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When it works well, the psychotherapeutic dialogue between therapist and patient can be creative, intuitive, ‘musical’. Drawing largely on Winnicott’s ideas, this paper describes the developmental process of ‘playing music’ as child psychotherapists, by describing what ‘musical’ inclinations look like in the psychotherapeutic work with patients, and how these inclinations can be fostered, in ourselves as well as in others (when in a teaching or supervisory role). Playing music in child psychotherapy has less to do with strictly adhering to psychoanalytic technique, and more to do with the therapist’s and patient’s ability to access internal freedom and creativity. In this paper, the author describes the internal and external dynamics that may facilitate or hinder the ‘musicality’ of child psychotherapists, focusing on the concept of the ‘analytic superego’ and issues of identity for today’s child psychotherapists. The author also acknowledges the complexity which derives from the increase in diversity in both psychoanalytic practitioners and patients, and the importance for the therapist to be a real object, as well as a transference object, by reflecting on and, where appropriate, addressing issues of sameness and difference in the therapeutic relationship.