The film was based on Irving Berlin's idea for a musical revue in the 1930s, where each number would be based on a different holiday. Me mentioned it to director-producer Mark Sandrich and they tailored it for Bing Crosby. Berlin demanded, and got, total artistic control over all musical elements, including casting, story, and discussions with Astaire about choreography.

The film was remade as "White Christmas," also starring Bing Crosby.

Marjorie Reynolds singing was dubbed by Martha Mears.

Joan Leslie was brought in from Warner Brothers to test as Fred's partner. He was very pleased with her, and remarked, "If Joan can't do this picture, we'll do another some time." She was unable to do the picture, but when Fred signed to do "The Sky's The Limit" he made certain to specify her as his partner.

The animated Thanksgiving sequence is a topical reference to President Roosevelt's failed attempt to change the date of the holiday.

The script originally called for a Labor Day dance number, "This Is a Great Country."

Fred Astaire, ever the perfectionist, took two slugs of bourbon before the first take and a slug of bourbon before each subsequent take of his "drunk dance" to ensure that his steps wouldn't be too perfect. The take used is the seventh and last take.

The firecracker dance, despite its improvisional storyline, was filmed 38 times before Astaire was satisfied.

According to AMC: Watching the firecracker dance from the wings was a young dancer who’d just arrived in Hollywood by way of Broadway. He took in all of Astaire’s fancy footwork with typical ingénue awe. Then, just like in a Hollywood fairy tale, Astaire noticed him. Astaire asked him if he could dance. “Yeah, I guess I can dance alright,” replied the star-struck young man. The two struck up a conversation and eventually became good friends. The young kid's name? Gene Kelly. (Thanks to David Abrams for the above)

"White Christmas" won the Academy Award for Best Song. The movie was also nominated for Best Original Story and Best Scoring of a Musical Picture.