of High Society (1956), a film with a soundtrack by Cole Porter (which he composed especially for the movie). The film also featured Frank Sinatra and Grace Kelly in what was to be her last film appearance before moving to Monaco to become queen. The four figures shared star billing on the promotional posters, and the sequence involving Armstrong and Crosby singing Now You Has Jazz together was among the most popular scenes of the film. Their other important collaboration (which was also to be their last) was a proper duet LP that was proposed and financed by Bing Crosby himself in 1960: Bing and Satchmo. Crosby wanted everything to be perfect, and looked for a well balanced and cohesive album instead of a collection of separate songs with roughly arranged duets. The talented Billy May was called in to do the arrangements, and Johnny Mercer acted as a kind of producer, adding supplementary lyrics to nearly all of the songs and even singing a single uncredited line on Lazy River . Mercer s new lyrics gave unity to the album as a whole, creating the impression of a whole stage show rather than a compilation of individual performances. The album marked Louis Armstrong s only collaboration ever with Billy May.