BILLY TIPTON, American musician born (d. 1989); American jazz pianist and saxophonist Tipton was born in Oklahoma City, Oklahoma. She grew up in Kansas City, MO, where she was raised by an aunt after her parents’ divorce. After the divorce, she rarely saw her father, G.W. Tipton, a pilot who sometimes took her for airplane rides. As a high school student, Tipton became interested in music, especially jazz. She went by the nickname “Tippy.”

In 1933, Tipton began dressing like a man, which allowed her to blend with the other members of the jazz bands she played with in small Oklahoma bars.

As she began a more serious music career, she decided to adopt a male persona, calling herself by her father’s nickname, Billy, and presenting herself consistently as male. She had a face which could easily pass as male, so she could bind her breasts and pad her pants to create a believable illusion of masculinity. The change to life as a man made it possible for Tipton to continue a career in jazz, where opportunities for women were more limited. At first, she was male only in her public persona, but by 1940 she was presenting herself as male both publicly and privately.

Tipton gradually gained success and recognition as a musician. In 1936, he was the leader of a band playing on KFXR. In 1938, he joined Louvenie’s Western Swingbillies, a band which played on KTOK and at Brown’s Tavern. In 1940 Tipton was touring the Midwest playing at dances with Scott Cameron’s band. In 1941 he began two and a half years playing at Joplin, MO’s Cotton Club with George Mayer’s band, then toured for a time with Ross Carlyle, then played for two years in Texas.

Early in her career, Tipton cross-dressed only professionally, and still lived in her private life as a woman. She spent those early years living with a woman named Non Earl Harrell, in a relationship which other musicians recognized as lesbian. The relationship ended in 1942.

Tipton’s next relationship, with a singer named 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 which included sex. He kept the secret of his biological sex by telling Betty that he had been in a serious car accident which required him to bind his chest to protect broken ribs, and which had badly damaged his genitals. This is the story he would also tell subsequent women with whom he was involved. Betty was not faithful to Tipton, but was fond of him nonetheless, and remembered him as “the most fantastic love of my 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 was biologically female, since he dressed in private, had sex only in the dark, and preferred to touch, not to be touched.

Two of Tipton’s female cousins were the only persons privy to both sides of his life, and Tipton kept in contact with them for years. In 1960, he ended a relationship with a prostitute to be married to nightclub dancer and stripper Kitty Kelly (later Oakes), who was known professionally as “The Irish Venus”. Tipton was never legally married, but several women had drivers’ licenses identifying them as Mrs. Tipton. 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. Although Kitty denied having any knowledge that she was married to a transman, John and Scott did not believe her. William described Tipton as a good father who loved to go on Scout camping trips.

Their adopted sons became difficult to manage during their adolescence. Because of the couple’s ongoing arguments over how they should raise the boys, Tipton left Kitty, moved into a mobile home with their sons, and resumed his old relationship with Maryann. He remained there until his death a year later.