To clarify reasons for drinking in relation to problem drinking behavior, 494 male students, aged 15 to 18 years old and attending high schools in Tokyo, Japan, were examined by self-rating questionnaires including the Kurihama Alcoholism Screening Test (KAST). Three hundred and forty-two students (69%) completed the questionnaires, of whom 143 indicated that they were current drinkers of alcohol (42% of respondents). Of the 143, 16 (11%) reported, through the KAST, experience of problem drinking behavior. A factor analysis of 36 reasons for drinking identified 5 factors: Escapism, Sociability, Tension Reduction, Acting Like a Man, and Enjoyment/Home. A logistic regression analysis showed that drinking because of Escapism, Sociability, and Tension Reduction was significantly related to problem drinking behavior. Also, there was significant correlation between the 3 factors and the number of KAST items experienced by the 143 respondents. Our findings suggest that the factors of Escapism, Sociability, and Tension Reduction lead to problem drinking in Japanese high school students.