3. Ernest Hemingway's Son-Turned-Daughter: Gregory/Gloria

Gregory had a mostly estranged relationship with his father, who blamed him for his mother Pauline’s death, supposedly caused by shock at Gregory’s arrest in 1951, when he was caught entering a women’s restroom in a theatre.

Gregory was, according to The Telegraph, a college dropout who “was discharged from the U.S. Army, drank heavily and could not hold down a job.” He fathered eight children during his first four marriages while simultaneously struggling with his sexual identity. His daughter, Lorian, wrote in her memoir Walk on Water: “I never had a clue until my mother told me that he sometimes wore her girdle and painted his nails a bright, clean red. ... I've seen pictures. He looks like Ethel Merman."

Gregory’s cross-dressing eventually led to a sex-change operation in 1995, after which he went by the name Gloria. Gloria spent her last five days alive in a woman’s prison after being arrested on Key Biscayne for indecent exposure, walking around without any clothes on, though holding a dress and high heels. She died in prison of hypertension and cardiovascular disease.