Background: Among U.S. medical school deans, there is a wide gender gap, most prominent at the highest levels. We aimed to discover how well women physicians were represented within the pool of women deans compared with the pool of men deans. Materials and Methods: A cross-sectional study was performed on 149 allopathic medical schools in the United States. For each school, information was collected on deans' names, titles, genders, and degree(s). Chi-square analyses were performed to determine association between gender and dean ranks. Results: Of the 2559 deans included from 149 medical schools, 1649 (64.4%) were physicians, and of these, women physicians accounted for 634 (38.4%), a significant under-representation (p < 0.00001). In comparison, the 626 nonphysician doctorate-holders of which women accounted for 291 (46.5%, p = 0.061) were equally represented. Of the 284 deans with bachelor's or master's degrees, women accounted for 180 (63.4%), a significant over-representation (p < 0.00001). This difference was most profound at the lower tier (assistant) dean level. A lower tier physician dean was 1.25 times more likely to be a man than a woman, and a higher tier (dean of medical school, senior associate, vice, or associate) physician dean was 1.16 times more likely to be a man. Conclusions: Women physicians were under-represented among medical school deans compared with men. This disparity held among lower tier and higher tier deans.