Adolescent risk-taking can potentially result in serious individual and societal consequences. Previous research demonstrates that emotional and behavioral problems, particularly externalizing behaviors, are significantly associated with an array of risky behaviors such as substance use, sexual behavior, injury, and violence. However, the relationship between internalizing problems and risky behavior during adolescence remains unclear. Further, there is confusion surrounding comorbid internalizing and externalizing psychopathology and its relationship to risk-taking. Therefore, this study investigated the relationships between maladaptive risky behavior (i.e., smoking/tobacco use, alcohol use, marijuana use, sexual behaviors, and depression/suicidal behavior) and internalizing, externalizing, and comorbid behavioral symptoms. Participants included 476 high school students who met criteria for a large-scale intervention study due to emotional and behavioral difficulties. Analyses indicated that adolescents with comorbid symptomatology engaged in the highest rates of risky behavior. A significant interaction was found between behavioral symptoms and parent monitoring, indicating that students with internalizing problems and low levels of parent monitoring reported the highest levels of depression/suicidal behavior. Overall, internalizing dimensions of physical symptoms and somatic complaints had strong, positive associations with risky behavior, whereas social anxiety and harm avoidance had strong, but negative associations with risky behavior. Somatic complaints and separation anxiety both moderated the relationship between externalizing symptoms and suicidal behavior. Findings suggest that among adolescents with externalizing problems, high levels of co-occurring somatic complaints may decrease the risk of depression/suicidal behavior. Alternatively, high levels of separation anxiety may increase the risk of depression/suicidal behavior among adolescents with externalizing problems. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]