We’re kicking off Giving Tuesday early this year! Your donation today will be matched up to $10K, doubling your impact! If you donate $50 today, the Reader will receive $100.

The Reader is now a community-funded nonprofit newsroom. Can we count on your support to help keep us publishing?

One of the many pleasures of Madonna’s erotically charged video for “Justify My Love” was attempting to figure out who in the video was what, biologically speaking. The video itself provided some helpful clues: if I remember correctly, most of the women (besides Madonna) were sporting mustaches. But for a moment at least the video held out the possibility not only of misidentification but of misdirected desire. Putatively normal heterosexuals might find themselves lusting after a person of the wrong sex–a possibility that undoubtedly underlay much of the public anxiety the video provoked. And of course though the performers’ sexes were not immediately obvious, they all oozed sexuality of some sort. In fact Madonna has become the veritable queen of sexual ambiguity–wearing artfully adapted men’s suits onstage, immersing herself in gay culture, coyly hinting that her own sexuality is polymorphous perverse. “I want you all to know that there are only three real men on this stage,” she announced to her fans at one performance. “Me and my two backup girls.”

It’s tempting to regard this sort of transgression as inherently radical: Madonna herself clearly regarded the “Justify My Love” video as something of a political act–a giant “fuck you” to conventional notions of gender and sexuality. But as Marjorie Garber reminds us in her new book, Vested Interests: Cross-Dressing and Cultural Anxiety, gender ambiguity is so unsettling to all conventional notions that it tends to wriggle out of political categories too. A sprawling, fascinating discussion of cross-dressing, transsexualism, and other instances of gender ambiguity, Garber’s book ranges across history and into both high and popular culture–from Shakespeare to Liberace, from Peter Pan to Paris Is Burning.

It’s a subject that’s hard to escape. Gender ambiguity is commonplace in the theater, from Shakespeare’s cross-dressed Viola to the androgynous “Pat” on Saturday Night Live. And it’s pretty common in life as well–from Lord Cornbury, the colonial governor of New York (who dressed as a woman, he said, in order to represent Queen Anne “as faithfully as I can”) to the teenager who wrote recently to an advice columnist inquiring how he could break the news to his girlfriend that “there are times when I would rather wear her panties and pantyhose than my own underwear.” One cross-dressers’ group estimates that 6 percent of Americans are regular cross-dressers; if membership in the Tiffany Club of Waltham, Massachusetts, is any indication, Garber notes, transvestism is especially popular among truck drivers and computer programmers.

The topic of cross-dressing has proved irresistible to academic critics and talk-show hosts alike–on one notable show, Phil Donahue appeared in a dress. “The appeal of cross-dressing is clearly related to its status as a sign of the constructedness of gender categories,” Garber writes. “But,” she continues, setting out what is perhaps the central theme of the book, “the tendency of many critics has been to look through rather than at the cross-dresser, to turn away from a close encounter with the transvestite and to want instead to subsume that figure within one of the two traditional genders. To elide and erase–or to appropriate the transvestite for particular political and critical aims.”

Garber wants to focus instead on the indeterminacies of gender, to explore “the extraordinary power of transvestism to disrupt, expose, and challenge, putting in question the very notion of . . . stable identity.” The cross-dresser is a figure suspended precariously “betwixt and between” the traditional categories–and thus a challenge to all fixed categories. Garber quotes from a French novel of 1835 in which the sexually ambiguous, cross-dressing main character laments that she (he?) has become stuck in between: “Unless I fall in love with some young beau, I shall find it hard to lose this habit, and instead of a woman disguised as a man, I shall look like a man disguised as a woman. In truth, neither sex is really mine . . . I belong to a third sex, a sex apart, which has no name.”

Transvestism shows that sexuality itself is far more complicated than the simple binary oppositions–male and female, gay and straight–we use to structure our understanding of it. Garber argues that transvestism suggests “passing. Trespassing. Border-crossing and border raids.” To the border guards of gender, “this is the scandal of transvestism–that transvestism tells the truth about gender.”

Perhaps the most extraordinary illustration of the cultural anxiety transvestism provokes is the story of the Chevalier d’Eon, “the most famous transvestite in Western history.” D’Eon, who was born in 1728 in France but lived for a time in England, was a prominent diplomat who later in life became an actress, a sexually indeterminate figure who lived 49 years as a man and 34 years as a woman. Garber says that d’Eon existed on the “borderline between genders.”

Anxious and amused speculation surrounded d’Eon throughout his life; indeed, “the London Stock Exchange took bets on his gender.” Eventually King Louis XVI of France demanded that the ambiguity be cleared up once and for all, dispatching an envoy to collect a signed statement from d’Eon him/herself. D’Eon’s response was characteristically ambiguous–s/he declared that there was no ambiguity–and betting resumed at once. Angry bettors finally demanded that the case be taken to court; after hearing from various witnesses, including a surgeon, an English court officially announced that d’Eon was a woman. D’Eon wasn’t entirely pleased with the verdict; Garber notes that she hated “the forced inactivity and the trivial pursuits to which court ladies were restricted.”

The story did not end there. Doctors, friends, and the public at large were startled to learn after d’Eon’s death in 1810 that he was in fact physically a man, complete (the doctor wrote) with “the male organs in every respect perfectly formed.” But, Garber asks, how can a figure so indeterminate be retroactively declared to have “really” been a man? On the basis of d’Eon’s story Garber argues that “the definition of the grounds of human gender will always involve more, and less, than any clearly decidable ‘bottom line.'”

This would seem reasonable enough, but cultural analysts are all too prone to stuff the ambiguities of transvestism into oversimplified accounts that deny or obscure the subject’s complexities. When the jazz musician Billy Tipton died in 1989, he was discovered to have been “really” a woman in drag, hiding her sex from the world and, if we are to believe it, from her wife and adopted children. Everyone, from newspaper reporters to members of the family, attempted to keep the complexities of the situation to a minimum. “He’ll always be Dad to me,” one of Tipton’s sons told the media. The New York Times explained the story as a simple case of economic necessity: in a male-dominated profession, Tipton adopted male drag “to improve her chances of success as a jazz musician.” But as Garber notes, any such simple stories of economic necessity cover over much more than they explain. The couple was said not to engage in sexual intercourse, for example–Tipton told her wife that she had been injured. And clearly it wasn’t “economic necessity” that led Tipton to continue her masquerade in private as well as public life. Like the case of d’Eon, the story of Billy Tipton cannot be reduced to a single unambiguous meaning.

If transvestism unhinges the concept of a stable identity, it also plays havoc with conventional notions of sexuality. Madonna’s video was not the first example of the power of art to evoke “misdirected” lust. With a mixture of horror and fascination, Puritan critics attacked the theatrical cross-dressing that was routine on the Elizabethan stage. “Beware of beautiful boyes transformed into women by putting on their raiment, their features, lookes, and [fashions],” one of these critics warned, “because a woman’s garment being put on a man doth vehemently touch . . . him with the remembrance and imagination of a woman; and the imagination of a thing desirable doth stirr up the desire.” As Garber points out, this writer is describing a “classic . . . fetishistic scenario.” And, I might add, he seems to know what he’s talking about.

Even in our purportedly liberated present, theatrical cross-dressing plays havoc with lust. Garber quotes a revealing interview in which Amy Irving discussed her experience as the “female lead” in the film Yentl, playing against Barbra Streisand’s “male” character. The two shared a bed in a scene that, as Garber notes, “smolders with repressed sexuality.” Irving recalled being “pretty excited” by the experience. “I mean, I’m the first female to have a screen kiss with Barbra Streisand,” she told an interviewer. “[Streisand] refused to rehearse, but after the first take she said, ‘It’s not so bad. It’s like kissing an arm.’ I was a little insulted, because I believed so much that she was a boy that I’d sort of fallen in love with her.” It’s hard to know what to make of all this; Garber doesn’t even try. Is this Irving’s unwitting lesbianism, or a kind of misdirected heterosexuality? Is it a reaction to transvestism itself? None of these explanations seems entirely convincing by itself; perhaps Irving’s reaction was a combination of the three. You could say “only Amy Irving knows for sure,” but I’m not even positive that’s true.

Garber refuses to draw simple lessons; rather she revels in complexity and cultural ambiguities, illuminating her subjects from so many angles that a straightforward summary is impossible. When Garber connects with a subject, this is a fruitful and illuminating strategy. Her language is remarkably clear for an academic study; reading Derrida has not, it seems, permanently impaired her ability to think or write coherently. At times, though, when her brilliance flags, that same ambiguity is frustrating, and the academic tics in her prose become irritating. She sometimes slips into the standard jargon of literary and cultural studies–describing the transvestite at one point as “a signifier and that which signifies the undecidability of signification.” Even more galling, she sometimes falls into the punning that passes for brilliance in much academic literary criticism, talking about “clothes encounters of the third kind” and “the chic of Araby.” In one unforgivable chapter heading she notes that “any way you slice it, it’s still Salome.”

Garber’s inconclusiveness is perhaps a natural choice for a subject steeped in ambiguity; but it’s hard to resist the temptation to pin the subject down, especially when the discussion moves from the cultural to the political. Here Garber’s obscurity becomes truly frustrating. It’s easy enough to find examples of cross-dressing that are as transgressive politically as sexually, but Garber doesn’t go much beyond simply mentioning this fact. She does briefly discuss the drag queens who were at the forefront of the early gay-liberation movement in the late 60s and early 70s, helping to instigate the Stonewall riot in New York that served as an inspiration to the movement nationwide. But Garber never mentions Joan Jett Blakk, the black drag queen and member of Queer Nation who’s running for president. Her candidacy is squarely in this tradition. Blakk, who over the past few years has become a fixture at fund-raisers and demonstrations, uses her flamboyance and campy humor to attract attention to serious political messages–the fight against homophobia, the fight against AIDS. Blakk is unabashedly radical, unabashedly queer; her campaign, as Garber says of drag in general, “institutionalizes the destabilizing gesture.” That’s not something you can say about Bill Clinton. (Though Arnold Schwarzenegger, stumping for Bush, did say that the Democratic candidates were “a bunch of girly-men.”)

Still, the “politics of drag” are not always radical; indeed, sometimes cross-dressers aren’t even political. Garber quotes Oscar Montero, who notes that “drag may be so incorporated into the fabric of society . . . that it ceases to provoke and becomes entertainment.” (And often bad entertainment at that, as anyone can see who’s watched the gargantuan Argentinean comedian Porcel slouch through his drag routines on Channel 44.) In some cases transvestism is identified with the institutions and prerogatives of the elite: witness Harvard’s cross-dressing Hasty Pudding club. A photograph in Garber’s book shows a smiling, lipstick-smeared Clint Eastwood, wearing a flag-bedecked bra over his suit, receiving the Hasty Pudding man-of-the-year award in 1991. I’m not sure how to classify this odd event, but it doesn’t seem to be a step forward.

One reason cross-dressing is not inherently radical is that many of its practitioners still cling to everyday prejudices. Transvestites and transsexuals can be as sexist and homophobic as anyone else. Many male transvestites are, if anything, more anxious to assert their “normal” heterosexuality than other men, to let the world know that they aren’t gay and that their cross-dressing is just a “hobby.” (This tends to be the first question dealt with during talk-show discussions.) At a show by porn-star-turned-performance-artist Annie Sprinkle at Club Lower Links a few years ago, Sprinkle brought out a female-to-male transsexual friend of hers to answer questions about his operation. To the bewilderment of many in the crowd, the new man boasted of his new manhood in terms that sounded suspiciously misogynistic–he liked being a man, basically, because men had more power than women. To a great many of Sprinkle’s impeccably hip fans, I suspect, this was more of a shock than seeing the new man show off his organ–and that caused two audience members to faint.

It’s hard to draw definitive conclusions on a subject so resistant to explanation. Garber shows again and again how those who try to explain transvestism by taming it, stuffing it into some category of “normality,” often simply compound the confusions they hope to erase. Nowhere is this clearer than in the 1953 film Glen or Glenda?, a very low-budget and almost indescribably bizarre attempt to tell the world the simple truths about transvestism. Directed by the “well-known authentic Hollywood transvestite” Edward D. Wood Jr. (who also directed the deliciously awful Plan 9 From Outer Space), it presents with considerable sympathy “the strange case of Glen who was Glenda.”

It’s impossible to convey the surreal charm of this film, which lurches back and forth between the incoherent tirades of a dark and melodramatic Bela Lugosi and the straightforward clinical narrative of the sad life of cross-dressing Glen(da), played by Wood himself. There’s no question that the film is bad–the quasi-scientific narration is filled with lines like “modern man is a hardworking human,” the acting is often below the level of many grade-school plays, and it seems as though half the film consists of stock footage edited in to save a few bucks. But somehow, as Garber notes, the film manages to transcend mere camp; underneath it’s a serious–if gloriously inept–plea for tolerance.

Wood attempts to give his subject an aura of normality. Men turn to cross-dressing, the narrator explains, because male clothing is so rough and uncomfortable–all that wool, and those tight hats that “cut off blood flow to the head.” (Women’s clothes, on the other hand, are nice and comfortable. “Little Miss Female,” the narrator suggests, “you should feel quite proud of the situation.”) It should thus come as no surprise that many “normal” men like to slip into something more comfortable. “Give this man satin undies, a sweater, and a dress, and he’s the happiest individual in the world,” the narrator says of Glen(da). “And he can be more a credit to his community and his government because he’s happy.” Glen(da) is not, the narrator hastens to explain, a “homo sexual”; in fact, “his sex life in all other instances is perfectly normal.” Even “rough, tough individuals” (like construction workers and “your friend the milkman”) like to slip into “pink satin undies” from time to time. As for sex changes–they’re necessary, the narrator argues, simply because “nature makes mistakes.”

But for all the protestations of normality, Glen or Glenda? is one of the strangest films ever made. The more elaborate the explanations (after bodily comfort, the film moves on to the realm of psychoanalysis), the stranger the story becomes. Glen finds himself chased by a “big green dragon” in his dreams; Bela Lugosi, with lightning flashing around him, recites ominous nonsense about “snips and snails and puppy-dog tails.” Even the film’s happy ending–Glen is cured by transferring his feminine fantasies to his fiancee–can’t erase the bizarre effects of the rest of the film. As Garber notes, “slippage and confusion seem to be constitutive rather than accidental features of the attempt to define transvestism.” Perhaps we’d best leave it at that.

Vested Interests: Cross-Dressing and Cultural Anxiety by Marjorie Garber, Routledge, $35.

Art accompanying story in printed newspaper (not available in this archive): illustration/Lisa Michniuk.