Shamans and artists have been perceived as similar across a variety of dimensions. Nonetheless, these similarities have not been systematically explored and are poorly understood. This study was designed to investigate these similarities. Stanley Krippner (personal communication, January 12, 2010) provided the initial definition of a shaman that, after minor modifications to more fully represent knowledge about shamans, became: A shaman is a socially designated spiritual practitioner who obtains information in ways not available to the shaman’s community through the voluntary regulation of the shaman’s own attention, which is used for the benefit of the shaman’s community and its members. Defining constructs were operationalized and validated cross-culturally to support multidirectional comparisons between artists and shamans using archival data from psychology, archaeology, anthropology, philosophy, art history, and creativity studies. Previous publications about 24 well-known artists provided archival data for comparisons with shamans. The dimensions explored included familial influence, talent, neurological functions, calling to vocation, social support, personality, training, initiation, inspiration, positive disintegration, transliminality, imaginal realms, altered states, purported psi experiences, mental health issues, soul retrieval, spiritual emergence, transpersonal orientation, intent to benefit, and creativity. Tables, charts, and diagrams organized archival information that, supported by descriptive comparisons, explored the nature and extent of similarities between artists and shamans. The integration of visual art, poetry, and stories provided an emic artist’s perspective and alternate ways of knowing for the reader. The study found that four artists from traditional cultures fulfilled all defining constructs of shaman, comprising a set of prototypical shamanic artists. In contrast, twenty artists fulfilled some, but not all, constructs defining shaman. These shamanlike artists were noncentral members in a fuzzy set where the shamanlike artists had family resemblances to traditional shamans and shamanic artists. The study identified and articulated gaps in knowledge as well as establishing a broad, well-grounded theoretical model that can serve as a foundation for future research on relationships between contemporary artists and shamans, and, potentially, contribute towards transformation of art experiences in artists, art audiences, and art institutions.