Musician and bandleader Billy Tipton was born in Oklahoma City on December 29, 1914. Tipton led one of the more unusual lives of any of the people we have featured in this column. Assigned female gender at birth, Tipton began to identify as male around 1933 and by 1940 was living life as a male in both his musical and personal life.

Tipton was born Dorothy Lucille Tipton to parents who divorced when she was four. Dorothy was sent to live with an aunt in Kansas City and had developed an interest in music, and specifically jazz, by high school. She learned to play piano and saxophone but was refused membership in the school band because it was for boys only. Shortly after finishing high school and returning to Oklahoma, Tipton was playing and touring with the Banner Playboys, a western swing band popular in the southwestern United States.
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As to the decision to live full time as a male Historylink.org reports that “…one biographer, Sally Lehrman, hypothesized was that the act was likely ‘a concession to the economic pressures of the Great Depression and the reality that women jazz musicians didn’t get jobs.’ Diane Wood Middlebrook, another writer who wrote of Tipton’s double life, added that ‘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.’”

In 1949 Tipton was playing piano in George Meyer’s band that performed regularly at the Boulevard Club in Coeur d’Alene, Idaho sharing the bill with groups like the Ink Spots and Billy Eckstein’s orchestra. By 1951 Tipton had a solo piano gig at the Elk’s Club in Longview, Washington before forming his own trio. In 1956 the trio was signed to a recording contract with Tops Records and made two albums with the label. Both were released in 1957. Following the success of the two records, Tipton and his trio were offered gigs at the Holiday Hotel in Reno, Nevada and as the opening act for Liberace. Tipton declined both offers and moved to Spokane, Washington where his trio had a weekly gig.

By the late 1970s Tipton retired from performing due to worsening arthritis and concentrated more on work as a talent broker. By 1989 Tipton’s health was declining rapidly and he refused to see a doctor, assuming he was experiencing symptoms of emphysema due to a lifetime as a heavy smoker. In fact, he was suffering from a hemorrhaging peptic ulcer which eventually killed him. While paramedics worked on him it was discovered that Tipton was physically female, a development which "came as a shock to nearly everyone, including the women who had considered themselves his wives, as well as his sons and the musicians who had traveled with him. “

Following Billy Tipton’s death there was a good deal written and said about him in the popular media and his life has inspired numerous plays, musical compositions and documentaries, as well as the name of the Seattle-based musical group The Tipton Sax Quartet.

Here is a link to a cut from the Billy Tipton Trio from one of their mid-1950s recordings:

"SWEET GEORGIA BROWN"