This study examined cyberbullying among adolescents across United States and Singapore samples. Specifically, the purpose of the investigation was to study the differential associations between proactive and reactive aggression, and cyberbullying across two cultures. A total of 425 adolescents from the United States (M age = 13 years) and a total of 332 adolescents from Singapore (M age = 14.2 years) participated in the study. Results of the moderator analyses suggested that nationality was not a moderator of the relationship between proactive aggression and cyberbullying, and between reactive aggression and cyberbullying. As expected, findings showed proactive aggression to be positively associated with cyberbullying, after controlling for reactive aggression, across both samples. Likewise, as hypothesized, reactive aggression and cyberbullying was not found to be significant after controlling for proactive aggression across both samples. Implications of these findings were discussed: (a) Proactive aggression is a possible risk factor for both bullying and cyberbullying; (b) proactive and reactive aggression could be argued to be distinct as they have different correlates—only proactive aggression contributed to cyberbullying after controlling for reactive aggression; (c) this research extends previous work and contributes toward cross-cultural work using similar and comparable measures across different samples; and (d) prevention and intervention programs targeted at proactive aggressive adolescents could adopt a two-pronged approach by changing mind sets, and by understanding and adopting a set of rules for Internet etiquette.