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Billy was born as Dorothy Lucille Tipton in Oklahoma City, Oklahoma, USA. In 1933 he took a role of a male musician and finally got into a band in Kansas City, Missouri.
During the Great Depression and World War II, he played with bands of Jack Teagarden and Ross Carlyle , among others. In 1954 he formed the Billy Tipton Trio with drummer Dick O'Neal and bass player Ron Kilde and played with them for more than ten years. After his career he settled down as an entertainment agent in Spokane, Washington.
Tipton was married four times, first time in 1960 to a nightclub dancer Kitty Oakes. He told each of his wives that he had been in a grave car accident that had left him with unhealed ribs, genital disfigurement and sterility. He also adopted three boys and became a scoutmaster. His parents and one cousin apparently knew the truth.
In 1989 he suffered from hemorrhaging ulcers and refused to call a doctor. After his death in January 1989, the coroner told his family the truth. None of his adopted sons, ex-wives, associates or band members have admitted to previously knowing the gender assigned to him at birth.