Objective: Black youth continue to experience persistent sexual health disparities that can adversely impact their lives. There is a dearth of research examining adolescent sexual health and the role of perceived life chances and leisure activities. Methods: This study uses data from Wave 3 of the Birmingham Youth Violence Study (BYVS) to explore these variables among urban Black youth (N = 404). Results: Key findings support the role of certain leisure activities and improved life chances with regard to sexual risk behaviors. Greater time in social leisure activities was associated with earlier sexual initiation and more sexual partners whereas academic and media leisure activities were linked to delayed sexual initiation. Conclusion: This study underscores the importance of leisure activities in prevention and intervention approaches for urban youth.