Katharine Hepburn played cross-dressed and drag characters long before they became popular. She starred in the 1935 romantic comedy Sylvia Scarlett, in which she was seen as a young woman who pretends to be a boy named Sylvester as part of a con with Cary Grant.
Unfortunately, the film was a significant disappointment and did not enhance her career.
The book Moxie: The Daring Women of Classic Hollywood by Ira M. Resnick and Raissa Bretaña includes chapters dedicated to the legendary, including screen sirens Hepburn, Marlene Dietrich, Bette Davis, and Lauren Bacall. Despite the film’s box office crash, it got the mill churning about its star’s sexual orientation. The film ignored the traditional femininity standards to which the heroines were expected to adhere.
It also included a scandalous kiss between Hepburn and her female costar, Dennie Moore. Hepburn — who passed away in 2003 — called the film ‘a real disaster,’ according to the book. “This subversive gender-bending fueled rumors about Hepburn’s sexuality — which became a topic of debate after she divorced her husband [Ludlow Ogden Smith] in 1934 and began living with a female companion,” the book mentioned.
It claimed that the actress had an ‘aversion’ to celebrity culture and did not intend to propel the illusion of movie stardom. Therefore, she never dressed glamorously, signed autographs, or gave interviews. The book also mentions a transcript from her 1934 interview with Motion Picture Magazine in which she said, “I’m not living my life for Hollywood or publicity, and I never will. Why should I have to change my personality?”
Hepburn was famously in a long-term relationship with her nine-time costar, Spencer Tracy, until his death. However, Hollywood lures claim that their courtship was actually a platonic one meant to camouflage both the star’s sexual orientations. Despite Hepburn’s personal struggles, she managed to create a legacy with her “tireless dedication to her career,” says the book.