Using survey results from the 1998 Twin Cities Lesbian, Gay, Bisexual, and Transgender (LGBT) Pride Festival (N = 535), we explored associations between body image and unsafe anal intercourse (UAI) among men who have sex with men (MSM), and evaluated whether body satisfaction mediated this association. MSM who reported underweight body image had lower odds than those who reported average weight of UAI (AOR = 0.33; 95% CI = 0.13, 0.85); body satisfaction was not found to mediate this association. 13.3% of men who reported overweight/obese body image had engaged in UAI compared with 21.6% of those who reported average weight and 8.2% of those who reported underweight (p < .05). Compared with MSM in exclusive relationships, MSM in non exclusive relationships had increased odds of UAI (AOR = 5.78; 95% CI = 2.96, 11.29) as did men who were not partnered (AOR = 3.20; 95% CI = 1.72, 5.93). These findings highlight the importance of including body image in sexual behavior models of MSM to better understand body image's role in influencing sexual risk and sexually transmitted infections (STI)/human immunodeficiency virus (HIV) transmission.