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The working titles of this film were Sylvester, The Great, Treasure Chest and The Mad Pirate. According to June and August 1941 Hollywood Reporter news items, Fred Astaire was considered for a starring role opposite Bob Hope, and Sy Bartlett, Niven Busch and Norman Panama were originally slated to collaborate on the screenplay with Melvin Frank. Only Bartlett received screen credit, and the contribution of the other writers, if any, has not been determined. Later 1941 items cite Sam Wood as a possible director, and Nat Perrin as another possible writer. In March 1944, Constance Dowling was announced as Hope's female co-star.
A May 1944 Hollywood Reporter news item lists Art Foster as a member of the film's cast, but his appearance in the final film cannot be confirmed. In April 1944, Hollywood Reporter reported that Hope's character was to be named "Sylvester Crosby" as a nod to Bing Crosby's uncredited appearance at the end of the film as the "commoner" but Hope is only called "Sylvester" in the film. Studio promotional materials asked reviewers not to reveal the film's ending, and not to review the picture until its release in November 1944. The film received Academy Award nominations in the Art Direction (Color) and Music (Music Score of a Dramatic or Comedy Picture) categories.