Billy Tipton


By Sally Lehrman

Biographer Diane Middlebrook found herself face to face with questions about sex identity when she began researching the life of jazz musician Billy Tipton for her coming book. Tipton, a saxophone and piano player who led popular dance bands in the 1940s and early ’50s, made his career traveling through small towns on the Southwest and Northwest jazz circuits. He lived a glamorous and exuberant life, made lots of friends and married several times.

Billy TiptonBilly Tipton

Tipton eventually settled down in Spokane, Washington, married a former stripper named Kitty and adopted three sons. But jazz fever died out as Tipton grew older, and he spent his last years alone in a trailer park with little money. In 1989, at age 74, what Tipton thought was emphysema turned out to be a hemorrhaging ulcer. His youngest son called an ambulance and watched as the paramedics who tried to resuscitate his father uncovered a startling truth: The dying man had the body of a woman.

As Middlebrook, a Stanford professor of English, began talking with Billy’s wives, children, cousins and colleagues, she asked about sex identity. She asked about sex. She asked about the way Billy dressed, the way he talked, the way he presented himself while making love. Middlebrook struggled to find the words to describe him. Born as Dorothy, Billy had fooled men and women alike for 50 years. The first time the young woman passed as a man it was a joke ­ and a concession to the economic pressures of the Depression

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