This article presents data regarding the prevalence of trying smokeless tobacco in a longitudinal sample of 2,714 urban, ethnically diverse adolescent males and females. A predominance of trial use was found in white males in 8th and 9th grades. Also presented is the relation of smokeless tobacco onset to experimentation with other drugs (cigarettes, alcohol, marijuana), cigarette smoking in significant others, self-image as a smoker, risk taking, and smoking refusal self-efficacy. Smokeless tobacco onset was related to higher levels of cigarette smoking and lower quit rates, and was positively associated with use of cigarettes by significant others, one's self-image as a smoker, and with a disinclination to refuse cigarette offers. Finally, onset was more probable in individuals who had previously tried alcoholic beverages and marijuana, and who reported enjoying taking risks. A multivariate logistic regression analysis retained sex, smoking level, beer and wine use, and risk taking as predictors of smokeless tobacco onset. Apparently, smokeless tobacco is an additional activity in which drug-experimenting male adolescents are likely to participate.