Having directed Jack Benny's finest screen performance in To Be or Not to Be, the legendary Ernst Lubitsch oversaw retakes of this later film between early November and November 10, 1942. Writer Morrie Ryskind, who had worked on the early stages of the screenplay, was brought back to create new dialogue for the retakes. Neither contributor received an opening credit.

In March 1943, when the film was in wide release, a lawsuit brought by a group of lawyers from New Haven, Connecticut charged that this comedy "showed the legal profession in a disreputable light." The complainants asked for the movie to be withdrawn, but their plea was thrown out by Connecticut Superior Court Judge Patrick O'Sullivan.

On July 8, 1942, both The Hollywood Reporter and Daily Variety revealed that Twentieth Century-Fox was scrapping the film despite an investment of about $150,000 so far. The next day, The Hollywood Reporter described Jack Benny as being unhappy with some of the screenplay, which Mr. Benny complained was too juvenile. For this project, Fox had given Jack approval of the script, director and co-star. Mr. Benny and the studio quickly settled their differences, and shooting began on July 22, 1942, with principal photography lasting into early September.

The film was edited down to one of the shortest "A" features of the Forties, with a running time of merely 57 minutes. According to The Motion Picture Herald Production Digest, the movie's brief duration caused booking problems.

The original Broadway production of "The Meanest Man in the World" by Augustin MacHugh opened at the Hudson Theater on October 20, 1920 starring George M. Cohan and ran for 202 performances.

Twentieth Century-Fox originally had penciled in Maureen O'Hara to portray Janie Brown. Ultimately, the studio would borrow Priscilla Lane from Warner Bros. Walter Lang, the first choice to direct, had to bow out due to illness. As his replacement, Sidney Lanfield, a Fox contract director between 1930 and 1939, was called in from his current studio, Paramount.