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Two sides in Freud's attitude towards literature and art are presented: Freud the sensitive listener, whose interest in art is a potential springboard for a rich interdisciplinary dialogue; and Freud the conquistador, whose wish for power in ‘invaded’ territories is related to troublesome aspects of ‘pathography’ and ‘applied analysis’. The unique contribution of psychoanalysis may not be discovering objectively the true unconscious content of works of art, but rather enriching the exploration of the potential transitional space evolving between artist, work of art and readers or viewers, enhancing our sensitivity to multiple meanings and complex emotional influences of art. This requires exploring our own subjective experiences of art, which may be described as transferences (when art is mostly perceived as a source of insight) or countertransfererces (when artists and their work are basically experienced as troubled patients). Transference (broadly defined) and interpretation tend to intermingle, both in the clinical analytic encounter, and in any reading/viewing of art, be it by laymen, analysts or other scholars. Several examples from the psychoanalytic study of literature and film are given, and three pairs of contrasting interpretations are studied, concerning Kafka's The metamorphosis, Minghella's The English Patient and Polanski's Chinatown.