This study explored the current psychological characteristics and criminal behavior history of individuals who retrospectively reported being bullies, bully-victims, victims, or controls (i.e. neither victims nor bullies) during their last 2 years of high school. College students (n = 960) completed measures of criminal thinking, aggression, psychopathy, and criminal behavior online. We predicted bullies and bully-victims would demonstrate the highest scores for criminal thinking, proactive aggression, psychopathy, and have the most criminal infractions. Bullies and bully-victims had significantly higher scores on criminal thinking, aggression, psychopathy, and criminal behaviors than victims or controls. Additionally, men were significantly higher in criminal thinking, aggression, psychopathy, and had more criminal acts than women. There were no gender by bully group interactions. Logistic regression analyses differentiated bully-victims from bullies. Bully-victims tended to be male, higher in criminal thinking, and higher in reactive aggression. In addition, bully-victims were distinct from victims, showing higher criminal thinking and higher proactive aggression. Aggr. Behav. 37:145–160, 2011. © 2010 Wiley-Liss, Inc.