Christopher Walken's bar-top dance scene took two months of rehearsal and two days of shooting. He claims he got compliments later from fans Fred Astaire and Gene Kelly.
When asked in Rolling Stone about the film's box-office failure, Steve Martin said: "I'm disappointed that it didn't open as a blockbuster and I don't know what's to blame, other than it's me and not a comedy. I must say that the people who get the movie, in general, have been wise and intelligent; the people who don't get it are ignorant scum."
At least four paintings are re-created as "tableaux vivants" in the film: "Hudson Bay Fur Company" (1932) and "20 Cent Movie" (1936), both by Reginald Marsh, and "New York Movie" (1939) and "Nighthawks" (1942), both by Edward Hopper. Three of the four were painted after 1934, when the movie takes place, and all depict scenes in New York, not Chicago, the setting of the movie. Turner Classic Movies uses the "Fur Company" and "Nighthawks" shots in their "Open All Night" interstitial.
Around the time that this movie was made and released, the film's two lead stars Bernadette Peters and Steve Martin were in a personal relationship.
The "pennies" that are seen raining down from heaven are penny-sized sequins. After filming, they blew out the stage door and could be found in the corners in the streets at MGM studios for almost a year.