Popular culture richly impacted upon the literary aesthetics of Fitzgerald's short fiction. Whether in his groups of linked stories or in his discrete stories, there are several unifying features of a Fitzgeraldian story that help to create a self-referential space through which Fitzgerald can enact his self-parodic techniques. These unifying patterns include the conceits of disguise and mistaken identity, an unmistakably Fitzgeraldian tone of lyrical nostalgia, and the recourse to dance, music and film to explore what it means to be a modern American. Fitzgerald's short stories give us an insight into his response to modernity, as well as the intertextual dialogue that took place in the 1920s and 1930s between Fitzgerald's short stories and several other modernists’ attempts to confront modernity as manifested in popular culture.

Putting Fitzgerald's stories in the context of their foundations in early twentieth-century culture enables us to value them beyond their role in facilitating Fitzgerald's composition of novels. Fitzgerald's habitual ambiguity can be reread in the realm of parody: his interrogations of dominant cultural practices simultaneously risk endorsement or acquiescence through their faithful reproduction of their parodied targets. Fitzgerald's representations of popular cultural forms meet the criteria of what Linda Hutcheon coined in the late 1980s ‘complicitous critique’, and it is through these parodic portraits that Fitzgerald offers a more nuanced response to these cultural practices than is initially apparent. Fitzgerald deploys two modes of parody: he uses parodic plotting and characterisation (to make the formulae used for stories in the ‘slicks’ his own); and he also makes use of self-parody, both intentionally and subconsciously, often in an attempt to try to retain his audience, who had enjoyed his romantic stories of the early 1920s.

Ambiguity and parody are key features of African American cultural practices in the period between 1920 and 1940. It was during this same period that the Harlem Renaissance, in particular, was helping black writers, artists and performers find new subject matter that could speak to their early twentieth-century lives at the level of both form and content. Parody, satire and imitation were vital forces in the shaping of modernism, both white and black. Jazz music and dance celebrated imitative and improvisatory practices in radical new ways, and the aesthetics of repetition, ragging and variation are key elements of Fitzgerald's aesthetics, as shown by his subtle self-parody in portraying flapper figures.