The article presents an interpretation of three narratives collected from three young professionals who volunteer as clowns for the young patients of a pediatric ward in a northern Italian hospital. Through their narratives, the clowns illustrate the role that imagination has in offering a different perspective on a given condition and context (in this case, illness and medical rules), and thereby in contributing to the strengthening of patient resources. The narratives, together with the notes from participant observation, trace the processes whereby the narrators came to identify with, and problematize, the characters of the whiteface clown and the Auguste type clown that the author first encountered during her fieldwork among Italian travelling entertainers, and then researched in the productions of artists (writers, musicians, painters, actors, and film directors).