BACKGROUND: For 2 decades, women have made up nearly half of medical school graduates, yet this has not translated to equity in promotion. We compare historical trends in the academic career pipeline among 4 specialties by sex. METHODS: Using the Association of American Medical Colleges database, faculty sex and rank were examined in oncology, gastroenterology, cardiovascular medicine, and general surgery for the years 2000 and 2020. RESULTS: Cardiovascular medicine, gastroenterology, and general surgery all had similar lower representation of women faculty in 2000 (17%, 17%, and 15%, respectively) compared with oncology (26%). Cardiovascular medicine and general surgery have seen smaller increases in representation over the last 20 years compared with gastroenterology and oncology. Oncology and gastroenterology are projected to reach sex parity in 2024 and 2029, followed by general surgery in 2054. At the current rate, cardiovascular medicine will not reach sex parity until 2070. CONCLUSION: Oncology and gastroenterology, compared with cardiovascular medicine and general surgery, have seen larger gains in representation of women over the past 2 decades, including at Professor rank. Disparities persist in specific fields; lessons may be learned from other specialties in which women are more likely to be promoted to leadership positions.