Oscar Wilde was described by W. B. Yeats as "a man of action, a born dramatist." Although people did not recognize him as a serious playwright until the 1890s, Wilde had managed to find other outlets for his theatrical passion, for example in writing fiction. In this paper, it is argued that Wilde incorporates metadrama into his 1888 fairy tale collection, "The Happy Prince and Other Tales." The discussion focuses on how Wilde employs the metatheatrical devices of the-play-within-the-play and role-playing to treat the social problems of self-immolating altruism and identity crisis respectively. In representing the social malady of exaggerated self-sacrifice, Wilde adopts the satirizing strategy which maintains the sense of the illusion evoked by the inset tale while simultaneously estranging the outer/inner story connection by dint of nonrecognition. Similarly, identity crisis is reflected through an estranged mode of role-playing: Wilde's characters impress the reader as performing too much to have a real-life identity. The ironic detachment enabled by the two metadramatic tactics in question constructs a mask, which allows Wilde to criticize social problems in a non-imitative manner, the central aim of the 1888 volume. In Wilde's fairy tales, the use of metadrama, in facilitating representations from a critical distance, can be seen as an example of what is labelled as "sincere mannerisms." Beneath the mask of his insincerity, Wilde is truly a serious humanist, assiduous in imparting to us the knowledge of ourselves and our existential condition.