This study explored the roles of gender and self-esteem in the relations between various teasing experiences and externalizing behavior. Externalizing behavior was measured as reported risk-taking and alcohol consumption. Within a sample of 651 high school students located in the Midwest, males reported significantly more externalizing behavior and higher self-esteem than females. Males and females significantly differed in several associations between teasing experiences and externalizing behavior. Only females experienced self-esteem as a mediator of these relations. This study significantly contributes to existing literature by illuminating many unique and unexpected relations between teasing, self-esteem, and externalizing behavior. The findings may assist clinicians and educators by providing improved methods of detection, intervention, and prevention of the potentially harmful effects of teasing.