Robust research shows that poor parenting practices are related to adverse outcomes among adolescents; however, few have examined the interaction between parenting variables and adolescent outcomes within the context of exposure to relentless crime. The current study examined the combined effects of parental monitoring and discipline on marijuana involvement and deviant peer affiliation among adolescent males living in Los Angeles neighborhoods with concentrated crime. For this study, areas with higher-than-average crime rates were selected based on census data, published statistics, and law-enforcement data. The study included 349 males between 13 and 17 years of age, mostly Latino (70.2%) and African American (28.4%). Data were collected using questionnaires to interview participants and analyzed using logistic regression. Results suggest that among adolescent males in geographic areas of high violence and crime, the interaction between parental monitoring and discipline was significantly related to marijuana involvement and deviant peer affiliation. Follow-up analyses showed parental monitoring was only an effective tool at higher levels of consistent parental discipline. In the absence of consistent discipline, good parental monitoring was ineffective at preventing marijuana involvement and affiliation with deviant peers. Results suggest that if time and resources are limited, clinicians should consider focusing on the use of consistent discipline with parents residing in high-crime neighborhoods.