This study explored humor production and communicator style within the dyadic communicative relationship between organizational managers and subordinates. Research questions considered positive, expressive, and negative humor functions and manager-subordinate relational style, communication style, sex, and dyad characteristics. Results indicated that both organizational managers and subordinates report using conversational humor, mostly positive and expressive humor. Results also indicate communicator image, dominant or affiliative communication style, and sex are related to the type of conversational humor initiated by organizational managers and subordinates. It appears that organizational power/dominance and sex are better predictors of humor usage than other characteristics. Overall, results suggest that relational factors, such as one's humor, may be important to the enactment of organizational citizenship behaviors among subordinates.