I fell in love with Julie Andrews when she punched a hustler while coming out a closet dressed in a suit.

The symbolism couldn’t’ve been more obvious. But Victor/Victoria (1982) is more than a “gay romp” where a woman impersonates a man who impersonates women. Her portrayal had nothing to do with macho swagger (“Count Victor” is a homosexual drag queen).

Yet Andrews walks, talks, and exists as Victor in ways she isn’t Victoria. Victor’s vanity and style are classy; if they’d been Victoria’s vanity and style, they’d be frivolous. It’s how she hits the hustler, knuckles out, not afraid of breaking nails. She knocks him backwards, ass over tit. The attacker flees.

Julie Andrews doesn’t resemble a man. She doesn’t mock “masculine” mannerisms. Victor studies impacts of gender on social interactions. Victor can be who Victoria’s always wanted to. But is she reaping the benefits of being a man? What’s wrong with that?

I fell in love with Tim Curry when I realized how macho he was while strutting his stuff as Dr. Frankenfurter in The Rocky Horror Picture Show (1975). It was how Curry walked and talked. Curry swaggers with macho confidence in heels. His comebacks are thrown back with just enough queenly flair. He’s irresistible to the eye. His performance falls squarely between campy, satirical, and grotesque. Rocky is the most cult of all queer cult films.

America’s in love with Ru Paul’s Drag Race, Pose, and Euphoria. It seems America agrees: there can be transgender actors and characters in popular television shows, and the once niche, cabaret-styled, gender-bending art known as drag has become mainstream entertainment.

(It’s impossible to discuss drag and crossdressing without discussing trans characters in the same breath.)

But drag continues to be divisive. Maybe it should.

Drag and crossdressing serve many purposes in film. Some filmmakers use drag and crossdressing to mock queer identities or use drag as a joke. Others use drag to celebrate queer, trans, and other identities. But directors aren’t of one mind what it means to celebrate queer identities.

Should drag be divisive? That depends on the drag act.

Candy Darling of Andy Warhol/Paul Morrisey fame fit the image of a “celebrity” drag impersonator. She resembled Kim Novak. This is typical of familiar “female celebrity impersonation” drag acts.

Drag culture often pays homage to drag cultural history. That’s why popular drag characters include: Marlene Dietrich as Amy Jolly in Morocco (1930), where she cross-dresses in a tux, tails and top hat; Gloria Swanson as Norma Desmond in Sunset Boulevard (1950), where she impersonates Charles Chaplin; and Liza Minelli as Sally Bowles in Cabaret (1972), the iconic image of cabaret performers casual audiences recognize. Even the host of the Kit Kat Club’s festivities is a classy/sleazy gender-bending character, and their image appears in drag acts frequently. Candy Darling’s homage to Kim Novak is typical of drag.

Divine, who became infamous for his outrageous persona in John Waters films, couldn’t’ve been farther from the image of traditional feminine grace, beauty, and eroticism.

Warhol’s films emulate glamourous Hollywood imagery, which he subverts. Waters’ films do away with glamourous imagery altogether and are an affront to all beauty standards.

Darling and Divine usurped traditional gender standards, but Waters’ approach is divisive: his films don’t only usurp traditional gender roles, but all aesthetics. Warhol and Waters utilized experimental film making. Their films challenge narrative conventions.

When watching films from both directors, I ask: do these films exist in separatist queer worlds? If so, drag is divisive.

Some crossdressing characters defy definition. Whether they celebrate or mock queers is up to interpretation.

In The Boondock Saints (1999), FBI agent Paul Smecker isn’t flamboyantly gay, but not closeted. Paul’s campy in manipulative way which undercuts macho, homophobic cop culture. Agents and cops expect him to act effeminately. They’re surprised by his abrasive personality. Why does Smecker disguise himself in drag as a prostitute to defend the McMannus brothers? He could’ve disguised himself as anything. A crossdressing Willem Dafoe isn’t feminine, especially while exterminating mafia hitmen. But it’s right. Smecker’s image reminds me of Pris from Blade Runner (1982), who is equally terrifying when she attacks, then is killed by, Rick Deckard.

When I watch M. Butterfly (1995), I sense but don’t fully grasp its cultural relevance. Song’s gender identity is performance, but it’s elegant and dignified. Song isn’t deviant. The only role that comes close to echoing its resonance is Sam Rockwell’s portrayal of Francis Flute/Thisby in A Midsummer Night’s Dream (1999). But Gallimard’s speech (impersonating Song’s female impersonation) before his suicide is layered with meaning. It’s melodramatic, but it stretches towards Jungian overtones before its bloody end.

Drag, crossdressing and trans/queer identities are often mentioned in the same breath; it should be no surprise filmmakers handle these issues with varying degrees of conflation or understanding.

It may surprise readers that one of the first films about queer rights argued for them. Different from the Others (1919) is a German film which condemned Paragraph 175, the German law which outlawed homosexuality. Paul and Kurt, two violin virtuosos, suffer from social pressure, blackmail, and public outing of their orientation and relationship. Their families misunderstand. A medical professional provides information about homosexuality, transsexuality, lesbianism, and gender identity, arguing they are biologically predetermined, not psychiatric conditions, sins or crimes. Their families begin accepting and understanding. Paul commits suicide when pressure becomes too great. The film advocates for an end to Paragraph 175.

And in a way, Different was almost a century before its time.

In the current edition of the DSM, the manual recognized as a psychiatric diagnostic standard, for crossdressing to be a mental health concern, individuals must be sexually aroused by crossdressing, and crossdressing must distress patients or disrupt their lives. Unless both conditions are met, it’s not considered a medical concern. However, this was the definition in 2013.

Still, many films portray crossdressing as a symptom of a diagnosable condition. Psycho (1960) used Norman’s appearance as “mother” to conflate crossdressing with split personality. If “mother” is the dominant personality, why doesn’t she dress as herself then occasionally dress as her son? Why do the personalities change clothing? The explanation is likely Robert Bloch’s novel, which drew inspiration from Ed Gein’s crimes, included evidence of Gein’s necrophilic crossdressing. Psycho reflected professional psychiatric misunderstandings in 1960; crossdressing was considered a sign of mental illness, so Psycho conflates crossdressing with split personalities.

Other films don’t have ready excuses for misusing diagnoses.

Insidious Chapter 2 (2013) exploited previous diagnostic standards by portraying its antagonist, Parker Crane, as a crossdresser. Why’d Crane become the Bride in Black? His abusive mother dressed him as a girl. It draws an oft-repeated but overly simplistic conclusion: victims become predators. The film could’ve pondered if Crane murdered women who remind him of his mother, or if he’s imitating his mother like Norman in Psycho, but Insidious doesn’t address this nuance. Insidious utilizes both an outdated diagnosis (crossdressing as a symptom of mental illness) and the myth of generational “curse” passed from abuser to victim (indicating psychiatric conditions are caused by trauma). The answer can’t be both. It breaks down logically.

  1. Night Shyamalan should’ve considered Insidious’ failures before he wrote and directed Split (2016), but that’s the least of Split’s problems.

Of course, pro-LGBTQ films can make the same mistake in misdiagnosing or conflating fetishism with transgender identities.

The Danish Girl (2015) did, which is a shame, considering Lili Elbe was a recipient of one of the earliest gender reassignment surgeries who tragically died during the second procedure. Elbe had had a sense of her identity before she even met her wife, and before her wife asked her to pose in women’s clothing. The film squandered an opportunity to represent Elbe’s true identity while seemingly representing a transwoman character onscreen.

There’s no point dissecting Sleepaway Camp (1983); what could’ve been a competent teen slasher ends sadly on a horror-themed penis joke. There’s sexual tension in Sleepaway that’s never delivered, so we ponder its presence, until the end. We should be frightened that Angela brutally savaged her bullies. Why anyone thought the shot of Angela, nude, covered with blood, with male genitalia was a good conclusion is beyond comprehension.

I’ve tried to enjoy The Crying Game (1993). But the way Dil reveals her trans status sets us up for Fergus to punch her. Dil forgives after a heartfelt letter. Dil has no reason to want Fergus other than the fact he was kind to Jody when Jody was captured by the IRA (Jody’s killed anyways). Fergus is ordered to murder Dil, but doesn’t follow through. Why’s Dil want him? It seems there’s an assumption Dil accepts any sexual attraction, affection, love, or friendship she’s offered because she’s trans. That’s an ugly assumption, and it feels so flippantly assumed.

Buffalo Bill from The Silence of the Lambs (1991) complicates definitions on what is and what isn’t a misuse of diagnoses. Bill’s supposedly not trans, though they believe they are. They seek violent sexual thrills; they want to make a suit of women’s skins. This opinion comes from Hannibal Lecter, whose opinion is dubious. What’s divisive about Jame Gumm/Buffalo Bill is Silence doesn’t state whether Jamie/Bill is a transwoman or fetishist. It shouldn’t matter. Whether or not Jaime/Bill is a woman, Katherine Martin’s in a hole in their basement. Unless Clarice intervenes, she’ll be cut up for Bill’s suit.

Clearly, Silence learned lessons from similar films portraying psychotic doctors. Silence is superior to Dressed to Kill (1983). I could never determine which side of the “split personality” (crossdressing seems often used to portray that), Dr. Elliot or Bobbi, was killing, since they shared a hatred of women.

This being said, some films study the relationship between crossdressing, identity, and trauma.

The Skin I Live In (2011) is a twisted drama where revenge, disfigurement, medical abuse, rape, drugs, mental illness, murder, and assault are typical. One character forcefully undergoes sex change reassignment as part of their incarceration and abuse, then becomes perplexed on their identity. Character’s identities morph under pressure. Skin is potentially the most complex film exploring the relationship between gender identity, psychological manipulation and sexual fetishes. The riskiest fetish is control.

Another notable example is The Tenant (1976). In Polanski’s paranoia-inducing flick, Trelkovsky’s driven to paranoid delusions in a claustrophobic apartment in a building populated by aggressive, complaining tenants. Every noise echoes through the building. Cultish tenants constantly feud. The former tenant, Simone Choule, killed herself by jumping from the window. Strangers make subtle comparisons between Choule and Trelkovsky. He feels driven into her psychological state. Trelkovsky’s crossdressing is a histrionic symptom caused by the hostile environment. When he dresses in a sundress, wig, nylons, garters, platform heels and bold makeup, then imitates a theatrically feminine voice to himself in a mirror, we’re not disgusted by his appearance, we’re scared for his sanity.

(After re-watching Tenant, I wonder if anyone sensed Polanski’s instability. I can’t stop thinking his infamous pedophilic sex crime occurred a year after filming.)

Some comedy films utilize crossdressing or drag as a comedic trope. It shouldn’t surprise us it does: cabaret and burlesque, the godmother and godfather of drag, make regular use of erotic humor. But these comedic tropes can backfire.

In Some Like it Hot (1959), Joe and Jerry cross-dress to escape danger. But Hot is problematic when Jerry/Daphne potentially develops attraction for Osgood. Jerry’s more attracted to Osgood’s attention and pampering than to Osgood himself. When Jerry admits he’s a man, Osgood says “well, nobody’s perfect.” If this weren’t the last line of the film, it might mean Osgood’s curious about Jerry’s attraction. But the line works as a laugh line. It mocks such possibility.

Other films make crossdressing the central joke when other issues could be addressed.

Mrs. Doubtfire (1993) could make a bigger point about men’s custody rights and unequal demands courts make on husbands in divorce cases. It loses sight of its conflict when Doubtfire becomes larger than Daniel. Doubtfire’s thesis is that the system needs not be changed nor challenged and men need to rise to its extreme demands. This message is escapist and damaging.

The joke doesn’t have to be classy to take advantage of this trope, and these are rarely in good spirits.

Ace Ventura: Pet Detective (1994) would’ve been low brow, hyperactive humor if it hadn’t been for the final scenes. There’s no need to strip Lois Einhorne and reveal she’d not gotten a penectomy or vaginoplasty. Showing this onscreen is just distasteful and insensitive for humor’s sake, and while it need not be banned, it’s truly unnecessary vulgarity.

There’s no reason why Roger wears a gown in The Producers (1967 or 2005). Roger’s gay, campy and absurd, but his melodramatic actions and ineptitude are funny, not his dress. It plays to the stereotype that gay men wear flamboyant clothing, but Roger’s assistant, Carmen Ghia, is just as stereotypically gay yet dresses normally. Rogers’s dress is a barely a joke (and not a good one), then doesn’t have a further point.

Other films seem to self-satirize queer identities when they could be better addressed.

Glen or Glenda? (1953) wants to address the real needs of crossdressers and make sure their identities are distinct from homosexuals. But it descends to condemning and shedding mockery on crossdressers. Patrick/Patricia commits suicide in Glenda. What I gather from Glenda (it’s a bad film, that’s why it’s a cult film today) is it advocates for the rights of crossdressers while still reflecting biases of its time.

Even films with best intentions can fall back on using drag acts to provoke shock and titillation.

Marlene Dietrich’s appearance in Morocco (1930) was groundbreaking for its time. Dietrich was not truly impersonating her wealthier lover, but mocking him. She retains her feminine sexuality while performing as a drag king. The kiss she gives the female cabaret patron (in front of the patron’s husband) is an act of titillation. Memorable as Dietrich’s appearance is, Amy’s kiss is a naughty joke with no impact on Morocco.

And some films I’m torn upon.

It’s sad that Boys Don’t Cry (1999) is the film version of Brandon Teena story, because Teena’s death was the result of a heinous transphobic crime against a transgendered teenager. I want to see Boys as revolutionary. But all the characters act in self-sabotaging ways. There’s been much analysis written about Boys. Boys might be more nuanced than I know. But Boys sacrifices Brandon, Lana, and Candace as queer cannon fodder. They rarely learn lessons. They make decisions against their own survival. They suffer, die or both.

So which trans, crossdressing, and drag films are worth watching? I can only address a few examples.

As discussed above, Cabaret, Tenant, Skin, Victoria, Morocco, Rocky, and despite their complexities, Boondock, Silence, Psycho, Butterfly, and Hot. I’ll throw in Midsummer, which is arguably just a good film.

Andy Warhol, John Waters, Kenneth Anger, and Derek Jarman films are standards. Their techniques and approaches to their subject matter vary, and some seem to posit a separatist, escapist, all-queer world, but they don’t fundamentally demean queers, even in pursuit of divisive, disruptive humor.

Kinky Boots (2005) delivers lighthearted fun and provides socioeconomic critique. A failing shoe company is revitalized when its innovative owner, Charlie, realizes drag queens need larger, durable platform boots. It doesn’t avoid awkward moments between flamboyant queens and stodgy British laborers. Charlie risks his money, his engagement, and even walks the catwalk in heels to protect jobs for his employees. That’s a hero.

I never knew I needed Hedwig and the Angry Inch (2001) ‘til I saw it. Hansel, a rock-and-roll loving queer teen, is desperate to escape East Germany. An American soldier proposes marriage. Hansel becomes Hedwig via an imperfect gender reassignment surgery leaving an inch of unwanted genitalia. The wall falls anyways. The soldier leaves Hedwig. Hedwig starts a rock-and-roll band, finds fame, has lyrics stolen by her queer protégé. She might’ve never had surgery. There’s Greek philosophy in Hedwig. Hedwig’s a Greek tragedy queer rock opera. Everybody should watch it. This film could easily dethrone Rocky as the new alt-queer film (but not quite yet).

Rent (2005) is a throwaway choice, but the only reason I think this is because the queer community has touted it so often. It’s worth a watch just to investigate why it has become such a staple of modern queer culture. If anything could be a bigger new alt-queer classic than Hedwig, its Rent.

Texas Buyer’s Club (2013) afforded dignity and respect to Rayon, a HIV-infected, drug-addicted transwoman who helps Woodroof run an illegal market exchange for underground drugs treatments for HIV patients. Texas doesn’t shy from difficult questions about wealth, power, bias, and privilege around healthcare in America. Rayon helps him challenge transphobic, homophobic beliefs. Jared Leto studied with transgender actresses and never broke character throughout filming. I admire that.

Stardust (2007) is a gratefully complex, nuanced and dark children’s fantasy film. Its most lighthearted scenes are of Captain Shakespeare, a crossdressing pirate captain who struts about in pink lingerie while dancing Antonin Dvorak’s compositions. Robert De Niro’s humor references classic Venetian carnival cross dressing costume and shenanigans pretty perfectly, and somehow the whole chemistry just fits.

Transamerica (2005) is really a mediocre film and queer family drama, but it contained moments of honesty about choices trans people make considering their medical options, which I hadn’t seen featured in film before. I didn’t expect the inclusion of these scenes, but they shed light on the variety of medical decisions trans people make while transitioning.

I find, ultimately, that there is still much wanting in terms of representation for trans people, crossdressers, and drag performers in film. I’m reminded how vastly representation has improved. I believe in the future, respectful portrayals will be common. And secretly, I hope portrayals never becomes too tame: cabaret and burlesque didn’t pay performers by playing safe.