Incarceration has been proposed to be a driving factor in the disproportionate impact of HIV in African-American communities. However, few data have been reported on disparities in criminal justice involvement by race among men who have sex with men (MSM). To describe history of arrest and associated factors among, we used data from CDC's National HIV Behavioral Surveillance system. Respondents were recruited by time-space sampling in venues frequented by MSM in 15 US cities from 2003 to 2005. Data on recent arrest (in the 12 months before the interview), risk behaviors, and demographic information were collected by face-to-face interview for MSM who did not report being HIV-positive. Six hundred seventy-nine (6.8%) of 10,030 respondents reported recent arrest. Compared with white MSM, black MSM were more likely to report recent arrest history (odds ratio (OR), 1.6; 95% confidence interval (CI), 1.3-2.1). Men who were less gay-identified (bisexual [OR, 1.5; 95% CI, 1.1-1.9] or heterosexual [OR, 2.0; 95% CI, 1.2-3.5]) were more likely to report recent arrest than homosexually identified men. In addition, men who reported arrest history were more likely to have used non-injection (OR, 3.0; 95% CI, 2.4-3.6) and injection (OR, 4.7; 95%, 3.3-6.7) drugs, exchanged sex (OR, 2.7; 95% CI, 2.1-3.4), and had a female partner (OR, 1.5; 95% CI, 1.2-2.0) in the 12 months before interview. Recent arrest was associated with insertive unprotected anal intercourse in the 12 months before interview (OR, 1.4; 95% CI, 1.2-1.7). Racial differences in arrest seen in the general US population are also present among MSM, and history of arrest was associated with high-risk sex. Future research and interventions should focus on clarifying the relationship between criminal justice involvement and sexual risk among MSM, particularly black MSM.