Archaic narcissism, grandiosity, and entitlement, as well as narcissistic rage—through favourable developmental circumstances or through analysis—can be transformed into creativity, humour, empathy, and wisdom (Kohut, 1966). Among the resources required of the analyst to co-construct such transformations with the patient in the analytic setting are humour and spontaneity—variants of creativity. Through these resources an incomparable degree of intimacy between patient and analyst can be achieved. Providing such an ambience of safety can enable a patient to access and explore guilt- and shame-ridden experiences and transference fantasies that are often difficult and painful to reveal. Two clinical illustrations are presented in which play and humour were embedded in the ongoing analytic process. Both the value and timing of such interventions, their relation to the analyst's exhibitionism, as well as the value in refraining from making such interventions are discussed.