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Bullying and victimization occurring in adolescence can have a long-lasting negative impact into adulthood. This study investigates whether conduct problems (CP) and dimensions of psychopathy predict the developmental course of bullying and victimization from ages 12 to 14 among 1,416 Greek-Cypriot adolescents. Results indicate that initial levels of bullying were highest among adolescents scoring high on narcissism, impulsivity, or CP—particularly for those also showing high callous-unemotional (CU) traits. Bullying behaviors were also more stable among youth scoring high on narcissism. Further, youth high on impulsivity showed more stable victimization by peers across development. Importantly, adolescents high on CP+CU were at greater risk for engaging in bullying across development compared with those scoring lower on CU traits or CP.