Abstract Given the potential for media portrayals to affect adolescents’ cognitions regarding risk behaviors and the importance of message interpretation processes, this study investigates how adolescents give meaning to media portrayals of risk behavior (e.g., alcohol, smoking, drugs, sex, and reckless behavior) and which factors play a role within this process through 7 focus groups followed by 50 individual interviews with adolescents. Findings indicate adolescents are far from passive consumers of media portrayals of risk behavior. Participants expressed awareness of the ubiquity and symbolism with which risk behaviors are portrayed in popular media and were mostly adept at deconstructing the images portrayed. However, this did not always translate to critical responses. An interplay of real-life experiences and message characteristics informed judgments about media portrayals of risk behavior. Contributing factors to critical and media-literate deconstructions are distilled in the form of barriers and boosters, and suggestions for media literacy interventions are formulated.