In this interview, Dr. Arnie Cann discusses his research and views on the ubiquitous role of humor in psychological health and well-being. The interview begins with Professor Cann recounting how he originally became interested in studying humor. He then reflects on the main findings associated with the wide variety of humor-related studies he has conducted over the years. In doing so, Dr. Cann provides suggestions and ideas for further research investigating the role of humor in health and well-being. Specific topic areas discussed include the use of humor in the workplace and other social domains, personality approaches to humor, humor and interpersonal processes, humor and psychopathology, and humor’s role in dealing with stress and well-being. One of the prominent themes in this interview is the clear recognition of sense of humor as a multi-dimensional construct that includes various components that may either be beneficial or detrimental to well-being. A further important theme is the major distinction between humor as an inherent personality construct versus humor that results from exposure to stimuli (e.g., a comedy film). Comments are also provided by Dr. Cann on how the positive affect stemming from humor may be of particular benefit to the individual. Also discussed is the recent move to more fully integrate contemporary humor research with positive psychology approaches. The interview concludes with Dr. Cann providing several recommendations regarding future theorizing and research on the role of humor in psychological well-being.