Risky sexual behaviors among adolescents can increase adverse outcomes including unplanned pregnancy or contraction or transmission of disease. Adolescents who engage in risky sexual activities are at increased risk for adverse health and social outcomes compared to those who do not engage. Despite declines in adolescent pregnancy and birth rates, the diagnosis of sexually transmitted infections (STIs) is steadily increasing among adolescents. Moreover, African American adolescent boys in the United States, specifically in the southeastern region are disproportionally at greater risk for STIs, and STI diagnosis within this population has increased over time, compared to their white counterparts. This study sought to identify factors associated with condom use among adolescent boys in the Deep South. Using data from the Mobile Youth Survey, a longitudinal adolescent community-based survey, this study assessed the relationship between personal, behavioral, and environmental factors and condom use among African American adolescent boys (14–19 years). Younger participants (14–15 and 16–17) were more likely to use a condom during the last sexual intercourse compared to older participants (18–19 years). High positive attachment to boy/girlfriend was associated with increased condom use. The number of sexual partners, age at their first sexual encounter, recent sexual behavior, and having an STI were also associated with increased condom use among participants. The study provides further insights into factors associated with condom use among African American adolescent boys and results can inform the development of sexual health interventions.