The author presents two clinical vignettes involving the deliberate use of humor by the analyst, which appeared to help foster an atmosphere that promoted the analytic process. It is suggested that the analyst's use of humor conveyed information about his mental state and his attitude toward the patient which disconfirmed inhibiting expectations and thus increased the patient's ability to be self-reflective and to face painful affects. The potentially deleterious effects of humorlessness in the analyst are also discussed.