Recent media attention has increased interest in behavioral, mental health, and academic correlates of involvement in bullying. Yet, there has not been much interest in investigating the co-occurrence of other health-risk behaviors, such as gang membership, weapon carrying, and substance use. The potential influence of contextual factors, such as youth ethnicity, urbanicity, and school characteristics, also has been overlooked in previous research. The current study examined different subtypes of involvement in bullying--as primarily a victim, as primarily a bully, as both a victim and bully, and no involvement--and the association with significant health-risk behaviors, including engaging in violence and substance use, as well as academic problems. The analyses use self-report data from 16,302 adolescents (50.3% female, 62.2% Caucasian, 37.8% African American) enrolled in 52 high schools. A series of three-level HLM analyses revealed that bullies and bully/victims were generally at greatest of risk of being involved in violence, engaging in multiple types of substance use, and having academic problems. These findings extend prior research by emphasizing a potential link between involvement in bullying and multiple health-risk behaviors, particularly among urban and African American high school youth.