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This paper describes three psychoanalytic perspectives each of which represent central elements of psychoanalysis' past, present and future through the literary metaphors of Sherlock Holmes, Sir Lancelot and the Wizard of Oz. These metaphors provide a way of understanding the evolving nature of psychoanalytic theory and practice. Sherlock Holmes represents a nineteenth century search for hidden truths, Sir Lancelot represents contemporary approaches which emphasize new relational experiences and the Wizard of Oz represents the emerging transformational models in psychoanalysis which emphasize the creation of subjective meaning. Transformational models are emerging in psychoanalysis, developmental psychology and neuropsychology; each emphasizes multiple modes of apprehending the world and the development of the capacity for symbolization and the creation of subjective meaning. A transformational model of psychoanalysis is described and the process of progressive symbolization is illustrated with four moments from an extended psychoanalytic treatment. Additional clinical material is used to illustrate the three psychoanalytic approaches.