A cross-sectional study was conducted among 199 (104 urban, 95 rural) male students of classes VIII and IX, of two schools, in urban and rural areas of West Bengal to compare the prevalence of protective factors, mental health issues, and violence among the urban and rural adolescents using a self-administered questionnaire. Higher proportion of urban students than rural (67.3% vs. 62.5%) reported that their guardians understood their problems. Mental health issues like loneliness (17.3% vs. 9.8%), worry (17.3% vs. 10.7%), and suicidal thoughts (19.2% vs. 14.1%) were higher among urban students. Physical fight (53.8% vs. 11.6%), bullying (46.4% vs. 17%), physical attack by family members (46% vs. 17%), and by teachers (53% vs. 10.7%) were all more in urban adolescents. Mental health- and violence-related issues were prevalent more among urban students than those among rural students in spite of having more protective factors suggesting the need of frequent supervision, monitoring, and support of adolescents.