Utilizing Jessor's Problem Behavior Theory as a theoretical foundation, 116 male and female students in grades 9-12 (mean age 16.8) from a Midwestern urban high school were surveyed to determine the prevalence and relationship among gambling behavior and parental and peer influences. To measure these variables, the following instruments were used: The SOGS-RA, the Inventory of Parent and Peer Attachment-Parent Scale, and The Alabama Parenting Questionnaire-Parental Monitoring and Supervision Scale. Almost all of the students (91%) reported gambling at least once in their lifetime while 36.2% reported gambling once a week, 19% reported gambling on a daily basis, and 26% were classified as problem gamblers (10% using the "narrow" SOGS-RA criteria). Parental gambling was related to levels of past year gambling as well as increased likelihood of being classified as a problem gambler. Increased parental attachment was also associated with decreased levels of adolescent gambling, while decreased parental trust and communication resulted in increased problem gambling. Measures of parental monitoring and supervision found similar outcomes in that increased monitoring and supervision resulted in lower levels of adolescent gambling. Additionally, when peer influences were moderated by parental influences, there was a moderating effect on gambling behavior. This study illuminates the continued importance parents play in both risk enhancing and risk inhibiting influences on adolescent participation in problem behaviors.