The purpose of this study was to examine whether a relationship exists between parenting styles, adolescent self-esteem, and health risk behaviors. The sample consisted of 343 middle school students from Harrisonburg, Virginia who completed a questionnaire consisting of three major components: parenting styles, self-esteem, and health risk behaviors. The health risk behaviors component contained questions concerning alcohol use, drug use, sexual activity, and eating behaviors. The parenting styles section of the questionnaire classified the participants into one of four types of parenting styles: authoritarian, authoritative, permissive, and neglectful. The Rosenberg Self-Esteem scale divided the participants into one of three levels of self esteem: low, average, and high. The risky behaviors component of the questionnaire classified the participants as being low risk-takers, experimenters, or high risk-takers, with the exception of the eating behaviors component, which classified participants as being either high or low risk takers. In general, no relationship was found between parenting styles, self-esteem, and health risk behaviors.