Rough-and-tumble play (RTP), also known as play fighting, is a common form of play frequently reported and studied by researchers. However, one important limitation of past research in the area of RTP has been the neglect of the adolescence period. Consequently, little is known about the function of adolescent RTP as well as about clinical characteristics of youth who engage in this activity after childhood. In a school-based sample of 1,771 middle school students (ages 9-16 years), the current study sought to address this gap by examining, via bivariate and multivariate logistic regression analyses, the potential cross-sectional associations of adolescent RTP with (a) selected demographic variables, (b) conduct problem symptoms, (c) substance use, and (d) risk-taking behaviors, including adjustment for several demographic confounders. Results indicated that adolescents reporting higher rates of conduct problem symptoms were more likely to report a recent participation in RTP. In addition, substance use (experimentation and current consumption of tobacco, alcohol, and marijuana) and risk behaviors assessed all were strongly associated with an increased likelihood of reporting an engagement in RTP. This finding suggests that participation in this activity probably implicates particular phenotypic characteristics including the propensity to engage in health-damaging behaviors. But the most profound issue raised by this research concerns the strong relationship between RTP and great levels of conduct disorder symptoms, suggesting a possible significant change in the functional significance of RTP in the adolescence period.