For the past 50 years, significant gaps have existed in gender and racial diversity across various medical specialties, despite the many benefits of a diverse physician workforce. One proposed approach to increasing diversity is top-down diversification, in which diverse leadership results in increased minority and female workforce representation. To investigate the changes in academic medical leadership diversity from 2007 to 2019 and to assess the recent leadership diversity of various specialties compared with the averages across all specialties. This was a cross-sectional analysis of physicians in varying academic roles in 2007, 2019, and 2020. Demographic data were collected via specialized reports from the Association of American Medical Colleges. Included were 4 primary care specialties (internal medicine, family medicine, pediatrics, obstetrics/gynecology [OB/GYN] and 4 surgical specialties (orthopedic surgery, neurologic surgery, otolaryngology [ENT], general surgery). Study participants were faculty, program directors, and chairpersons. Data were analyzed for the years 2007, 2019, and 2020. Self-reporting of demographic information to residency programs collected via the Graduate Medical Education Track Survey. Proportions of each race/ethnicity and sex among cohorts of participants and comparisons between them. The total number of individuals investigated included 186 210 faculty from 2019 (79 441 female [42.7%]), 6417 program directors from 2020 (2392 female [37.3%]), 1016 chairpersons from 2007 (89 female [8.8%]), and 2424 chairpersons from 2019 (435 female [17.9%]). When comparing chairperson diversity from 2007 to 2019, only internal medicine and general surgery experienced significant increases in minority (aggregate category used throughout the investigation to refer to anyone who self-identified as anything other than non-Hispanic White) representation (90% increase [11.7 percentage points, from 13.0% in 2007 to 24.7% in 2019]; P = .01 and 96% increase [13.0 percentage points, from 13.5% in 2007 to 26.5% in 2019]; P < .001), respectively; meanwhile, several specialties saw significant increases in female representation during this period (family medicine by 107.4%, P =.002; pediatrics by 83.1%, P =.006; OB/GYN by 53.2%, P =.045; orthopedic surgery by +4.1 percentage points, P =.04; general surgery by 226.9%, P =.005). In general, surgical specialties had lower leadership diversity than the average diversity of all residency programs, whereas primary care specialties had similar or increased diversity. Study results suggest that some specialties have made significant contributions toward bridging diversity gaps whereas others continue to lag behind. Our recommendations to improve academic medical leadership diversity include programs and institutions (1) publishing efforts and outcomes of diversity representation, (2) incorporating a representative demographic for leadership selection committees, and (3) actively promoting the importance of diversity throughout the selection process.