The pursuit of unhealthy behaviors, such as smoking or binge drinking, not only carries various downside risks, but also provides pleasure. A parsimonious model, used in the literature to explain the decision to pursue an unhealthy activity, represents that decision as a tradeoff between risks and benefits. We build on this literature by surveying a rural population in South Africa to elicit the perceived riskiness and the perceived pleasure for various risky activities and to examine how these perceptions relate to the pursuit of four specific unhealthy behaviors: frequent smoking, problem drinking, seatbelt nonuse, and risky sex. We show that perceived pleasure is a significant predictor for three of the behaviors and that perceived riskiness is a significant predictor for two of them. We also show that the correlation between the riskiness rating and behavior is significantly different from the correlation between the pleasure rating and behavior for three of the four behaviors. Finally, we show that the effect of pleasure is significantly greater than the effect of riskiness in determining drinking and risky sex, while the effects of pleasure and riskiness are not different from each other in determining smoking and seatbelt nonuse. We discuss how our findings can be used to inform the design of health promotion strategies.