ChatGPT Season 5 of the series spans four decades, from the 1960s to the 2000s, following the professional and personal journey of Midge. In the early '60s, Midge faces professional challenges but lands a writing role on The Gordon Ford Show, where she navigates a competitive, male-dominated environment. The story reveals future events: Midge discovers Susie's mob connections, which inadvertently involve Joel in unlawful activities, leading to Susie's firing. As Midge's career skyrockets, Lenny Bruce, another character, battles with drug addiction. Midge's rise to fame as a comedy star is juxtaposed with her turbulent personal life, marked by several marriages, the loss of close ones, and tense relationships with her grown children, culminating in eventual reconciliations. Through these ups and downs, Midge maintains a close bond with Joel.