Despite a growing awareness about the importance of gender equity and the rising number of women in medicine, women remain persistently underrepresented in pain medicine and anesthesiology. Pain medicine ranks among the bottom quartile of medical specialties in terms of female applicants, female trainees, and proportion of female practitioners. Female pain medicine physicians are also notably disadvantaged compared with their male colleagues in most objective metrics of gender equity, which include financial compensation, career advancement, public recognition, and leadership positions. Increased gender diversity among pain medicine physicians is vital to fostering excellence in pain research, education, and clinical care, as well as creating a high-quality work environment. Pain medicine stands at a crossroads as a specialty, and must examine reasons for its current gender gap and consider a call to action to address this important issue.