This paper illustrates a ‘Conversational Model’ of art therapy. The Conversational Model was jointly created by Robert Hobson and Russell Meares. It is a developmental theory unique in its clinical application. The focus of the paper is two sessions that altered the course of therapy. In these sessions, variations on Donald Winnicott's “squiggle‐game” and Hobson's “party game” were used to engage an isolative, reluctant incarcerated patient. The interventions illustrate the basic tenets of the Conversational Model. The theoretical process – from disruption to repair – is visually recorded in the artwork. The central argument of the paper is that interactive art therapy interventions can be effective, when used appropriately. By engaging the patient in a ‘visual’ conversation, he/she may develop an emotional vocabulary, a prerequisite for a psychotherapeutic conversation. The paper begins with a brief historical overview of the interface between art and psychoanalysis, the context out of which ‘art therapy’ – a distinct body of theory – evolved. Theory interweaves with clinical material in a narrative style.