(December 29, 1914 - January 21, 1989) U.S.A.
Billy Tipton was actually born Dorothy Lucile Tipton in Oklahoma City. Her father was an aviator and car racer, while her mother was a housewife. Her parents divorced when she was only four years old, and Dorothy was sent to live with her aunt in Kansas City.
This move was vital in developing Dorothy's interesting future. Her aunt began to teach her piano and a love for music. In the 1920s, Kansas City had a big jazz scene, that by the age of 16, was already influencing Dorothy. She began attending jazz clubs, and knew playing piano and saxophone would be in her future.
At age eighteen, Dorothy Tipton decided to audition in several jazz clubs throughout the area. Unfortunately, the club owners all told her the same thing. She was a very talented artist, but they simply would not hire a female. It was at this point in 1933 that Dorothy, with the help of her cousins, became Billy Tipton. She took his father's nickname, Billy, and more actively worked to present as male.
Billy Tipton was careful to leave as little legal documents as possible. He finished highschool, but failed to request graduation documents, as though already planning to leave his female birth identity behind. Early in his career, even when most of his friends still knew that he was female bodied, he obtained legal documents listing him as male... again indicating that he planned to live his entire life as a man.
While, at first, he only fully presented as male while performing, by 1940, Tipton fully had transitioned to living full-time as a man. She taped her chest, cut her hair, and wore a suit to her next audition. As Billy Tipton, Dorothy Tipton not only received the job but quickly became a success.
In the early 1950s, Tipton started a seven-year relationship with Betty Cox, who later remembered him as "the most fantastic love of my life". Tipton hid his birth sex from Cox by explaining, in a story that he used for the rest of his life, that he had been in a serious car accident that resulted in damaged genitals and seriously broken ribs; in order to protect his chest from further injury, Tipton said, he had to bind it.
In order to keep playing jazz, without suffering from discrimination or judgment, Dorothy continued to live as a man for the rest of her life. After playing saxophone for several bands, she believed she had the talent to begin her own group. During the 1950s, Billy began the Billy Tipton Trio with childhood friend Lou Raines and musician Bill Pierson.
The Trio became a quartet with the addition of bass player Ron Kilde in 1954. In 1956, the group got a big break. A Tops Records agent heard the Trio in Santa Barbara and decided to sponsor their first album. Sweet Georgia Brown, was quickly followed by their second album Billy Tipton plays HiFi on the Piano.
Billy Tipton, center, with bandmates Ron Kilde, left, and Dick O'Neil, right, c. 1955. Photo c/o AP
In 1958, Billy Tipton and the band were offered a chance at national fame. The band was granted the position as house band in Reno, backing famous artists such as Liberace. Billy, against the desires of the other members, turned the job down to work at a booking agency and to play at night. It is believed Billy feared the fame would reveal her "cross-dressing, lesbian lifestyle."
She did not seek fame per se, but rather ran from it. Billy Tipton simply desired to be free from scrutiny and free to play jazz. Residing in Spokane Washington with her family for many years, Billy played only occasionally in local night clubs.
There is some debate whether the many romances in Billy's life began as a cover, or whether she was truly a lesbian. Billy was said to have had five "Mrs. Tiptons", women who though records have not been found, lived with Billy as man and wife. Even these woman, along with her three adopted sons remained unaware of Billy's identity as a woman.
Astounding as it may seem, Billy was able to keep her secret until his death. "She kept her breasts bound by elastic bandages, explaining that her ribs had been broken in a car accident and the bandages helped prevent pain. Sexually, he made love only in the dark, often half-clothed and was deft at the use of a prosthetic device."
In 1960, Tipton ended his relationship with Cox and settled in Spokane, Washington with nightclub dancer Kitty Kelly, known professionally as "The Irish Venus". The couple adopted three sons and participated in their local PTA and Boy Scouts; the relationship, however, was not happy. In the late 1970s, Tipton left Kelly, moved into a mobile home with his sons and lived, in poverty, until his death.
By the late 1970s, however, Tipton's worsening arthritis forced him to retire from music.
Tipton died in 1989 and was "outed" by the coroner. Soon after, people speculated as to why a "woman" would live fifty-six years as a man, not telling even his wife and kids! The notion that he was transgendered did not enter their thoughts. Tipton's son, William, learned that his father was a transgender man. While the family sought to keep Tiptons birth sex a secret by having Tipton cremated, they soon were approached by media organizations and they went public with the story.
All of Billy's wives stressed the fact that Billy was not fond of physical affection, and they simply accepted that as part of the relationship. After the discovery, friends and family members, though obviously shocked, only had kind words to say about Billy. One of the sons responded, that he will only think of his father "simply as Dad."
Newscoverage after his death in 1989
He was a She ...
Biography by Diane Wood Middlebrook
Suits Me: The Double Life of Billy Tipton
Source: http://www-music.duke.edu/jazz_archive/artists/tipton.billy/01/ - http://lgbt-history-archive.tumblr.com/ - et alii