OBJECTIVE To examine the associations between a self-reported history of gambling or problems related to gambling and health risk behaviors in adolescence. METHODS An anonymous risk behavior survey was administered to 21 297 8th- through 12th-grade students in 79 public and private schools in Vermont. Gambling or problems related to gambling were the outcome variables of interest. Demographic variables and 13 target risk behaviors related to substance use, sexual activity, and violence were tested for association with gambling and problems related to gambling. RESULTS Of the students, 53% reported gambling in the past 12 months, and 7% reported problems attributable to gambling. Male gender, any use of alcohol, infrequent use of cigarette smoking, any marijuana use, any inhalant use, infrequent steroid use, frequent illegal drug use, seatbelt nonuse, driving after drinking alcohol, being threatened, carrying a weapon, being involved in a fight, and years of sexual activity were all significantly associated with reported gambling in the past 12 months. Among the students who gambled, younger age, male gender, daily marijuana use, frequent use of cocaine, frequent use of inhalants, any steroid use, never wearing seatbelts, carrying a weapon for up to 3 days a month, fighting, and years of sexual activity were all significantly associated with reported problems with family and friends as a consequence of gambling. There was an increase in the absolute number of risk behaviors reported between those who had not gambled, those who had gambled, and those for whom gambling had created problems. CONCLUSIONS Risk behaviors are associated with gambling in adolescence. The typology of risk behaviors was different for adolescents who reported gambling compared with those for whom gambling had created problems. Both gambling and problems related to gambling were significantly associated with the absolute number of risk behaviors reported by adolescents in a graded manner. Involvement in gambling should be assessed as part of the health encounter. Assessment may provide a nonthreatening entry into the evaluation of other risk behaviors. Furthermore, it may identify youth who are at risk of developing additional risk behaviors or pathological gambling. Interventions then could be targeted toward prevention of these undesirable outcomes.