Substance use such as tobacco is common during the adolescent stage of development. Nicotine, the primary psychoactive compound in tobacco, is considered to be one of the most addictive drugs. Cigarette use has been associated with a wide range of health complications and is listed as one of the most preventable causes of disease in the United States with 480,000 smoking-related deaths per year. Those who use substances during adolescence are more likely to develop tobacco and other substance use disorders later in life. Further research on the underlying factors that predict cigarette use could support the development of new evidence-based preventative treatment interventions. The goal of this study was to investigate the relationship between executive dysfunction measured by the Behavioral Rating Inventory of Executive Functions (BRIEF-2), distant parental relationships including parental support, monitoring, decision influence, and communication; and cigarette use two years later. The subjects (n = 503; ages 12 through 18) were all participants in the National Consortium on Alcohol and Neurodevelopment in Adolescents (NCANDA) study. To explore these interactions, specific paths were tested in a multivariate longitudinal mediation analysis to measure both latent (executive functions and parental support) and observed (cigarette use in the past 365 days) variables. A confirmatory factor analysis was used to construct the latent variables and bivariate and multivariate models were used to assess these interactions further. The results indicated that distant parental relationships and executive dysfunction predicted cigarette use in adolescent populations two years later. Distant parental relationships were also found to predict executive dysfunction and as expected both parental relationships and executive dysfunction acted as partial mediators. Although, the modest reduction in the relationship between parental relationships, executive functions, and cigarette use suggests the mediation hypotheses may not be 3 EXECUTIVE FUNCTIONS, RELATIONSHIPS, AND CIGARETTES truly be supported. Age and sex were found to be even greater predictors of cigarette use. Furthermore, significant sex differences were reported; the average female in the model had a (4.9%) probability of being a cigarette smoker, while an average male had a (9.7%) probability, future studies should explore these interactions further. Preventative treatment interventions should aim to close the distance in a child-parental relationship by improving levels of parental support, actual monitoring, decision influence, and communication, which is also effective at reducing internalizing and externalizing behaviors associated with executive dysfunction and substance use. However, past research has shown social economic status may influence both executive functions and parental relationships. Adolescents who express characteristics of executive dysfunction, especially those who are closer to 18 years old and have distant parental relationships, should be a targ...