Longitudinal models of the development of adolescent smoking and smokeless tobacco (ST) use were tested for a sample of 643 adolescents, age 14 to 17. The sample was assessed at three time points. Smoking, smokeless tobacco, and other problem behaviors formed a single problem behavior factor. Structural equation modeling indicated that inadequate parental monitoring and association with deviant peers at Time 2 predicted tobacco use at Time 3. When parental and peer smoking at Time 2 were added to the model, each accounted for significant variance in predicting Time 3 smoking, but inadequate parental monitoring and association with deviant peers still accounted for some of the variance in Time 3 smoking. In predicting boys' smokeless tobacco use, monitoring at Time 2 predicted smokeless tobacco use, but only when parental approval of ST use was not included. Fathers approval of ST use at Time 2 predicted ST use at Time 3, while maternal disapproval predicted its use.