Originally, this film was not supposed to be a sequel to Road to Singapore (1940); in fact, Bing Crosby and Bob Hope were not even supposed to be in it. The film was first offered to Fred MacMurray and George Burns, who both rejected it. While assembling a list of contract Paramount stars to offer it to, someone at the studio remembered that "Road to Singapore" had done relatively well, and Hope and Crosby "seemed to work well together", and it was offered to them. The rest, as they say, is history.
Nominated in 1941 for "Best Picture" by the National Board of Review but did not win.
Chuck refers to dollars as "Morgenthau mash notes". When this film was made, Henry Morgenthau, Jr. was the U.S. Secretary of the Treasury, and had been an architect of the New Deal designed to end the Great Depression. All U.S. paper money printed at that time bore Morgenthau's signature. A "mash note" is a sentimental or effusive note or letter expressing affection for the recipient--i.e. a love note.
While playing the drums Chuck calls out the name "Chloe". This was a popular song of the day about searching for a lover in which the singer calls out the name.