Gender Bender

Diane Wood Middlebrook’s “Suits Me: The Double Life of Billy Tipton” is alternately a fascinating and somewhat frustrating telling of the curious and complex life of the jazz musician who was born in 1914 as a woman but lived as a man from age 19 until her death in 1989. The author of “Anne Sexton: A Biography,” in which she famously (and with much controversy) included transcripts of tape-recorded sessions between the poet and her psychiatrist, Middlebrook faces an inverse challenge here: How to capture a life in which there is an almost complete absence of intimate written (or recorded) source material of any kind.

In addition, Tipton was an illusionist of a high and mysterious magnitude. She lived in a time and in places, the mid-century Midwest and Northwest, where privacy was still respected. A combination of chance and the force of her personality allowed her, remarkably, to conduct five relationships with women who claimed they never guessed her true (that is, biologically true) identity. All this contributes to Tipton’s fundamental elusiveness. A further challenge to Middlebrook is the fact that Tipton happened to come along--as a subject--at a moment when, as she writes, “gender had come into its own as a theme in art and politics. The very term ‘gender’ was now a marker on the grave of venerable assumptions about the importance of sex difference.” After her death, Tipton became, and Middlebrook to a degree sees her as, “a poster boy for raising consciousness about the confusions of sex (biological) and gender (culturally meaningful physical and social attributes).”

These ideas are well worth exploring. Yet the problem is that the combination of Tipton’s silence and her arrogation by the poster makers and polemicists puts especially sharp thorns in the path of the biographer. Middlebrook often seems confounded by the central enigma of her subject--as indeed who wouldn’t be?--yet rather than acknowledge Tipton’s inscrutability, she tries out a range of theories, many of them constricting. Imagine how extraordinary it would be, just once, to meet a biographer who allowed that the answers were beyond her or his reach, who said, in effect, “I have a singular and original story to tell, but I must warn you, I will not, ultimately, be able to tell you what it means.” Such an approach might, in Tipton’s case, have led to a deeper and far more poignant recognition of the brave things she was able to achieve (along with those she was prevented from accomplishing), and it might have directed a surprising light into some of the more hidden corners of the human psyche and heart. Instead, too often a tone of prurient and reductive detective work prevails.

With regard to facts, figures and chasing down and interviewing sources, Middlebrook’s sleuthing is energetic and informative. Born in Oklahoma City as Dorothy Lucille to George William and Reggie Tipton, a “good-looking, fun-loving, hot-tempered, sexy, ambitious” couple, Tipton learned to play the piano from her mother (specifically ragtime, cakewalk and the blues) and acquired a sense of daring, it appears, from her father, who was a mechanic, a race car driver and a pilot.

In 1927, however, when Tipton was just entering her teens, the fun fizzled. Her parents separated and in 1929 shipped her and her younger brother to an aunt in Kansas City, Mo., marking the children with a powerful sense of abandonment. In Kansas City, Tipton’s education was advanced, both in terms of worldliness (her Aunt Bess had money and was moderately adventuresome) and music: She received professional instruction and was introduced to the city’s thriving jazz scene. Three years later, defying her aunt’s plans for her career (she was to be a classical musician), Tipton returned to live with her mother and soon undertook what Middlebrook describes as “one of the twentieth century’s most sustained acts of female defiance”: She bound her chest in a worn-out sheet, put on men’s clothes and went to work as a professional male musician. (Her first job was not as a pianist but as a sax player.)

Why? Middlebrook suggests a number of factors. First, there were the economics: At the height of the Depression, jobs for musicians were scarce. Then, there was the gender quota: Jobs for female musicians were scarcer still. (They were not, however, totally unavailable. At the time, nearby Kansas City was a base for several black female pianists, and in the early 1940s, it was home to an all-girl band, though Roberta Ellis, the band’s drummer, maintained in later years that “if I had been able to get into a male band, with musical expertise all around me, I probably would have become a better musician.”) Middlebrook argues that, in addition, Tipton had a sense of “entitlement bestowed by talent and by the affluence of her early life”--nothing, it seemed, was going to keep her from performing professionally. Finally, she was able, through the style of heterosexual masculinity she developed--”the persona of an upbeat, sharp-dressing, warmhearted, good-humored big brother”--to address emotional problems left over from the breakup of her family: She became a protector of her mother and other frail women, “the kind of man who solved the problems created for her mother’s kind of woman by her father’s kind of man.” Deprived of her parents at a key point in her adolescence, Dorothy--now Billy--turned herself into an amalgam of both of them, or of their imagoes at least.

Although Tipton first cross-dressed in the early 1930s, it wasn’t until 1940 that she assumed a masculine identity in all contexts and relationships. By living as a man, Tipton gave up all ties to her father, who disowned her, and to her brother, with whom she never reconciled. She adopted elaborate habits and behaviors that allowed her to achieve professional success playing in other people’s, and eventually heading her own, swing and jazz bands, trios and quartets, although the demands of sustaining these behaviors may ultimately have caused her to retreat from fame. These same behaviors allowed Tipton to conduct virtual marriages with five women, unions that were so convincing that one of Tipton’s “wives,” Betty Cox, with whom Tipton was intimate sexually, said, “I cannot in my wildest dreams accept the fact that I finally know to be true.” With another, Kitty Flaherty, Tipton was said (by Flaherty herself) to have had no sexual relationship, though they did adopt and raise three children together and live as husband and wife for many years.

Whether these women spoke truthfully to Middlebrook remains unclear (if one is concerned about being labeled homosexual, one might prefer to be seen as sexually naive or abstemious) and in the end is possibly irrelevant. Indeed, one of Middlebrook’s more disappointing choices in this biography is the way she succumbs to the dubious idea, which is exceedingly prevalent in our culture at the moment, that once the bedroom door has been thrust open, a human being’s inner life is thought to be explained or understood. This is not to say we don’t read with interest the first (though not the second or third) time that Middlebrook presents her discoveries: Tipton was never seen completely undressed; she continued to bind her chest all her life, claiming an old injury to her ribs; she wore a prosthesis-filled jockstrap under her underwear; she was said to peel off condoms after sex. But this National Enquirer-like expose reveals far less about Tipton’s essence, her soul, than Cox’s retrospective remark that “I wish I could shout to the world how great Billy was as a person, friend, confidant, and a love.”

Middlebrook subsumes these magnificent mysteries of the human heart and psyche to what feels, at moments, like an all-too-predictable impulse to see Tipton’s life as having strong pathological dimensions. She stresses the danger of exposure that Tipton lived with but gives no example (other than some mild occasional heckling from people in the audience and a handful of nonthreatening collegial remarks) of her ever being confronted in a menacing way. She asserts that by hooking up with innocent Cox, Tipton displayed a shrewdness that “diminish[ed] [her] moral stature”--but one has to wonder how morality enters into this discussion, especially in view of Cox’s apparently genuine affectionate description of her life with Tipton. And while Middlebrook seems to admire the completeness of the illusion Tipton wrought, by defining her as “an artist, improvising with attitude, voice, and gesture” and insisting that “she was the actor, he was the role,” she flattens out Tipton’s unique humanness. She also diminishes the art Tipton did produce. Somewhat lost in Middlebrook’s narrative are testimonials like this one from saxophonist Lew Raines: “Billy’s love for music, Billy’s feeling toward those who made music with him, was overwhelming. . . . There was only the pure and total satisfaction of sitting at a keyboard and having people listen, join in, participate--that was satisfying beyond description.”

As a man, certainly, Tipton was a hybrid. Like a mirror image of female impersonators who exaggerate the women they depict, Tipton shaved, smoked a cigar and a pipe, told lewd and gay jokes and replaced his fourth wife (because she crocheted too much!) with a gorgeous ex-stripper. Yet he was also a loving caretaker of dogs, young men, vulnerable women and children. Tipton the male bandleader ultimately came up short: Middlebrook reasons that he avoided conflict that might lead to grudges, fights and exposure of his true identity--as well as exposure of another kind, to a wider audience. Tipton the father seemed to have a related problem: In Flaherty’s estimation, he refused to punish or discipline his sons or to hold out clear expectations for their maturity and accomplishments. He was not firm enough; he let them grow up wild and unguided.

Middlebrook leaves us with many disconnected but intriguing Billy Tiptons. Two in particular stand out. The first is a palpably sad Tipton, a human being who was cut off from like-minded and like-spirited people; who experienced a conditional intimacy with human beings; who because of her fabricated identity came up against possibly artificial limitations to her career; who could not comfortably seek medical attention as she aged; and who, though she built a close relationship with only one son, William, left him feeling painfully deceived by the post-mortem disclosure of her sex. For this Tipton one feels regret. What an extraordinary gesture of trust and daring it would have been if Tipton had been able to reveal herself to William and had shown him, as Middlebrook has effectively shown us, how alternate or imagined lives are possible and within reach of certain women and men.

The other Tipton was the human being who loved deeply, who was profoundly committed to her music, who gave of herself, who delighted and entertained people, and who felt so unconstrained that she believed she could make herself up to a most unusual degree. To one of two cousins who knew Tipton’s identity and with whom she remained in contact, she said near the end of her life, “Some people might think I’m a freak or a hermaphrodite. I’m not. I’m a normal human being. This has been my choice.”

Billy Tipton’s choice speaks out over her biographer’s attempts to categorize her or pin her down. As jazz historian Jim Merod remarks in a most percipient and sympathetic evaluation Middlebrook quotes, “Playing music of this kind at a superior level offers a sublime self-overcoming. Billy’s act looks Whitmanic--he affirms a vivid life of self-invention against implacable odds.”