Bing Crosby and Bob Hope met briefly for the first time on the streets of New York in the summer of 1932. In December, both performed at the Capitol Theater in New York, as the newspaper ad to the right reveals. There for the first time Crosby and Hope performed together, doing an old vaudeville routine that included two farmers meeting on the street. They did not work together again until 1938, when Bing invited Bob to guest on his radio program and to appear with him at the opening of the Del Mar race track north of San Diego. The boys reprised some old vaudeville routines that proved quite amusing to the celebrity audience. One of the attendees was the production chief of Paramount Pictures. He began searching for a movie vehicle for Hope and Crosby. He dusted off an old script intended originally for Burns and Allen, then later Jack Oakie and Fred MacMurray, and, now, Hope and Crosby. The tentative title was "Road to Mandalay," but the destination was eventually changed to Singapore.

To add a love interest to the movie one of the leading Paramount stars, Dorothy Lamour, was written into the script. Dorothy had appeared with Bob in "The Big Broadcast of 1938," but had never appeared in a film with Bing. Dorothy was known for her sultry singing voice and the skimpy South Sea outfits called sarongs that she wore in a couple of her movies. Although "The Road to Singapore" turned out to be the least zany of the Road pictures, the chemistry of the stars turned it into a blockbuster hit.

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