Alcohol use among adolescents is a health-risk behavior that can result in serious consequences. Furthermore, adolescents participate in drinking games—a risky drinking behavior designed to facilitate heavy alcohol consumption in a short period of time. Both alcohol expectancies and drinking motives have been identified as robust correlates of alcohol consumption during adolescence. The present study examines the direct and indirect effects of alcohol expectancies on hazardous alcohol use and frequency of drinking game participation. Participants (n = 254) were local high school students who reported alcohol use in the past month. Structural equation models showed that both positive expectancy outcomes and valuations were directly associated with hazardous alcohol use. Moreover, enhancement motives significantly mediated the associations between positive expectancy outcomes and hazardous alcohol use. Finally, social motives mediated the associations of both positive expectancy outcomes and valuations with frequency of drinking games participation and with hazardous alcohol use. Implications for intervention and prevention programs are discussed.