Young men who have sex with men (YMSM) have higher rates of cigarette smoking than their heterosexual counterparts, yet few studies have examined factors associated with cigarette smoking among YMSM. The present study sought to understand how different types of gay community connection (i.e., gay community identification and involvement, gay bar/club attendance) were associated with smoking among YMSM recruited through venue-based sampling in Los Angeles, California (N = 526). Structural equation modeling was used to isolate direct and indirect effects of gay community connection on smoking through cognitive and psychological mediators (i.e., psychological distress, health values, internalized homophobia). Findings indicate YMSM cigarette smoking prevention and intervention must be tailored to address the direct and indirect influences of the gay community.