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The author attempts to apply the psychoanalytic concept of “prolonged adolescence” to two literary works, both of which are embedded in England's postwar social and political climate. The discussion of John Wain's Hurry on Down ([1953] 1979) and John Osborne's Look Back in Anger ([1956] 1989), by necessity, involves a look at those factors responsible for shaping the cultural “mood” in those days. However, the author's primary concern lies with how two particular (fictional) individuals, or antiheroes, deal with the frustration, which, although generally felt among contemporary academia, in their cases seems to hide a much deeper layer of mental insecurity and instability. In fact, we come to feel that the characters have not achieved a proper sense of identity (“self”) and are, from the point of view of maturity, delayed and, hence, “unfitted” to cope adequately with the external world. Having long achieved formal adulthood, they seem to have gotten “stuck” somewhere along the passage of growing up. Essential papers by Sigmund Freud and his daughter Anna, as well as a very early paper on the topic by Siegfried Bernfeld, are, among others, taken into account, as is the profound research done by Peter Blos on the subject in question.