Humor exists in workplaces in many forms and it is purposefully used by a variety of types of workers. It is rarely neutral in the workplace, often it is used by workers or supervisors as means to an end. Although humor is pervasive in the workplace, it has received scant attention in the HRD literature. In particular, connections are rarely made between the rich literature base of humor and the practices of HRD in work settings. This chapter offers a discussion between an HRD professional who has a great passion for connecting HRD theory and practice, and a university professor who has a passion for examining humor in the workplace. Given that they each share a questionable sense of humor, the intent of the chapter will be to use forms of humor to provoke new insights about humor applications in the workplace, and to foster scholarship that links HRD practice and humor literature.