I’ve recently become fascinated with people who lived their entire lives as another gender, and especially fascinated when women live as men to do jobs that they wouldn’t have been allowed to do otherwise.
My two favorite stories:
James Barry was born in 1789 and graduated from the University of Edinburgh. After graduation, he started work as a doctor in the British Army. He was placed as a Regimental Assistant, then a Hospital Assistant, then Assistant Staff Surgeon, serving in India and South Africa. He performed the first successful Caesarian section where both mother and child survived, and then became an Inspector General and the Principal Medical Officer. Along the way, he got in lots of fights, was arrested and deported from Saint Helena for “internal politics”, and was generally known for being feisty and opinionated. During the Crimean War, he actually got into an argument with Florence Nightengale. (!!!) He was insistent on good hygiene and treating the poor with dignity, and his only constant companions were his manservant John and his pet dogs.
When he died in 1865 of dysentery, the female chairwoman who examined his body discovered that he was actually a female, and told everyone at the funeral. James Barry was actually Margaret Ann Bulkley, and she took her uncle’s name when she registered for college so that she could become a doctor.
Billy/Dorothy “Tippy” Tipton was born in 1914, and was in school bands from the get go. He was an accomplished musician, and when he started leading bands in 1936 for radio stations, he was dressing as man on stage, but by the 40s, he was living as a man onstage and off. During this period, he was living with a woman named Non Earl Harrell who was believed to be his lover. They broke up in 1942. He then lived with a woman named Betty Cox, who said that she had a heterosexual relationship with Billy. How? Well, he taped up his chest and wore a cup every day, and told Betty (and subsequent women) that he was injured in a car accident that left his ribs and genitals permanently messed up. After Betty, he lived with a popular stripper named Kitty, and together they adopted several children. Billy was signed in the 50s and toured and released albums as The Billy Tipton Trio.
Kitty has said about Billy: “He gave up everything… There were certain rules and regulations in those days if you were going to be a musician.” Their children became rambunctious and Billy and Kitty separated over how to raise them, with Billy becoming the primary parent.
Late in life, Billy became a talent booker and would play standards as different characters like Liberace and Elvis. He then became a teacher to other musicians. He retired due to arthritis, and in his 70s, his health started to fail. He attributed it to emphysema, but he was wrong: it was a severe hemorrhaging peptic ulcer. As doctors tried to save Billy, his son William discovered that his father was, in fact, a woman. The doctors told the entire family. When he died, Kitty tried to have his body cremated so no one would find out, but one of the sons went public.
Please enjoy the Billy Tipton Trio with “Sweet Georgia Brown”.