The "pennies" that are seen raining down from heaven were 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.
At least four paintings are recreated 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.
In the scene in the classroom, miniature flags of several nations are sitting on the desk. The Canadian flag, however, is inaccurate because the Red Maple Leaf flag used was only created in the 1960s and became Canada's official flag in 1965 many years after "Pennies from Heaven" took place.
Hollywood veteran of musicals Fred Astaire did not want the re-use of his old film footage which he was powerless to stop and as such resented the film. Astaire once said of this: "I have never spent two more miserable hours in my life. Every scene was cheap and vulgar. They don't realize that the thirties were a very innocent age, and that [the film] should have been set in the eighties - it was just froth; it makes you cry it's so distasteful."
Producer Nora Kaye once said of Steve Martin's casting: "If you just had a terrific actor, the musical numbers wouldn't come off. Steve knows how to put across the number. He's right for the part in another sense, too. In the '30s all the leading men were classic American types. But today, there are very few stars who are not ethnic - either Italian or Jewish. You kind of feel Steve is a Baptist, and that's what this story needs. He's so guileless, like a Capra hero."
The MGM studio prohibited the broadcast of the BBC's original production Pennies from Heaven (1978) for a period of ten years after this movie premiered. In February 1990, the BBC aired the original for the first time since 1978. This only happened because around 1989, at the direction of Alan Yentob of BBC2, producer Kenith Trodd bought back from MGM the rights for "a very inconsiderable sum".
To prepare for his dancing role in this MGM musical, Steve Martin trained in tap-dancing for six months. Christopher Walken had already trained as a dancer when younger and as such could draw on those dancing skills he had already learned.
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."
Sets designed by Ken Adam for this movie included a dilapidated farmhouse, a smokey Chicago speakeasy, and an art decor bank, and an exact replica of a set used in the RKO musical Follow the Fleet (1936).