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This article aims to compare one of Shakespeare’s late romances, The Winter’s Tale (1623), and Jean Rhys’ “Overture and Beginners Please,” (1976) the short story included in her last short fiction cycle, Sleep It Off Lady. Rhys’ short story depicts the protagonist Elsa’s participation in a school production of Shakespeare’s play and her performance as the vagabond character of Autolycus as a pivotal life-changing moment. Moreover, a parallel between Autolycus and Elsa is made at numerous moments, which ultimately creates intertexual images of alienation, transgression, and artistic aspirations. Yet “Overture and Beginners Please” has not been analyzed in conjunction with Shakespeare. In turn, by juxtaposing The Winter’s Tale and “Overture and Beginners Please,” this article looks at how the figure of Autolycus allows Shakespeare and Rhys to construct and present their own winter’s tales. In the process, both texts remind us of the power of artistry, which can be dangerously deceptive but at the same time provides unexpected and genuinely meaningful opportunities.