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
. . .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.
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
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
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.
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.