Lucille Ball wanted to play Katherine 'Sugarpuss' O'Shea, as she thought it was the kind of role that would win her an Oscar. She fought for the role and was eventually hired, but once producer Samuel Goldwyn found out that Barbara Stanwyck was available he gave her the part instead.
To pick up authentic slang for the film script, screenwriters Billy Wilder and Charles Brackett visited the drugstore across the street from Hollywood High School, a burlesque house and the Hollywood Park racetrack.
In the scene where Pastrami and Asthma have the professors hostage in the library, the gunmen begin shooting at random items. One gunman (Pastrami) says, "I saw me a picture last week," and proceeds to lick his thumb and then rubs it on the sight of his gun. This is a reference to star Gary Cooper's previous movie Sergeant York (1941) in which York uses this as a technique to improve his marksmanship.
Even though they play two of the "old men" lexicographers, Leonid Kinskey (Prof. Quintana) and Richard Haydn (Prof. Oddly) were both under 40 years old when they made this movie and, therefore, younger than Gary Cooper.
Producer Samuel Goldwyn promised director Billy Wilder a $10,000 bonus if the film became a box-office hit. When it was released in theaters, it was an instant success. One day Wilder stopped by Goldwyn's office and asked for his $10,000 bonus. Goldwyn flew into a rage. "You Hungarian thief!" he shouted at Wilder. "I never promised any such thing! Get out of here!" Wilder left the office, furious. That night, however, Goldwyn's wife, Helen, awoke to find him pacing the floor of their bedroom. "I've just remembered that Wilder was right," Goldwyn told her. "I DID promise him a $10,000 bonus." "What are you going to do?" asked Helen. "What CAN I do?" Goldwyn replied. "I'm going to sit down here and write Wilder a check for $5,000!"
Howard Hawks recalled that for the scene in which Bertram reveals his feelings about Sugarpuss in the darkened bungalow, cinematographer Gregg Toland coated Barbara Stanwyck's face with black grease paint so that her eyes would stand out.
Dana Andrews based his character of Joe Lilac--Sugarpuss O'Shea's boyfriend--on notorious gangster Bugsy Siegel. Siegel owned the Formosa, a club across the street from Goldwyn Studios, and Andrews used to go there after work. He had the suits, the hats, right down to the spats, down pat.
Several cast members in studio records/casting call lists for this movie were not seen in the final print. These were (with their character names): Lee Phelps (Policeman in Station), Johnnie Morris (Clerk at Justice of the Peace), Dick Rush (Policeman at Motor Inn), Del Lawrence (Irish Gardener) and Jack Perry (Fighting Bum).