Suits Me: The Double Life of Billy Tipton


Suits Me is the biography of a jazz musician named Billy Tipton, who grew up as Dorothy Tipton in Oklahoma City and Kansas City but lived as a man from the time she was nineteen until she died at age seventy-four. Billy Tipton's death in Spokane Washington, made news all over the world, not because he was celebrated as a musician but because of the scale of his deception -- he had been "married" to five women and had reared several adopted children -- and the scarcity of ready explanations endowed the skimpy ...

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Suits Me is the biography of a jazz musician named Billy Tipton, who grew up as Dorothy Tipton in Oklahoma City and Kansas City but lived as a man from the time she was nineteen until she died at age seventy-four. Billy Tipton's death in Spokane Washington, made news all over the world, not because he was celebrated as a musician but because of the scale of his deception -- he had been "married" to five women and had reared several adopted children -- and the scarcity of ready explanations endowed the skimpy available facts with the aura of myth.

Locked away in Billy's office closet lay the record of a lifetime's achievements: clippings and photographs documenting the transformation of Billy from she to he, and a legacy of annotated comic routines, musical arrangements, and program notes that tell an extraordinary story. These reveal how, night after night, Billy scattered clues and riddles about the drag she wore, including risque gags about homosexuality and jokes that called attention to the disguise. These convey the pride of an artist in his success in achieving a lifetime of deception -- and they wree so bold that they helped conceal Billy's secrets.

Suits Me tells the life story of this brilliant deceiver with brio and pathos. To live at once in two skins, one of each sex, is not an everyday experience, yet we can hear Billy's loves and ambitions through the voices of those who knew him -- his "wives," his family, his musical colleagues, and those who encountered him on the road as he traveled with the Billy Tipton Trio from town to town, bandstand to bandstand, gig to gig, during the jazz decades.

A masterpiece of skillful detection and perceptive storytelling, Suits Me not only casts a warm eye over the spectrum of the sexes but chronicles tanktown show business over a period of fifty years. Illustrated by Billy Tipton's photographs, this book also reveals, in words, music, history, and psychology, any number of secrets, plumbing mysteries about the American family that few of us have dared to face.

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Editorial Reviews

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The Barnes & Noble Review
Diane Wood Middlebrook, a poet who also writes the occasional biography, had just seen the publication of her biography of Anne Sexton when she was approached by a woman named Kitty Tipton Oakes at a speaking engagement. Oakes was looking for a writer to put together a book about her late husband, Billy Tipton, mainly so that there'd be source material on paper if a movie based on Tipton's life story were ever made. This was fortuitous for Middlebrook, not only because she has written more than just a biography of a complex person, but because she has written a wonderful love letter to a century through the life of Billy Tipton.

Who was Tipton? At face value, Tipton was someone who biologically was a woman, but lived all but 18 of his 70-something years as a man. Middlebrook delves deep into the life surrounding the ultimate self-made man and, in the process, has sketched a century of Americana within the canvas of this fascinating life. Billy's life was less fascinating for what the gender-bending Billy did than for the century Billy inhabited and the forces around him that he was working against.

Middlebrook begins her unraveling before Billy was born, essentially at the birth of Oklahoma as a state in the late 1800s, in order to re-create the world that Billy entered in the early teens of the century as Dorothy Tipton. Dorothy's parents' relationship was complicated, and after their son, Bill, was born, divorce and custody battles reared their ugly heads. Dorothy and her little brother were often raised by their father's sisters, who provided a rich world for the two toexplore.Meanwhile Dorothy was learning music as she grew to adulthood, and this in Kansas City, which was then exploding with ragtime and jazz. By the time Dorothy was 18, she wore male drag, and was fairly quickly disowned by her father. Interestingly, to avoid confusion of names, biographer Middlebrook chooses to call Dorothy's father G. W. but he was known as Billie to almost anyone who knew him. Thus, when Dorothy began to play professional gigs, her persona took the name of both her then-distant father and her brother.

Billy Tipton came into being in the last years of the Jazz Age. Through the Depression and World War II, he got work in clubs, hobnobbing with the royalty of that style of music, as well as living an itinerant but rewarding life as a pianist and saxophonist for various bands. From this point on, the male persona of Billy was formed, and soon there would be no turning back. Through wives and the adoption of children, Billy became known as a man. As time went on, the subterfuge to keep his secret from most around him became a greater and greater burden.

A minor complaint I have with this biography is that Middlebrook doesn't quite seek to understand the inner workings of Billy Tipton. I always felt as if the biographer remained on the outside looking in, that the gender-defying friendships Billy had with women outside his marriages were considered a bit as oddities rather than perhaps a fully integrated world. This aside, however, Middlebrook's strength in this story is to capture, almost as if on film, the early century of this country, with Billy Tipton as something of an icon of the way times changed. Billy Tipton left no memoir, no notes about his reasons for leaving Dorothy behind and acquiring Billy. One assumes that part of the original masquerade was to keep working with jazz bands as "one of the guys," but of course, as Billy takes this persona beyond his days as a musician, it takes on a much deeper meaning than any mask or cover could. Billy Tipton was, in the end, a man, defying outward biology and instead responding to his own inward nature.

Middlebrook has written a rousing story of the 20th century as well as of the life of Billy Tipton. Suits Me: The Double Life of Billy Tipton is a bit misnamed, since it implies a bit of a ruse on Billy's part. I'd prefer to believe that Billy Tipton led a life that was true to himself. I highly recommend Suits Me, as a chronicle of Billy Tipton's, and the century's, life.

Douglas Clegg is the author of numerous horror and suspense novels including Dark of the Eye and The Children's Hour. His most recent short story, "O, Rare and Most Exquisite," can be found in the anthology The Year's Best Fantasy and Horror: Volume 10.

Catharine R. Stimpson
Suits Me: The Double Life of Billy Tipton is a fascinating exploration of the transvestite's powers and our contradictory submission and resistance to them. -- Women's Review of Books
Entertainment Weekly

. . .Middlebrook explores both gender and sex, as well as a range of related mysteries, in Suits Me. . . .a well-researched and exquisitely poised book. . . . .[Middlebrook] makes Tipton a person.

Maryanne Vollers

Billy Tipton was a hell of a ladies' man, for a lady. She was also a gifted musician, a loyal friend, an indulgent father of adopted boys and -- according to many women who lived with her at different times during the 50 years of her deception -- a satisfying lover. Few of her paramours, not to mention colleagues, had an inkling of her true gender. But that's the main question posed in Diane Wood Middlebrook's biography of the cross-dressing jazzman: What was Billy Tipton's true gender?

She was born Dorothy Lucille Tipton in Oklahoma City in 1914. Her mother, Reggie, gave her piano lessons and dressed her in ruffles. Her inventor-father, G.W. Tipton, was a daredevil pilot who took her up in airplanes. When, at 19, Dorothy began to live as a man, she took her father's nickname, Billy. By then, her parents were divorced and her father had faded from her life. But Billy Tipton, the self-made man, kept up a clandestine relationship with his/her mother and other relatives throughout his life.

What did Billy Tipton want? She wanted to make a living as a jazz musician during a time when women in the business were treated as freaks and novelty acts. She loved women, and wanted to live with them. So she cut her wavy blond hair, bound her breasts and wore a codpiece under full-cut suits. At first she was accepted among show people as a cross-dresser. But after she left Oklahoma for the life of a road musician, Tipton assumed a male identity. Tipton was intensely private, always locking the bathroom door, never turning on the lights in bed or letting her lovers touch her. She wore bindings, she said, because of an unhealed rib fracture. She was a small but lively character who told dirty jokes and played big brother to young musicians. This might not have worked in a more sophisticated place or time, but in the Dust Bowl of the '30s and '40s, and later the second-tier club circuit in the Pacific Northwest, Tipton passed with flying colors.

Tipton's cover was blown only after her death from bleeding ulcers in 1989. She hadn't seen a doctor in more than 50 years, but her autopsy showed that her body was that of a normal 74-year-old woman. Her fifth and last wife, Kitty Tipton Oakes, with whom she lived for 18 years, claims she was taken by surprise, as were their three adopted sons. Oakes approached Middlebrook, a poet and biographer, at a reading in Spokane and asked her to research Tipton's past, and perhaps to find an explanation for a lifetime of lies.

At first Middlebrook, whose last book was a biography of poet Anne Sexton, seems flummoxed by the lurid aspects of Billy Tipton's story. She tries to compensate for the lack of solid information about her early years by posing breathless questions ("Wild Billy Tipton! Why on earth did she do it?") or with sociological musings ("Possibly Billy was able to undertake this masculine role-playing with such self-confidence because she had entrusted the hidden female identity to her mother's keeping"). But as Middlebrook gains more authority with her subject matter, the book swings into life. Eventually we come to see Billy Tipton as a full human being, heroic and flawed, funny and tragic, motivated by love as well as fear.

Amazingly, even the "straight" women whom Tipton deceived didn't hold it against her. Betty Cox, who lived as Tipton's wife from 1946 through 1953, only learned Tipton's true identity after her death. She was "disturbed" to realize she had been sleeping with a woman, but still declared Billy "the most fantastic love of my life!" Billy Tipton the male jazz musician was generous to a fault. He would shower his wives with gifts, buy meals for his sidemen and later, when he went into the booking business, waive his fees if the bands needed money. The only thing he wouldn't share was his secret self. He died divorced and broke in a trailer outside Spokane. Under different circumstances, Tipton might have become a star. But in the end he chose privacy over money and fame.

Was Tipton a man trapped in a woman's body, an ambitious lesbian with a taste for straight women or a consummate actor playing the role of a lifetime? Middlebrook concludes that she was perhaps a blend of all that and more. Tipton left no diaries and no explanations -- just a stack of old 78s and trail of people who loved her for what she was: a good person and a gentle soul. -- Salon

Diane Middlebrook is now writing the life of Billy Tipton...It should be the paradimatic biography of our time.
Library Journal - Johnson
Middlebrook (Anne Sexton: A Biography, Houghton, 1991) will fascinate another large audience with her exhaustive account of the life of jazz musician Billy Tipton. Born Dorothy Tipton in Oklahoma in 1914, and reborn as Billy Tipton in 1933, Billy passed as a man until death at age 74.

Suits Me uses family interviews, anecdotes from musicians, jazz fans, lovers ("wives"), and friends to tell the story of a brilliant deception. The sensitive storytelling reveals thought-provoking perspectives about gender and the traditional American family, while capturing the social history of traveling jazz bands for 40 years. The family photographs and letters are particularly noteworthy in the exploration of Billy's life between the sexes, and there are extensive, enlightening notes and a bibliography. Highly recommended for academic and public libraries and/or libraries with women's studies or gay/lesbian/bisexual collections.

Robert Plunket
When jazz musician Billy Tipton died in 1989 at the age of 74, he was found out to be a woman. This came as quite a surprise to his five ex-wives and three adopted sons...

Diane Wood Middlebrook, an accomplished biographer and poet, does an excellent job of illuminating a life of deception and concealment by a person who turns out to have been admirable - talented, hardworking, funny, loving.
the Advocate

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Product Details

  • ISBN-13: 9780736648509
  • Publisher: Books on Tape, Inc.
  • Publication date: 1/1/2000
  • Format: Cassette
  • Edition description: Unabridged

Meet the Author

Dianne Wood Middlebrook is the author of several volumes of poetry and critism as well as the prizewinning bestseller Anne Sexton: A biography. The recipient of many fellowships and awards, she is a professor of English at Stanford University, where she has also served as the director of the center for research on women. She currently lives in San Francisco.

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Table of Contents

List of Illustrations x
Billy Tipton's Family Tree xii
Preface xiii
Author's Note xix
PART I Beginnings: 1889-1932
1. Born Naked (21 January 1989) 3
2. But Who Was She? (1889-1928) 12
3. Kansas City (1929-1932) 31
PART II From Dorothy to Billy: 1933-1940
4. The "In" Sex (1933-1934) 49
5. Graduation (1934-1935) 62
6. The Playboy (1935-1938) 77
7. Reggie's Daughter (1937-1940) 94
PART III The Impersonator: 1940-1948
8. Self-Made Man (1940-1943) 109
9. Swinging (1943-1946) 126
10. The Son-in-Law (1946-1949) 141
PART IV Rising: 1949-1958
11. Mobility (1949-1953) 159
12. Making It (1954-1958) 182
PART VSettling: 1958-1989
13. Man's World (1958-1961) 209
14. Family Man (1962-1979) 229
15. Out and Down (1980-1986) 256
16. The End (1986-1989) 270
Notes 285
References 311
Index 317
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