Fascinated by musical theatre from a young age, Fitzgerald perceived an intersection between entertainment and morality that characterised his presentation of popular culture. In 1939, Fitzgerald wrote to his daughter:

As a member of the Triangle Club at Princeton, he wrote the libretti for three musical comedies, and as a student at the Newman School in New Jersey from the ages of 15 to 17, he made the forty-minute journey into New York City often to see the latest musical comedies on Broadway. Fitzgerald grew up amidst something of a golden period of musical theatre composers and lyricists, and he also witnessed the film industry's appetite for remaking Broadway shows and then distributing them to millions of people all over the country, creating the new genre of film musicals in the late 1920s.

Fitzgerald uses allusions to plots and themes from musical theatre in his short stories, especially favouring those in which social-class boundaries are traversed in search of romance. Fitzgerald incorporates specific songs in his novels to allude to themes and plots of popular musicals of the day, which resonate within his texts. In terms of his short stories, Fitzgerald refers to popular songs from musical comedies in the theatre, but also to film musicals. This reflects his deep-seated interest in immersive media in which reader collaboration is key to ascertaining meanings in the texts, but many of these musical theatre references are lost on the modern reader.

Fitzgerald's allusions to musical theatre draw upon the profusion of collage-like interdisciplinary juxtapositions that have become known as the ‘collage aesthetic’. Prior to Jerome Kern and Oscar Hammerstein II's landmark production of Show Boat (1927), musical theatre very much relied on the aesthetic of vaudeville revues, without integration between song and action.