This study was designed to examine the relationship between hypermasculinity, stress, coping, smoking, and smoking-related behaviors and attitudes within a contextually-relevant, developmental model in male college students. 96 male participants were recruited from introductory psychology courses and participated in data collection. Results indicate that hypermasculine attitudes are related to the reported use of maladaptive coping skills, lower overall use of coping skills, increased levels of stress, smoking behavior and amount, and favorable perceptions of smokers. Hypermasculinity was found to moderate the relationship between smoking and stress. The presence of hypermasculine attitudes and favorable perceptions of smokers was found to accurately predict status as a smoker. Results are discussed in light of contributions to the current body of literature on men's health and smoking. Ideas for future research and implications for prevention and intervention programs are discussed