It used to be that discussions about gender were as basic and binary as breathing. But in art, theater, literature, film, and more than ever on television (take the critically acclaimed Transparent and other programs now in production), gender identity and expression are all over the map and the notion of gender fixity ever more untenable.

In the early decades of moviemaking, with self-censoring prompted by the industry's Hays Code of 1930 (puritanical restrictions that were particularly stern when it came to sexuality), gender ambiguity was itself coded, addressed as a masquerade in a "straight" romance or as an element of farce. By the end of the 20th century, direct explorations and celebrations—of gender fluidity and gender transition were opening eyes and minds. This fall, for instance, brings the release of The Danish Girl, a movie afoul Lili Elbe, one of the first people in the world to undergo gender-confirmation surgery, starring last year's Oscar winner for best actor, Eddie Redmayne. The movies on this list are all stops along the spectrum between Ozzie and Harriet, masculine and feminine many carrying the period baggage and cliches of those days before audiences had ever heard of the term "transgender." We begin fittingly with Queen Christina, its subject the Swedish royal whose own gender is not quite fixed in history. When Garbo delivers her last line, "The wind is with us," she could be speaking for all who embrace transgender expression and existence as a time-honored fact of life.

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1933
QUEEN CHRISTINA
ROUBEN MAMOULIAN 

Christina, Queen of Sweden, remains a question mark. Historians are still unsure of her sexual orientation, and her gender remains a subject of debate. Reigning from 1644 to 1654, she dressed as a man for much of her life, rode astride, had intimate friendships with women, and refused to marry. Surely the glorious Greta Garbo, herself ambivalent and mysteriously oriented, slipped easily into the role. Cross-dressing with aplomb in this MGM classic and handling the script's implications of bisexuality with a feather-light touch, she seems to be enjoying all the ambiguity. When her advisor barks, "You cannot die an old maid," Garbo responds with brio: "I have no intention to, Chancellor. I shall die a bachelor!"

1935
SYLVIA SCARLETT
GEORGE CUKOR

The first thing she does is cut her hair. Shear the locks, don the suit, add a hat and, voila, Ganymede. The lovely young woman is now a beautiful boy—the kind of boy who gives people, as Brian Aherne says in Sylvia Scarlett, "a queer feeling when I look at you." This ingenue androgyny is unsettling because it's stirring, mercurial. Katharine Hepburn plays Sylvia, who becomes Sylvester to evade the police chasing her and her embezzler father, Edmund Gwenn. Like Garbo, Hepburn wore pants in her private life, so the scene in which she puts a dress back on and relearns how to be female is doubly engaging.

1959
SOME LIKE IT HOT
BILLY WILDER

What a romp! This classic is the gold standard for great escapes into the opposite sex, and both Tony Curtis and Jack Lemmon, who morph into Josephine and Daphne, have a field day. Lrench farce (all those close calls and quick changes) meets vaudeville ( Joe E. Brown showboating effortlessly) as two musicians who witnessed the St. Valentine's Day Massacre skirt murderous masculinity (the Chicago gangsters chasing them) by diving into La Lemme ( the all-girl band into which they disappear). Round and round it goes—with spectacular wit, heart, and physical humor. Where does it stop? Let's just say delightfully at sea.

1975
THE ROCKY HORROR PICTURE SHOW
JIM SHARMAN

Hail the Planet Transsexual (that's 70s-speak) in the galaxy of Transylvania! This orgiastic mash-up of genres—sci-fi and horror films, "rad" rock opera and "trad" musical—was panned by critics (Newsweek would call it "tasteless, plotless, and pointless"). But within a year The Rocky Horror Picture Show rose to cult classic status, and it's been a midnight movie ever since, inspiring fans with the words "don't dream it, be it." An explosion of satin garters and lace-up corsets worn en deshabille, the movie is a good-natured assault on a Ken-and-Barbie world. Tim Curry, as Dr. Frank-N-Furter, is the luminous M.C.

1978
LA CAGE AUX FOLLES
EDOUARD MOLINARO

Just as Renato is celebrating 20 years with Albin, the drama queen of his drag club La Cage Aux Folles, he learns that his son has become engaged to the daughter of a French arch-conservative. Renato and Albin prepare to meet the future in-laws by redecorating monastically and camouflaging (not!) their gay spirits in three-piece suits. One of the most successful foreign films in history, La Cage Aux Folles (which spawned the 1996 feature The Birdcage) was based on Jean Poiret's farce of 1973, as was the 1983 musical of the same name, a Tony-rich hit that contains the gender-fluid anthem of the era. It begins: "I am what I am. I am my own special creation ..."

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1982
VICTOR/VICTORIA
BLAKE EDWARDS

Just seconds into the movie the camera pans from a window to a bed, passing over a photograph of Marlene Dietrich— the queen of nightclub cross-dressing—on the bedside table. Cheekbones for days, you might say, is a top priority of drag, and Victoria ( Julie Andrews) has 'em. Victor/ Victoria is another instance of the escape hatch—this time, escape from poverty— that comes with a drop into the rabbit hole of gender. "A woman pretending to be a man pretending to be a woman," exclaims Victoria, who's been as hungry as Mimi in La Boheme, "it's preposterous." No, it's an adventure in the wonderland of life.

1982
TOOTSIE
SYDNEY POLLACK

A constant of male-to-female transformation, whether its onstage or off, is makeup. If these movies are any evidence, the application of foundations, shadows, lip liners, and wigs has a ceremonial power, a trance-like sensuality. Even Michael Dorsey (Dustin Hoffman), the impossible out-of-work actor who, en travesti, wins a female role in a soap opera, is deeply involved in his maquillage. Each stroke of the mink-bristle brush takes him further into another world—the truth of Dorothy Michaels. Playing a woman, he tells his playwright friend Jeff, "happens to be one of the great acting challenges." Creating her enlarges him—and helps the audience confront its own gender biases and assumptions.

1990
PARIS IS RURNING
JENNIE LIVINGSTON

What Livingston's documentary came out in 1990 most Americans had no clue about "ball culture" or the shadow meanings of its vocabulary: terms like "house," "walk," "realness," "shade," and "voguing" (this last went mainstream pretty quickly thanks to zeitgeisters Malcolm McLaren and Madonna). Balls are street-smart competitions held in ballrooms (or big rooms) in which black and Hispanic men—gay, bi, trans—emulate high-style icons in cheeky catwalk performances. A convergence of empty pockets and wild imagination, ambition and appropriation, a drive to belong and a history of rejection, ball culture may focus on "la mode" but its participants bum, poignantly, for a small piece of the American Dream. That said, there have been recent and contentious protests about the movie over the way homeless trans people, on-screen, have been depicted and treated.

1992
THE CRYING GAME
NEIL JORDAN

"Who knows the secrets of the human heart?," a bartender asks philosophically. Such secrets provide the undercurrent of this psychological thriller from Neil Jordan. It opens with an IRA kidnapping gone bad. Fergus (Stephen Rea), who'd grown close to the hostage, Jody (Forest Whitaker), survives the debacle yet keeps seeing Jody in his dreams. He's haunted by guilt and perhaps something more enigmatic. Having promised to look after Jody's girlfriend, Dil (Jaye Davidson), Fergus finds himself again drawn to someone against his will. Is this weakness or strength or both? Whatever it is, as Jody said to Fergus, "It's in your nature."

1992
ORLANDO
SALLY POTTER

A costume drama without the drama, or, rather, the drama's in the imagery-compositions that evoke Renaissance art, Elizabethan portraiture, and paintings Romantic, Pre-Raphaelite, Orientalist—this beautiful movie rides from century to century in Tilda Swinton's wondering eyes, their color changing with the epochs. In the film based on Virginia Woolf's satirical novel of 1928, Orlando is a young lord who not only doesn't age, he changes (while sleeping) from male to female. "Same person, no difference at all," the newly minted Lady Orlando says with British dispatch. "Just a different sex." She's speaking for Woolf, who's speaking for detente between the genders.

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1993
FAREWELL MY CONCUBINE
CHEN KAIGE

Two boys, Shitou (Fengyi Zhang) and Douzi (Leslie Cheung), grow up together in the strict, often sadistic school of the Beijing opera—China's highly stylized, colorfully kinetic, all-male traditional theater. They become famous in roles they were trained for: the King and his Concubine in the opera for which this movie is named. But where Shitou is pragmatic, embracing stardom and marrying breezily, Douzi, the artist of the two, cannot or will not separate life from art. He carries the Concubine's devotion offstage, becoming jealously possessive of Shitou. Set against the eruptions and revolutions of 20th-century China, the relationship of these two troupers is violently tested. For Douzi, consummation comes only and finally in costume.

1994
THE ADVENTURES OF PRISCILLA, QUEEN OF THE DESERT
STEPHAN ELLIOTT

A road movie. But instead of Hope and Crosby (who did their fair share of drag) it's two queens, Tick/"Mitzi" and Adam/ "Felicia" (Hugo Weaving and Guy Pearce), and transgender Bernadette (Terence Stamp). In an old bus christened Priscilla they make their way through the Australian outback for Alice Springs, a gig at a resort run by the wife Tick never divorced. One can't make great claims for the hokey-pokey act of this lip-synching trio, but their flamboyance— Cirque du Soleil on estrogen—is a litmus test of tolerance in towns along the way. And Stamp, with his lordly line readings and pure calm, is our unlikely Lady of the Wayside.

1997
MA VIE EN ROSE
ALAIN BERLINER

A flower of a performance blooms delicately at the quick of this unforgettable movie, that of young Georges Du Fresne as "Ludo." A seven-year-old boy who calls himself "a girlboy," he tries again and again—through dress, through fantasy—to become female. He believes (with remarkable sophistication) that he's a scientific error, God having mistakenly dropped his second X chromosome. "But God'll fix it," Ludo says. "He'll send me my X." Ludo's certainty about his gender upsets the status quo, unbalances the adults. Today, 18 years after the film's release, we understand that Ludo was right: Nature works in cryptic ways. And we have learned to compensate for that missing X or Y

1999
BOYS DON'T CRY
KIMBERLY PEIRCE

The first thing we see are his eyes in the rear-view mirror—bright, excited, he's living it, passing for a man. As Brandon Teena (and at times, Teena Brandon), Hilary Swank is as clean as a new dime. Brandon wears plaid flannel shirts and stuffs a rolled sock in his jeans. Watching him spar with the guys in their dominance hierarchy is terrifying; boy, what guts. But with no money to transition, it's a joy ride in a dream. Girlfriend Lana (Chloe Sevigny) doesn't need Brandon to be anything more than himself, but that's not good enough for anyone else, including Brandon. The role brought newcomer Swank an Oscar for best actress. (See page 86 for John Gregory Dunne's account)

2001
HEDWIG AND THE ANGRY INCH
JOHN CAMERON MITCHELL 

Musical memoir (with a whiff of mockumentary), graphic novel, rock opera —Hedwig and the Angry Inch is all these genres rolled into one big creation myth, a ferocious riff on the meaning of wholeness, loss, and love. Ever since Hansel/ Hedwig suffered a botched surgery, this "slip of a girly boy from communist East Berlin" has been in gender-identity limbo. It's unclear where Hedwig is by movie's end— Mitchell calls her "genderqueer"—but an artistic transfiguration has occurred and a measure of metaphysical wholeness achieved. The film is based on Mitchell's off-Broadway hit of 1998—now in revival on Broadway.

2004
BEAUTIFUL BOXER
EKACHAI UEKRONGTHAM

A classic fight movie, but the fight here is for beauty. Turning the martial arts genre on its ear, this elegant biopic from Thailand tells the true story of Parinya Charoenphol, a transgender champion kick boxer. As a boy, it is his glimpse of an exquisite actress in full makeup that answers the question of his destiny. Fate leads him to boxing camp and though fighting offends him, its formal beauty is inspiring. Parinya (Asanee Suwan) begins to wear make-up in the ring and while some call it a gimmick, the boxer is moving toward a truer self and the "quiet heart" that comes with it. As gender-confirmation surgery approaches, Parinya says, "I can't live until I die in this body."

2005
TRANSAMERICA
DUNCAN TUCKER

It's one week until "Bree" (Felicity Huffman), formerly Stanley Schupak, will receive her long-awaited sex reassignment surgery, so it's a badly timed bolt from the blue when the phone rings and a boy named Toby (Kevin Zegers), 17 years old, says he's looking for his father Stanley. Bree's therapist won't sign off on the surgery until Bree acknowledges her son as a part of her life. She heads to New York City to bail him out of jail and thus begins another road movie—an unusually gentle one despite Toby's feral behavior. While he hoped to find a rich father in a fancy mansion, he got something better: a mother who understands all.

2011
ALBERT NOBBS
RODRIGO GARCIA

"Such a kind little man," a guest at Morrison's Hotel says of Albert Nobbs, one of the hotel waiters. "I think you are the strangest man I ever met," says Helen, the hotel maid that Nobbs is trying to court. Kind, strange, introverted, inexperienced, Nobbs is not a man, but a woman (Glenn Close) who was abandoned as a child, then gang-raped at the age of 14. To hide, to survive in Victorian-era Ireland, she buys a black suit and bowler and loses herself in service, precise and correct, yet a mystery. Who, now, is inside that suit? Not even Nobbs, one senses, has the answer.

2011
TOMBOY
CELINE SCIAMMA 

Laure (Zoe Heran) is a 10-year-old French girl of few words. She wears her hair short and hovers in that moment before puberty, when a girl can be as lean as a classical kouros. The family has just moved and Faure introduces herself to the neighborhood kids as Mikael. Watchful, wary, she's the most beautiful of the boys—a young David. Playing soccer, going bare-chested like the others, Mikael is elated, alive, a puzzle piece finally locking into the picture. But when Mikael fights with another boy, his mother comes calling and the jig is up. Director Sciamma wraps the loss of Laure's idyll in sighs and silence. The isolation is deafening.

2013
DALLAS BUYERS CLUB
JEAN-MARC VALLEE

It's so hard going back to those years, back to the 1980s and those first deaths from an unnamed disease, back to the last-gasp years before the mid-nineties, when the "AIDS cocktail" of protease inhibitors (for those fortunate enough to have the medical care and the funds) promised to eventually remove the word "terminal" from the diagnosis. For those too young to have known that era, Dallas Buyers Club is a clinical view of an equal-opportunity horror. It's 1985. The homophobic rodeo tough Ron (Matthew McConaughey) and the drug-addicted transgender beauty Rayon (Jared Leto), both HIV-positive, team up to import alternate drug therapies. Foxhole buddies in a then unwinnable war, both fight to the end, equals in valor. Both actors received Oscars, but many in the trans community have used the film as an opportunity to point out that there are too few movie roles for trans actors.

2015
TANGERINE
SEAN BAKER

Shot, incredibly, on three iPhone 5s, Tangerine is a low-budget treatment of a classic trope: a day on the street, fates intersecting like crosswalks. And not just any street, but a Hollywood strip where transgender prostitutes ply their trade. Sin-Dee Rella (Kitana Kiki Rodriguez) has just been sprung from 28 days in jail, and her best bud Alexandra (Mya Taylor) lets slip that Sin-Dee's boyfriend-pimp, Chester (James Ransone), has been sleeping with a white girl, "vagina and everything!" It's not to be borne, and Sin-Dee's on a mission to confront. In Baker's hands the dark side of life on the street gives way to something sweeter, the "little girl and boy land" of the movie's opening melody, "Toyland."