Over the past 70 years, Americans have moved through countless cultural shifts

focusing on gender, race, sexual orientation, and gender identity, many of which were spurred
by media. Following World War II, as mass media became more and more prevalent in
American’s lives, our perspectives and beliefs were increasingly informed by what we
consumed, and vice versa. Beacuse of this, examining media trends can serve as a bellwether
to measure change over time on ideas like transgender identity.
In this paper I analyze various trends in American media to gain a better understanding
of the aesthetics and understanding of trans identities throughout time, starting with drag
comedies of the postwar era, moving into horror films of the 1970s and ‘80s, a transitional
period in the ‘90s and ‘00s, and finally the more complex debates of the 2010s. While these
trends are not constrained by the time periods mentioned, they can be considered key periods
in which the shifts passed into the mainstream. Overall, this analysis charts a shift in attitude
towards trans people from comedy to a more nuanced attempt at understanding of this identity.

A “necessary” deception
Starting in the 1950s, in the time of true mass media with the onset of widely available
television and increased movie theater attendance, a clear narrative for crossdressing and
transgender stories forms. During this postwar period, the majority of trans-focused narratives
were implicative, and focused more on men forced into awkward circumstances rather than any
genuine identity crisis.
The most well-known iteration of this theme is the 1959 film ​Some Like It Hot, ​in which
two men are forced into hiding after witnessing a Mafia killing, and their chosen disguise is as
women. As is often the style of these early-period crossdressing narratives, there’s no real
connection or acknowledgement of those with true transgender identities, but the humor is
mined purely from the misadventures and misunderstandings of two men successfully
masquerading as women. One of the most iconic lines of cinema comes from when, at the end
of the film, Jack Lemmon, dressed as a woman, is trying to dissuade Osgood from romantically
pursuing him. He offers reason after reason for why he would make a bad partner. Exasperated,
Lemmon gives up, removes his wig, and defeatedly exclaims “I’m a man!” Osgood plainly
responds, “Nobody’s perfect!”

https://www.youtube.com/watch?v=-mHhr-aaLnI
Some Like It Hot

This line perfectly encapsulates the relative innocence of these aesthetic narratives of
the time. It’s an oddly progressive sentiment — that no matter what your status, love is love.
Though it may not have been intended quite that generously when it was written, compared to
much of the more pernicious media that would follow, it’s a hopeful tone to set.
This ending is an example of a common theme throughout most plots involving a man
disguised as a woman. Almost inevitably, some other man will unwittingly express attraction to
the crossdresser, often pursuing her aggressively. In many ways, this is also a progressive
subversion of normal gender dynamics in mainstream American media. Rather than being
charming, the aggressive courting tactics of midcentury America are turned to comedic horror as
man pursues man. It offers a critique of men’s objectification of women, while also
commodifying transgender aesthetics and exploiting gay panic as a source of comedy. The idea
of simultaneously progressive and regressive art is a regular one in crossdressing and
transgender narratives. With each stride forward in representation, there are new problems to
address.
This tradition of innocent crossdressing used for comedy can be seen in clear
descendant series ​Bosom Buddies (​ 1980-1982), which stars Tom Hanks and Peter Scolari as
two men, broke and looking for a place to live, that find an all-women’s building and are forced
to live dual lives to maintain their living situation. Similar to ​Some Like It Hot​ two decades
earlier, the drag in ​Bosom Buddies i​ s purely functional.

https://www.youtube.com/watch?v=3UI_JwF3cnA
Bosom Buddies o ​ pening

In the same way that movies like ​Some Like It Hot​ is an adaptation of an earlier film
(France’s 1935 ​Fanfare of Love)​ , these early crossdressing films are in the vein of
Shakespeare’s works, and beyond that, a long tradition of crossdressing narratives that focus
less on identity and more on farce. But while they are not actively focused on identity, the
discursive power of the aesthetics of a man doing drag for comedy is actively harmful toward
real transgender individuals. It delegitimizes trans identities and paints genuine transition with
the air of farce.

Trans as pathology
As American film grew increasingly transgressive—both in violence and sexual
content—as the Hays Code fell out of use, narratives focusing on transgender individuals as
villains began to crop up. The most culturally significant instance of a trans villain is Norman
Bates in ​Psycho​ (1960). Here, Norman’s gender identity is the result of a twisted and abusive
relationship with his mother. He passes in between personalities, one as the meek Norman, the
other as his psychotically jealous mother. While in this state, Norman dresses in a wig and
women’s clothing.
While not an explicitly trans narrative, once again, this story creates an implicit link
between crossdressing and deviancy and violence. Norman’s impulse to kill is wrapped up with
his confused gender identity.

https://www.youtube.com/watch?v=xWHYmNrAFlI
Climax of ​Psycho​ (vaguely graphic)

This trope had strong staying power over the next 40 years, appearing regularly in
popular films as well as alternative horror. In ​Texas Chainsaw Massacre (​ 1974), Leatherface
alternatingly projects masculinity and femininity, wearing the face of a woman along with a wig
and a dress during a dinner scene. ​Sleepaway Camp (​ 1983), though not a popular or critical hit
(it’s mainly notorious for being incredibly bad) is one of the most aggressive films when it comes
to deviant transgender villains, with a psychotic antagonist who was forced to live as a woman
systematically murdering her fellow campmates.
These stories inextricably link transgender identity with the violent and absurd,
reinforcing a rhetoric of fear surrounding transgender individuals. Rather than marginalized
people, this was an identity that came about from intense trauma, and were to be treated with a
mix of fear, pity, and revulsion.

A time of contrasts
Before the 1990s, there are a surprising amount of somewhat empathetic narratives
about transgender individuals. Notable entries include ​Glen or Glenda​ (1935), an Ed Wood film
in which the director plays the title character, an examination of the auteur’s own struggle with
his gender identity; and ​Dog Day Afternoon​ (1975), which, although it is not entirely focused on
a trans narrative, is bound to its protagonist’s love for his partner, enough to rob a bank to pay
for a sex change operation for them.
While each of thse is not a masterpiece in transgender storytelling, they represent a shift
toward a more understanding creative process, one where trans narratives are neither strictly a
space for comedy or for fear. It’s in this space that the 1990s offer many conflicting entries. This
decade brought both strong strides in the quality of transgender representation, along with some
of the most mainstream instances of regressive uses of transgender identities for fear or
comedy.
Early entries like ​Orlando ​(1992) and ​The Crying Game​ (1992) show both an increase in
nuance and more legitimized forms of fear-based plots surrounding trans individuals. ​Orlando
focuses on an androgynous man who partway through the film spontaneously becomes a
woman. Narratively, it’s left ambiguous as to what Orlando’s assigned gender was and what
their identity is, but it’s a fairly sensitive and unfussy examination of a life lived with nonbinary
gender. ​The Crying Game​ is a political sex thriller, focused on multiple love affairs and a
character that reveals themselves to be transgender near the end of the film, taking the
revelation as a twist.
The ‘90s continued more or less in this vein, bouncing between wide releases with
widely varying narratives. 1993’s ​Mrs. Doubtfire ​has Robin Williams dressing up as a woman in
order to spend time with his kids, and certainly has a lot of fun with that concept. In 1994, ​Ace
Ventura f​ eatured a villain that is revealed to be transgender the whole time, both as a source of
fear and comedy. ​The Birdcage ​(1996, also has Robin Williams in it) uses the idea of a man in
drag for comedy, but also uses the inherent farce of the imagery to make some earnest and
empathetic points about queer lifestyles. ​Midnight in the Garden of Good and Evil​ (1997)
doesn’t make transgender issues the focus of the narrative, but is notable for having a trans
woman who was actually a part of the nonfiction book the film was based on, in the film.
The film that best represents the duality of increased attempts at empathetically telling
trans stories is 1999’s ​Boys Don’t Cry​ starring cisgender woman Hilary Swank as Brandon
Teena, a trans man who was raped and killed in Wyoming in 1993. The film drew wide acclaim
at the time, and Swank won an Academy Award for her performance. But while ​Boys Don’t Cry
takes a much more direct and authentic approach to a trans narrative than many films that
preceded it, it still falls into common pitfalls, leaving out important details about Brandon’s
gender identity and experiences, as well as reinforcing media narratives of the inevitability of
queer suffering.

https://www.youtube.com/watch?v=EAO9ZnpiCqw
Boys Don’t Cry,​ not a great clip but I’m doing my best over here

Race and drag

The 2000’s saw a shift from wide release films focusing on transgender individuals and
crossdressing to a strong presence in the independant filmmaking scene. Movies like ​Hedwig
and the Angry Inch (​ 2001), ​By Hook or By Crook​ (2001), and ​Tomboy​ (2011) continued an indie
filmmaking development that began in the 1990s with films like ​The Adventures of Priscilla,
Queen of the Desert ​(1994)​, I Shot Andy Warhol (​ 1996)​, ​and ​Better Than Chocolate ​(1999).
However, at the same time, films created by Black Americans were experiencing
unprecedented success. While far from universal, a somewhat common theme was deriving
comedy from a man dressed as a woman. Films like ​White Chicks​ (2004) and ​Juwanna Mann
(2002) revolve around men living secret lives as women for various reasons. Films like ​Norbit
(2007) and any ​Madea m ​ ovie involve comedians portraying women characters outright.

https://www.youtube.com/watch?v=LITIyNwO_HA
Juwanna Mann trailer

While debate over the acceptability of men doing drag for comedy has been broiling for a
while, the issue of Black men doing drag is magnitudes more complicated, roping in issues of
sexism, racism, emasculation, and transphobia. Some, like Todd Boyd, a professor at USC,
believe that Black men doing drag emasculates and weakens them, offering a pacified image of
Black masculinity. Boyd argues that emasculation of Black men is a racist trope extending back
into the days of slavery, and drag performances reinforce that imagery.
Many comedians who defend their decisions to perform in drag point to the happiness
the characters bring to audiences, and their own personal autonomy in creating the characters.
As quoted in a Los Angeles Times article, Chris Rock said “Men dressing as women is a
comedy staple, like a pie in the face. For a lot of film critics, the greatest comedy ever made is
Some Like It Hot,​ where Jack Lemmon and Tony Curtis dress up as women. I like Madea. I got
no problem with Madea.”
Some of these films, and others during the late ‘90s and ‘00s, continue the trend of
simultaneous progress and regression. Movies with a crossdressing protagonist like ​Juwanna
Mann​ show a man disguising himself as a woman, but experiencing misogyny himself and
realizing how his own negative treatment of women has affected others. It’s an idea that itself
isn’t entirely without value, that a man inhabiting the perspective of a woman realizes the depths
of misogyny, but to do so while dressed in drag mitigates much of the positive message these
films could have. It’s odd to point to a Mel Gibson film as being any kind of progressive success,
but ​What Women Want​ (2000), as much of a mess as it is, deals with this concept much more
cleanly.

Trans as prestige
Over the last decade, drag used as comedy and real trans narratives diverged even
farther. No major film was released featuring a trans character as the object of comedy, and
films featuring men in drag as a major plot point decreased, for the most part, aside from
notable exceptions like the continually successful ​Madea f​ ranchise. The 2010s were also a
decade of increased national awareness of transgender issues, both positive and negative.
Increased pushes for positive representation and transgender rights made transgender stories
more visible than they had been before, while an inverse negative reaction saw pushes for
legislation limiting transgender individuals’ rights.
The increased discussion over trans representation in film also led to a breaking point
with trans narratives. During the first half of the decade, multiple movies were released featuring
cisgender actors portraying trans characters, and receiving considerable amounts of acclaim for
it. In many ways, the trans story had gone mainstream, and was seen as a considerable acting
challenge.
In those five years, Glenn Close was nominated for an Oscar for playing a trans man in
Albert Nobbs (​ 2011), Jared Leto won an Oscar for playing a trans woman in ​Dallas Buyers Club
(2013), and Eddie Redmayne was nominated for playing a trans woman in ​The Danish Girl
(2015). None of these films were written or directed by trans filmmakers, and none of the
characters were depicted by trans actors.

https://www.youtube.com/watch?v=d88APYIGkjk
The Danish Girl, trailer (warning: eddie redmayne)

In the back half of the decade, however, negative reception of these stories increased.
While they were telling trans stories with a greater degree of empathy than many films that
preceded them, they were also directly profiting off of transgender experiences while not
including any (or few) trans cast or crew in the process. Criticism of casting cisgender actors as
trans characters increased.
Though films featuring trans narratives didn’t disappear during these years, the
increased scrutiny proved to outweigh the perceived prestige that could be gained from these
movies, and a number of them were canceled, delayed, or recast, most notably in 2018 with
Scarlett Johansson withdrawing from a role as a trans man in ​Rub & Tug, ​leading to the film
closing production.

———————————

The history of creating films with trans narratives is one littered with misogyny,
transphobia, and racism, as well as failed earnest efforts, incremental progress, and mainstream
recognition. Slowly, over time, we see a picture of increased empathy and attempts to
understand trans perspectives, however misguided. More recently, ​Tangerine ​(2015) or ​A
Fantastic Woman​ (2017) are examples of movies featuring transgender actors in transgender
roles, telling transgender stories, and receiving recognition and acclaim. While mainstream films
might not have space for the complex empathy required to deliver these narratives in a fair way,
the path toward greater autonomy of trans individuals to tell their stories is becoming more
clear.