The current study investigated (a) the relationship between self-esteem and health-risk behaviors and use of cigarettes, alcohol, and drugs, and (b) the gender differences in self-esteem and health-risk behaviors among a group of 243 late adolescents (124 males, 119 females) using a cross-sectional survey design. The age range of the participants was 17 to 24 with a mean age of 20.43 (SD = 1.21). Participants completed the Rosenberg Self-Esteem Scale and a self-report questionnaire including items about demographic characteristics and participation within a range of health-risk behaviors. The findings of the study revealed that self-esteem was negatively associated with alcohol and illicit drug use; however, these results did not suggest any significant relationship between self-esteem and smoking cigarettes. Comparisons between males and females did not indicate any gender differences on the self-esteem scale. On the other hand, significant gender differences were found on cigarette and drug use with males reporting more cigarette and drug use. Limitations of the study and possible implications for counseling practice are discussed.