Rank the complex women who shaped the world of Sterling Cooper and beyond in this definitive character ranking. From powerhouse figures like Joan Holloway and Peggy Olson who redefined workplace dynamics, to the enigmatic Betty Draper and the tragic Anna Draper, each woman brought unique depth to the series. The list includes Don's various romantic entanglements like Midge and Sylvia, Pete's complicated relationships including his wife Trudy and neighbor Brenda, plus essential supporting characters like Dawn and Jane. Whether they were secretaries, wives, mistresses, or independent spirits like Stephanie Horton, these women navigated the challenging landscape of 1960s America with varying degrees of agency, ambition, and resilience. Who truly deserves top-tier status in this unforgettable ensemble?