A significant challenge for animal care staff in zoos is the prevention or reduction of stereotypic behaviors in the animals they manage. Zoo professionals work to create opportunities for animals to demonstrate species-typical behaviors and to teach visitors about the natural behaviors of the animals on exhibit. Therefore the expression of stereotypic behavior presents a multi-disciplinary problem. Behavioral researchers have repeatedly examined stereotypic behavior in zoological settings to determine successful approaches to address this challenge. Three investigations of pacing in two adult male sloth bears (Melursus ursinus) at Smithsonian's National Zoological Park are presented here. In addition, a case report detailing observations of the rapid onset of an intense stereotypy in a young male sloth bear is included. The first study investigates the effects of five different enrichment strategies on pacing behavior in an adult male with a long history of pacing. The second is a two-year study examining seasonal changes and the effects of social companionship on pacing when the same adult male was housed with a breeding female, a non-breeding (contracepted) female, or a young male. In the third study, we present preliminary data on the effects of the selective serotonin re-uptake inhibitor, fluoxetine, as an adjunct pharmacological treatment for pacing. And finally, our case report details the development an intense stereotypy in a young male sloth bear just after he is weaned and separated from his mother. The findings reveal that the causes, degree, and effective management of even a single observed behavior such as pacing within even a single species can vary greatly by individual and circumstance, highlighting the need for individualized assessment and management plans.