In 1942, Fred Astaire and Bing Crosby teamed up at Der Bingle's Paramount Pictures for Holiday Inn, a black-and-white musical that proves more entertaining than Crosby's color semi-remake White Christmas in 1954. Astaire and Crosby play partner/rival song-and-dance men who compete for the hand of their performing partner, played by Virginia Dale. After Crosby loses, he moves to the Connecticut countryside where he creates a resort that is only open on holidays and puts on the shows with the help of Marjorie Reynolds. Dumped by Dale, Astaire makes a drunken arrival at the inn on New Year's Eve and dances with Reynolds. He decides she'll be his new partner, but doesn't remember what she looks like, setting off a frenzied search at every subsequent show while the once-bitten Crosby does his best to steer him off track.

The theme gives Irving Berlin an excuse to craft or recycle a number of holiday-themed songs, such as (in the former category) "Washington's Birthday" or (in the latter) "Easter Parade." The most famous of the new material, of course, is "White Christmas," which became one of the best selling songs of all time and the title song of Crosby's 1954 film. Astaire and Crosby also team up for "I'll Capture Her Heart," which playfully contrasts the stars' specialties, and Astaire's "It's So Easy to Dance with You" became one of the signature songs of his post-Ginger Rogers career. Astaire and Crosby teamed up again for Blue Skies in 1946.