This paper discusses current perspectives on play and leisure and proposes that if play and leisure are to be accepted as viable occupations, then (a) valid and reliable measures of play must be developed, (b) interventions must be examined for inclusion of the elements of play, and (c) the promotion of play and leisure must be an explicit goal of occupational therapy intervention. Existing tools used by occupational therapists to assess clients’ play and leisure are evaluated for the aspects of play and leisure they address and the aspects they fail to address. An argument is presented for the need for an assessment of playfulness, rather than of play or leisure activities. A preliminary model for the development of such an assessment is proposed.