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Right Answers Mostly

Katharine Hepburn: Hollywood’s Rebellion in Trousers

December 8, 2025·1h 2m

In this week’s episode, we dive into the life of Hollywood’s original “I’ll do it my way” girl: Katharine Hepburn. From growing up in a fiercely progressive household (her mom was literally fighting for birth control while her dad was lecturing on public health) to reinventing herself as the pants wearing, ice-bath-taking, golf obsessed wellness influencer of 1930, Hepburn was never going to fit the studio mold. We unpack her rise from east coast tomboy to four time Oscar winner, the rumors, the reinventions, the romances (real and speculated), and the unapologetic independence that made her a legend. It’s a story of privilege, pressure, feminism before we called it that, and the price of living life on your own terms in old Hollywood. History is just gossip, and this is Hepburn like you’ve never heard her.