Brought to you by Pistol Pete Billy Lee Tipton (born as Dorothy Lucille Tipton; December 29, 1914 – January 21, 1989) was an American jazz musician and bandleader who lived as a man for nearly 50 years. Tipton found modest success as a professional musician, but until his dying moments, the fact that Tipton had been born biologically female was known only to a few people.
Dorothy Tipton was born in Oklahoma City. As a high school student, she went by the nickname "Tippy" and became interested in music, especially jazz. She studied piano and saxophone, but her school had a policy forbidding girls to play in the school band.
In 1933, Tipton began dressing as a man, which allowed Tipton to blend with the other members of the jazz bands with whom Tipton played in small Oklahoma bars. As Tipton began a more serious music career, Tipton adopted her father's nickname, Billy, and more actively concealed her female body by breast-binding and packing. At first, Tipton only presented as male in performance, but by 1940 Tipton was living as a man in her private life as well.
During a performance on tour at King's Supper Club in Santa Barbara, California, a talent scout from Tops Records heard them play and got them a contract. The Billy Tipton Trio recorded two albums of jazz standards for Tops.
After the albums' success, the Billy Tipton Trio was offered a position as house band at the Holiday Hotel in Reno, Nevada, and Tops Records invited the trio to record four more albums. Tipton declined both offers, choosing instead to move to Spokane, Washington, where he worked as a talent broker and the trio was the house band at Allen's Tin Pan Alley, performing weekly.
As noted, early in his career, Tipton cross-dressed only professionally, continuing to present as a woman otherwise. He spent those early years living with a woman named Non Earl Harrell, in a relationship which other musicians thought of as lesbian. The relationship ended in 1942. His next relationship, with a singer known only as "June", lasted for several years.
For seven years, Tipton lived with Betty Cox, who was 19 years old when they became involved. According to Betty, they had a heterosexual relationship. Betty remembered him as "the most fantastic love of my life." Tipton kept the secret of his extrinsic sexual characteristics from Betty by inventing a story that he had been in a serious car accident which had badly damaged his genitals and broken some ribs, and that to protect the damaged chest he had to bind it. From then on, this was what he would tell the women in his life.
After Betty ended their relationship, he quickly became involved with Maryann Catanach, a prostitute. According to Maryann, theirs was a normal sexual relationship, and she did not know that Tipton had female genitals, since he dressed in private, had sex only in the dark, and preferred to touch, not to be touched.
In 1960, he ended this relationship to settle down with nightclub dancer and stripper Kitty Kelly, who was known professionally as "The Irish Venus." Kitty said that they never had sex but had an otherwise normal life. They were involved with their local PTA and with the Boy Scouts. They adopted three sons, John, Scott, and William. After Tipton's death, Kitty gave several interviews about him and their relationship. In early interviews, she said, “He gave up everything... There were certain rules and regulations in those days if you were going to be a musician,” in reference to breaking into the 1920-30's music industry as a woman, and, “No one knew. It was the best-guarded secret since Houdini.” But in later interviews she denied having known that Tipton was a trans man, a denial that sons John and Scott did not believe. William described Tipton as a good father who loved to go on Scout camping trips.
In 1989, at the age of 74, he had symptoms he attributed to emphysema and refused to call a doctor. In actuality he was suffering from a hemorrhaging peptic ulcer, which, untreated, was fatal. It was while paramedics were trying to save Tipton's life, with son William looking on, that William learned that his father was biologically female. Tipton was pronounced dead at Valley General Hospital. The coroner shared the revelation with the rest of the family. In an attempt to keep Billy's secret, Kitty arranged for his body to be cremated. But one of his sons went public with the story.
Two wills were left by Tipton; one handwritten and not notarized which left everything to William Jr. and the second, notarized, leaving everything to Jon Clark. A court upheld the first will, and William inherited almost everything, with John and Scott receiving a dollar each.
Source: Wikipedia
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