(1) Background: The study aims to assess cigarette smoking and waterpipe experimentation among Lebanese adolescent school students with respect to their gender, region, age, and socioeconomic status. (2) Methods: This is a cross-sectional study, where students between 11 to 18 years of age were included from all over Lebanon. (3) Results: A total of 1133 students were interviewed. The total proportion of adolescents who ever experimented with cigarette smoking was 24.5%. Males experimented with cigarette smoking more commonly than females (31.9% vs. 19.1%; p < 0.001). Cigarette smoking experimentation was higher among students from the Beirut area (33.6%; p < 0.001) in comparison to other regions, and among those with poor health perception (29.1% vs. 19.8%; p < 0.001) compared to students with excellent health perception. The total proportion of adolescents who ever used a waterpipe was 33.9%. Waterpipes were significantly more experimented with among males than females (40.3% vs. 29.8%; p < 0.001), and among students with bad perception about their health (39.4% vs. 28.9%; p < 0.001). Adolescents who experimented with both cigarettes and waterpipes constitute 22.2% of the studied sample. (4) Conclusions: The rate of tobacco product use is alarming and constitutes a major public health issue for adolescents that urgently needs intervention. The findings raise important policy implications for the development of cigarette smoking prevention programs for youth.