We examine the experience of boredom and its relationship to troublemaking and drug use among rural youth in southwestern New Mexico. We draw on qualitative research with area youth to describe what they think about drug use and how they situate it within their social circumstances. We then locate youth drug use within globalized processes affecting this setting, including a local economic environment with limited educational and employment opportunities for youth. Drug use emerges as a common social practice that enables youth to ameliorate boredom, yet only some youth become known as troublemakers. Study findings offer insight into how dominant social institutions—schools and juvenile justice authorities—shape the construction of trouble from the perspectives of youth. We contend that boredom and troublemaking among rural youth are not simply age-appropriate forms of self-expression but instead represent manifestations of social position, political economic realities, and assessments of possible futures.