In this paper, the 1998 film The Truman Show is considered as a parable about parenting, adolescence, and patients’ struggle to break free of defensive structures. The central conceit of the film is that Truman lives in a world entirely created by, and under the control of the show's director, Christof, with all the other characters in his life being actors playing semi-scripted parts. The paper explores how this resonates with the problems faced by all parents when it comes to allowing their children freedom to develop independently and to face the realities of life; the difficulties faced by all adolescents leaving latency behind to encounter themselves more fully; and the therapeutic task with all patients of relinquishing the relative safety created by symptoms and projective mechanisms.