Critic's Notebook: Hollywood's Trans Journey, from 'Crying Game' to Caitlyn Jenner

Eddie Redmayne in 'The Danish Girl,' Kitana Kiki Rodriguez in 'Tangerine' and Laverne Cox in 'Orange is the New Black'

Caitlyn Jenner's conquest of the cultural mainstream comes on the heels of a long — and sometimes laudable — history of transgender representation in movies and TV.

A version of this story first appears in the June 26 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

With the June 1 release of her Vanity Fair cover, the butterfly known to the world as Caitlyn Jenner emerged from the chrysalis of former Olympic athlete Bruce. That arrival has been embraced with the kind of overwhelming public approval that would have seemed unimaginable a decade ago, when some conservatives still felt entitled to slur the LGBT community without fear of reprisal. Now, even cultural troglodytes are tripping over themselves to get the pronouns right.

The "Caitlyn moment" also coincides with unprecedented visibility for transgender characters in film and TV. Teens struggling with gender-identity issues these days don’t have to look far for empowering role models of every stripe, even if few of them sugarcoat the challenges. And while there are inevitable arguments over authenticity as well as artistry, those challenges recently have been portrayed with surprising sympathy and nuance on both big and small screens.

Jared Leto won an Oscar in 2014 as the fragile but beautiful Rayon, a sweet-souled transgender woman dying of AIDS, in Dallas Buyers Club. Jeffrey Tambor picked up a Golden Globe this year for the dignified forbearance and gentle humor he brought to a middle-aged man navigating both his new life as a woman and his neurotic family in Amazon’s Transparent. Transgender actress Laverne Cox became a breakout star of Netflix’s recently returned Orange Is the New Black playing prison inmate Sophia, whose struggles to connect with her young son and keep up with hormone therapy in the face of corrupt health-care cutbacks have been among the series’ most affecting arcs. Meanwhile, Eddie Redmayne is following his best actor Oscar win this year by playing transgender artist Lili Elbe in Tom Hooper’s upcoming The Danish Girl — another role that puts him on the (admittedly premature) award frontrunner roster.

In the more immediate future, moviegoers can check out one of the highlights of this year’s Sundance Film Festival: Sean Baker's microbudget indie Tangerine (out July 10), which chronicles the all-night odyssey of a fierce banshee hunting the biologically female rival who muscled in on her man. What's most notable about the film is not that it's about black transgender prostitutes on the skuzzy streets of L.A., but that it's a funny, big-hearted girlfriend movie — no less warm and accessible than Bridesmaids, even if it won’t garner the same love at the box office (we haven’t come that far).

Non-narrative treatment of the "trans" experience also is becoming part of the TV landscape. In addition to I Am Cait, the upcoming E! docuseries in which Jenner explores her "new normal," ABC Family just debuted Becoming Us, a sensitive look at a 17-year-old whose father becomes a woman.

Indeed, gender metamorphosis today neither is a punchline, as on the classic 2005 South Park episode "Mr. Garrison's Fancy New Vagina," nor a font of freakish evil, as with the murderers played by Michael Caine and Ted Levine in Brian De Palma’s Dressed to Kill (1980) and Jonathan Demme’s The Silence of the Lambs (1991), respectively. Though activists who bristled at such negative stereotypes were on the right side of history, I hate to think of an industry so intimidated by PC concerns that those vividly cinematic, if representationally irresponsible, pleasures would be denied us. The ideal scenario, of course, is a world in which trans characters are such an accepted part of the cultural fabric that any and all of them, from saints to serial killers, can be depicted without watchdogs barking.

We may not be there yet, but the fact is that groundwork has been laid via the transgender characters who have been right under our noses in our movies and on our TV sets for decades. And while pundits love to — often rightly — slam Hollywood for lagging behind the diversity curve, many of those portrayals have been bracingly unpatronizing, ranging from the low-key (Karen Black in 1982’s Come Back to the 5 & Dime, Jimmy Dean, Jimmy Dean or Glenn Close and Janet McTeer in 2011's Albert Nobbs) to the defiantly glamazon (John Cameron Mitchell in 2001’s Hedwig and the Angry Inch or Terence Stamp in 1994's The Adventures of Priscilla, Queen of the Desert).

Sidney Lumet’s Dog Day Afternoon (1975) remains a milestone for its clear-eyed depiction of the love between Al Pacino’s bank robber and his pre-operative transgender wife (Chris Sarandon). John Lithgow played a sort of precursor to Jenner in 1982’s The World According to Garp, impeccably understated as a transgender former football star. The integrity Hilary Swank brought to her performance as small-town trans man — and murder victim — Brandon Teena in 1999’s fact-based Boys Don’t Cry earned the then-little-known actress an Oscar. And Felicity Huffman’s empathetic turn as a pre-operative transgender woman who learns she has a son made it easy to overlook the rough edges of 2005’s Transamerica.

One of the most indelible transgender screen roles remains Jaye Davidson’s character in 1992’s The Crying Game: a London hairdresser who becomes involved with the former IRA terrorist who captured her British boyfriend. The actor’s subtle, deeply felt performance breathed humanity into what could have been a mere narrative gimmick. (It’s inconceivable in these days of instant viral sensations that any company could be as successful as Miramax was at the time in keeping that surprise penis under wraps.)

TV arguably has been even more integral in nudging the needle with mainstream exposure to transgender characters played — for largely inoffensive laughs, poignancy or even mystery — by Lisa Edelstein in Ally McBeal, Kathleen Turner in Friends, Rebecca Romijn in Ugly Betty, Dot Marie Jones in Glee and Olympia Dukakis, so wisely wonderful in Tales of the City.

Arguably, no major filmmaker has shown more love for transgender characters than Spain’s Pedro Almodovar, in films including Law of Desire, All About My Mother, Bad Education and, more perversely, The Skin I Live In — all of which garnered significant critical attention and sizable art house followings stateside. His transgender women are seductive and soulful, campy at times but always real.

Just as black presidents in popular films and TV shows from Deep Impact to 24 familiarized a pre-Obama America with the once-unthinkable notion of an African-American commander in chief, this ever-growing panoply of transgender characters has helped open narrow minds and foster understanding over fear.

Has Caitlyn Jenner achieved even more than that with one widely watched ABC interview and a glossy magazine shoot? Perhaps. Certainly, her emergence has had a far more pervasive impact than when Chaz Bono went public as a man five years ago. However, as Cox wrote after Jenner’s Vanity Fair spread appeared, relatively few trans people have the advantages that wealth and celebrity provide. That means safe, supportive environments — but on a more cosmetic level, it means the best stylists, makeup artists, hairdressers and surgeons, not to mention Annie Leibovitz to shoot their portrait. For that very reason, we should be as eager to salute Tangerine’s scrappy Sin-Dee Rella and Alexandra, played by glorious transgender actresses Mya Taylor and Kitana Kiki Rodriguez, as we are Caitlyn.