Cowboy Cross-dressers – Sex in the Wild West

Calamity Jane, Little Joe Monahan, and Mrs. Nash… What was life like for those who dared to cross-dress in the Wild West? Why were their stories twisted to fit an emerging American mythos in the 20th century? And what does that say about how we view cross-dressing today?

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[Ballad of Little Jo trailer clips]

The West was no place for a woman. And so, what’s a girl to do, but become a man?

Or at least, that’s what we are led to believe by Westerns like the 1993 film The Ballad of Little Jo, from whose trailer we just heard clips. The film tells the story of Little Joe Monahan, born Johanna Monahan, a real-life cowboy who dressed, worked, and lived as a man.

Why? Well, according to the movie trailer, to survive. “Throughout history, society has driven women to make difficult decisions in the name of survival” – that’s what it says.

But a look at the life of the real Little Joe reveals Joe was pretty much accepted by locals, and no one was even very surprised when Joe’s secret was discovered upon death. They always kinda suspected it.

So, that’s odd. The movie makes it seem like the West was such a rough place, such a man’s world, that a women might have to become a man just to get by.

But as we learned in our last episode in this this series, the West was actually a surprisingly progressive place for women. Yes, it was rough, and yes, it could be violent, including violence against women. At the same time, however, the scarcity of women gave them power, because their skills were in demand. Women could actually do quite well in the West because they were women, not in spite of it.

Nor is Little Joe the only person who’s received this treatment in Westerns. The same happened to Charley Parkhurst, Sammy Williams, and many other historical figures who cross-dressed in the West. Films, books, and news articles going all the way back to the turn of the century, just after the closing of the frontier, have altered the stories of dozens of real-life frontier folk to depict cross-dressing as necessary to survive, despite evidence to the contrary.

Why would they do that?

It gets stranger still.

See, it wasn’t just women who cross-dressed as men in the West, but also men who cross-dressed as women. Historian Peter Boag presents nearly as many cases of male-to-female cross-dressing as female-to-male in the historical record, yet this is almost entirely absent from Westerns. Women cross-dressing as men get portrayed as needing to do so for survival, while men cross-dressing as women barely get portrayed at all.


And then we come to the most famous frontier cross-dresser of all, Calamity Jane, who in almost every portrayal is depicted as dressing in men’s clothes on a daily basis and looking awkward as a fish out of water when made to put on a dress. Yet a look at the real life Calamity Jane reveals she didn’t actually cross-dress all that often, seems to have identified quite comfortably as female, wore a skirt and bustle more often than not, and by all accounts cut a swell doing it.

(cut a swell: to present a fine figure)

That’s authentic frontier lingo for you there.

Calamity Jane seems to have been far more normal than we’ve been led to believe. Why would Westerns depict her as more transgressive than she was, while others get depicted as less so or not depicted at all?

What’s going on here? What is being erased in this most American of genres, the Western? And what does it say about our sense of Americanness today?

That’s what we’re talking about in today’s episode. I’m B. T. Newberg, and this is The History of Sex.


I’d like to thank our Patreon patron Nora for making this episode possible.

Folks, when this show started a little over two years ago, our very first teaser episode began by invoking anxieties some feel about the emphasis on diversity in sex and gender today:

[clip: “It makes you long for a time when men were men and women and were women, and nothing could be more clear, right?”]

Ever since, every episode has proven that there never was such a time. From hunter-gatherers, to ancient Sumer, to Greece and Rome, to the Vikings, to Victorian England, it was never that simple. Sex and gender norms are not written in stone, they change, and they’re always fuzzy, always complicated. The diversity today just feels new because our culture is finally waking up to that fact.

But it’s easy to say well sure, that was Greece, or that was Rome. It’s much harder when it’s your own culture. And for Americans, it’s especially hard – not only because we are internationally renowned for thinking we are the exception to every rule, but also because we have built up an entire mythos for ourselves about how the frontier made us tough, made us “real men”, not like those effeminate Europeans with their fancy cities and decadent luxuries.

That idea may sound today like stretching the blanket.

(stretching the blanket: telling a tall tale)

Maybe it is stretching the blanket to say the frontier makes us special, but the idea was taken seriously in the late 19th and much of the 20th century, and it was propagated through news, books, and movies.

Now, I’m not saying this is some kind of consciously-planned effort to remake America, like some kind of Illuminati conspiracy. For the most part it was probably unconscious assumptions biasing editors, authors, and filmmakers.

But it could at times be quite deliberate. For example, Teddy Roosevelt deliberately re-engineered his public image along these very lines. As historian Peter Boag writes:

“Smarting from snide remarks about his effete fashion sense, and mindful of his squeaky voice and asthmatic and underdeveloped body, in the 1880s Roosevelt purchased two ranches in the Dakota badlands and spent considerable time there making over his physique, his tenor, his health, his clothing, and his image. … He then published extensively about his western experiences, lavishing details on how the frontier transformed him into a manly hero akin to the cowboy” (p. 152).

So that was quite deliberate. It’s no joke. This was a real shift in American culture. As Peter Boag explains:

“Myths of the West and of the frontier worked hand-in-hand with period anxieties about cross-dressing and about strong and independent women to produce… a heterosexualized and gender normalized version of the birth of the modern American nation” (Boag, p. 104-105).

Roosevelt was responding to that new version of America’s birth, which was already in the air in his time. And he contributed to it by reshaping himself in a very public way. This idea then made its way into scholarship in 1893 when historian Frederick Jackson Turner put forward his “frontier thesis” that America was born in and indelibly shaped by the wilderness of the frontier. And from there, it’s history.

Ever since, American news, books, and films, especially those of the Western genre, have been reshaping American manliness to fit this image, consciously or not. From Louis L’Amour to John Wayne to Clint Eastwood, the rough-riding cowboy now lies at the heart of American masculinity. Or at least White masculinity; we’ll have a look at how minorities got excluded from this later in this episode. But for the majority culture, as the story goes, it was the frontier wilderness itself that toughened a man up into a regular curly wolf.

(curly wolf: a real tough guy, a dangerous man)

Okay, so what does this have to do with cross-dressers in the West? Well, to reshape America as born on the frontier, the tale of the frontier had to be told, but certain very visible elements of it had to massaged to fit the story. If you’ve got this idea that men were men and women were women, and the frontier made it so, then what do you do with women who dressed as men, or men who dressed as women? How do you take those stories and make them support this American mythos?

Well, it seems that American editors, authors, and filmmakers found a way.

Cross-dressing on the Frontier

Cross-dressing happened a fair amount in the Wild West. And when I say that, I’m mainly talking about settlers. If you include the native inhabitants of the frontier lands, it was especially common, even downright institutionalized, depending on the tribe. Many Native American tribes had third gender traditions, such as the winkte of the Lakota and Dakota, nádleeh of the Navajo, hwame of the Mohave, and many more. These third gender traditions often included dressing in the clothing opposite the sex assigned at birth. We will touch lightly on these traditions today, but each of them have such distinct cultural contexts that they deserve an episode in their own right, so we will wait for our episode on Native Americans in the West to go into depth. Nevertheless, I want to acknowledge at the outset that there is a larger context here.

Among settlers on the frontier, cross-dressing was not institutionalized, but it was surprisingly frequent. I say surprising not because it happened any more frequently there than elsewhere, but rather because the West has been made out to be this place of manly-manliness. But no, it happened just as often as in any other place. Historian Peter Boag, in his book Re-dressing America’s Frontier Past, presents close to 100 historically-verified examples, in about roughly equal numbers for female-to-male and male-to-female cross-dressers.

This was not infrequent. And yet, portrayals in news, books, and films have spun the image of the West as a place where such people shouldn’t have existed, and if they did, there must be some explanation.

And that is how we arrive at the Western genre where women dressing as men appear in abundance but do in order to survive, whereas men dressing as women almost never appear at all, or only in very special circumstances.

See, if the frontier wilderness toughens you up and demands you become a “real man” in order to survive, then maybe it demands women do the same. The narrative of women dressing as men in order to survive fits hand-in-glove with the mythos of American masculinity.

Boag calls this the “progress narrative”, part of the American mythos that eased 20th-century anxieties about cross-dressing and non-normative sexual and gender expression. As “progress” came to the West, the frontier closed, and its dangers were tamed, the need to cross-dress in order to survive evaporated with it, leaving it comfortably in the past, a blip in history. Nevermind that it still went on as much as it ever did; the important part was that a troubling phenomenon right at the focal point of American history had been explained.

On the other hand, what was not so easy to explain by the progress narrative was men dressing as women. It just didn’t make any sense: if the wilderness demanded you become a “real man” to survive, even if you were a woman, then why would any man become a woman? It undermined the narrative, and so such folks had to be excised from the story. That’s why in Western cinema you see gals in chaps all the time, but you almost never see chaps in bustles. It’s all about this American mythos that we were made tough and manly by the frontier.

This, in turn, is but the American version of a much larger pattern seen across cultures. For example, we saw in our Viking gender benders series how women who took up arms like men could earn respect, while men who took up the womanly art of sorcery were reviled. See, in a patriarchal culture, the male sphere has higher status, so women attempting to enter that sphere can be explained as an attempt to gain higher status. However, men who debase themselves by entering the lower-status female sphere is far more troubling.

And that’s still with us today. When you see Sharon Stone as a gunslinger in pants in The Quick and the Dead, it probably doesn’t even stand out to you as cross-dressing, even though it would have been. That’s how far we’ve come. But if you saw Clint Eastwood in a dress, it would definitely stand out to you. That’s how far we have yet to go.

This is the larger pattern we’re seeing here in the Wild West as well, just tailored to serve a particular purpose in American myth-making.

So, how did this happen, and what was the West really like for cross-dressers? We’re going to find out, but first we should back up and get a quick primer on what cross-dressing is.

Defining Cross-dressing

Okay, so let’s begin with our quick primer. As we heard in our earlier episode “Wolves in Women’s Clothing” from our Sex in the Third Reich series, cross-dressing refers to wearing clothing associated with a sex different from your own or from that assigned at birth. It used to be called transvestitism, but that term is now considered outdated and possibly derogatory. The preferred term today is cross-dressing.

This is typically thought of in binary terms, divided into female-to-male, where an assigned-female person wears the clothes of a male, and male-to-female, where the opposite is the case. However, the binary breaks down when you consider nonbinary folks, or intersex folks, or dress that is androgenous, or dress that mixes clothing from both sexes. I mean, is that technically cross-dressing? It gets fuzzy. The best takes I’ve seen recently online are “cross-dressing is when you dress outside your gender category,” or even just “It’s cross-dressing when I want it to be.” So, essentially, we just have to acknowledge that the categories here are blurry at best and evolving along with the preferences of the community.

Now, within that community, there are folks who attempt to appear so much like another gender that others would never suspect, and this is called “passing.” Others make no such attempt, leaving it clearly obvious that cross-dressing is happening.

It’s important to note that none of this necessarily implies anything about sexuality or gender. It may go along with homosexual or bisexual desire, but need not; heterosexuals may cross-dress as well. Likewise, it may go hand-in-hand with a transgender identity, as seems to possibly have been the case with Little Joe Monahan. Indeed, cross-dressing is often an expression of transgender identity. On the other hand, cross-dressers may be entirely comfortable with their assigned sex, as seems to have been the case with Calamity Jane. So, in short, cross-dressing, sexuality, and gender are three separate concepts. In the Venn diagram in our minds, we have to picture three different circles that overlap partially but not entirely.

Finally, we should also talk about pronouns. Today, a person’s preferred pronouns are theirs to decide, but when it comes to historical figures, they didn’t have that choice in their day and we can’t go back and ask them what they’d have preferred if they did. So, the best we can do is make a judgment call. I’ll generally attempt to use the pronouns that seem to match how they tended to present themselves to the world, but it’s really anyone’s call.

Alright, with that quick primer, let’s talk about how cross-dressing in the Wild West has been portrayed by editors, authors, and filmmakers.

Consciously or unconsciously, they adopted different strategies depending on who they were writing about. We’ll look at three specific cases: first, women who cross-dressed as men, such as Little Joe Monahan, then men who cross-dressed as women, and finally Calamity Jane, who didn’t actually cross-dress that much but has been made to do so in the Western genre ever since. Through these cases, we’ll see how cross-dressing was transformed to support the notion that American manliness was forged on the frontier.

That’s what we’re going to look at in just a moment. But first, we’ll take a short break, and we’ll be back after this.


Alright, we’re back.

So, what was it like for women who cross-dressed as men?

Women Who Dressed As Men

Little Joe Monahan wasn’t the only woman who dressed as a man in the West. There were many, and they did so for a variety of reasons. Some did so for reasons of personal safety. Boag presents 3 cases where women traveling alone put on male attire to avoid unwanted attention, and there were likely more. But this was by no means the only reason. Others cross-dressed to join the military, to obtain work in jobs exclusive to men, or for some kind of criminal activity. These are all practical reasons that don’t necessarily reflect anything about one’s predilections or deep-down feelings.

But then there were those who appear to have cross-dressed for a very different reason: personal identity. These are people like Little Joe, who seem to have cross-dressed as an expression of a gender at odds with that assigned at birth, a sexuality alternative to the norm, or a predilection for putting on opposite-sex clothing not explained by more practical reasons. Boag presents no less than 15 such individuals. It’s these folks who present a problem for the American mythos. Their stories were frequently edited and transformed beyond recognition in news, books, and movies.

For example, here’s what happened to the story of Little Joe.

The real Little Joe Monahan lived a quiet, solitary, and fairly unremarkable life as a cowboy-turned-miner-turned-rancher in the Owyhee (O-WYE-hee) Mountains of Idaho. He moved there from New York at around the age of 20, and was apparently accepted by locals there, despite not passing particularly well as a male. An 1880 census records his sex as male but notes “Doubtful Sex” (Boag, p. 101). Nevertheless, Joe was respected by locals, and lived the rest of his days as a man until his death in 1904, whereupon the coroner identified his body as that of a woman.

At that point, a local acquaintance by the name of William Schnabel took it upon himself to notify Joe’s kin back east of his passing. To that end, he wrote a letter to the police of Buffalo, New York, and the police turned the letter over to the papers to advertise for those who might know his relatives.

However, from the moment the papers got hold of Schnabel’s letter, Joe’s story began to mutate. An article in the American Journal Examiner is a case in point. Although Schnabel referred to him as “he” and “him”, the Examiner editors changed this to “she” and “her.” Further, although Schnabel spelled Joe’s name in the masculine form J-O-E, editors changed this to the feminine form J-O. Finally, to explain his cross-dressing, they added this fine detail:

“In those days a journey across the continent was an undertaking attended by many hardships and not a few dangers. This was the more so in the case of a woman traveling alone. It was on this account that the brave little woman decided to don the more conventional attire of the male sex, discarding her own dress with her past” (Quoted in Boag, p. 103).

Now, historians know this was not the reason Joe started cross-dressing. It was not in Schnabel’s letter, it doesn’t explain why Joe would continue cross-dressing after arriving in Idaho, and a separate letter from his foster mother reveals Joe had actually been dressing in boy’s clothes since childhood (Boag, p. 99). So, editors made the conscious decision to insert this detail into Joe’s story.

But not content to stop there, they also concocted out of thin air a love affair:

“This is the closing chapter in the life story of a beautiful girl who loved not wisely but too well a villain by whom she was deserted in her darkest hour, who was driven from her home into a pitiless world…” (quoted in Boag, p. 102-103).

Where did that come from? Suddenly there’s a relationship with a man that goes all catawampus?

(catawampus: askew, awry)

This was certainly not in Schnabel’s letter, and historians have no evidence of a relationship of any kind. But the editorial insertion of this love affair served a purpose. Not only did it spice up the story with a little drama, but it clarified that in spite of the cross-dressing, Joe was in fact unambiguously heterosexual.

Now, this was a new concern. Earlier reports of cross-dressers typically remarked on the oddity of it and attributed a “rational” reason like survival, but starting around the turn of the century, just after the closing of the frontier, cross-dressing became increasingly caught up with sexuality.

See, the concept of heterosexuality had been established in academic circles by this time and was gaining traction in the wider culture, as was the concept of “sexual inversion” – a sort of catch-all category for alternative sexuality and gender. So, the editors of this article published in 1904 took it upon themselves to fend off the possibility of sexual inversion by placing Joe comfortably in the unthreatening category of heterosexual.

So, in total, these newspaper editors made Joe into an unambiguously straight, cisgender female, victimized by a man in a man’s world, and explained away the cross-dressing as necessary for survival in a Wild West dominated by men.

And in so doing, intentionally or not, they removed any threat to the new American mythos. The frontier does indeed breed “real men”, so much so that even women might have to become men in order to survive.

At the same time, they completely erased the real Little Joe, whose cross-dressing began back east and had nothing to do with surviving the West.

In fact, Joe was respected in the West. Schnabel writes in his letter that cowboys of the area “treated him with the greatest respect, and he was always welcome to eat and sleep at their camp” (quoted in Boag, p. 101). This was in spite of the fact that his secret was not particularly well-hid. Schnabel writes: “it was always surmised that Joe was a woman…. He was a small, beardless, little man with the hands, feet, stature and voice of a woman” (p. 100). So, local always kinda knew, and they accepted him anyway.

This was not always the case for cross-dressers in the West. Some were accepted, but many others were rejected, even violently. So, it’s true that if you were a cross-dresser, you might want to keep that dry.

(keep that dry: to keep a secret)

Often it was those enmeshed in their local communities who were more likely to be accepted, while those who were outsiders or drifters risked violent reprisal.

Joe was one of the lucky ones in life, accepted and respected. Nevertheless, the papers transformed this into a desperate need to dress as a man in order to survive the West, and Joe’s story only grew from there. After a flurry of sensational newspaper reports in the early 20th century, Joe’s story resurfaced in the 1950s in books and newspaper columns, and was even made into a stage play by dramatist Barbara Lebow. Finally, in 1993, Hollywood picked up the tale with The Ballad of Little Jo, from which we heard clips at the start of this episode. All of these kept to the same mold of an unambiguously cisgender and heterosexual woman putting on men’s clothes in order to survive.

Many other examples followed the same pattern.

For example, Charley Parkhurst, better known as Stagecoach Charley, lived as a man in California since the 1850s and was only discovered upon death. Yet, newspapers mutated his story along very similar lines, making him an unambiguously cisgender, heterosexual woman with a love affair with a male that went awry. Even his name was likewise changed: Charley became “Charlotte” or “Lotte” in the papers (Boag, p. 106-107).

Likewise was Sammy Williams, a Montana resident who lived for some fifty years as a man. After his secret was discovered upon death, Boise’s Idaho Statesman ran an editorial about it arguing that women might gain enhanced prerogatives, freedoms, and earning power by dressing as men, and called it “a marvel that more women have not adopted the course of ‘Sammy’ Williams” (quoted in Boag, p. 32). In other words, the article supposes Sammy’s motive was economic survival.

You even see this pattern show up in fiction. For example, in the 1971 film Hannie Caulder, Racquel Welch stars as a woman assaulted by men who puts on pants and quests for vengeance, while in the 1995 film The Quick and the Dead, Sharon Stone stars as a gunslinger also on a quest for vengeance against a man who’d done her father wrong, and she does her gunslinging in men’s attire, as if a pistol could not be fired in a dress (Annie Oakley would protest!). In both productions, a male relationship goes awry and a woman takes up cross-dressing in order to survive, while remaining unambiguously straight and female.

So, that is how the stories of women who dressed as men were transformed to fit the American mythos. But what about men who dressed as women?

Men Who Dressed As Women

The Western genre is so full of female-to-male cross-dressing that is has become something of a stock character. What it is not full of is male-to-female cross-dressing. This happened in no small numbers as well in the Wild West. Peter Boag presents more than 50 historically-verifiable instances.

Now, we have far less information on the lives of these individuals than we do for female-to-male cases. Typically, we only know of male-to-female cross dressers through arrest records, and such prisoners tended to be tight-lipped about their motives. However, from what we can tell, their reasons too were quite varied.

Of the 50+ cases, only half reveal any kind of identifiable motive. Of those 25 or so, about half were motivated by practicality, whether as a disguise for criminal activity, a practical joke, or theatrical performance (it was quite common for men to play women on stage at the time). One case cites personal comfort as the reason for donning women’s dress: Henry Snell claimed men’s vests and trousers were too restrictive for his rheumatism, so preferred dresses.

The other half appears to be matters of personal identity. So, male-to-female cross-dressing for personal gender or sexual expression was not rare either. There are plenty of historically-verifiable examples. Boag is able to assemble about as many as for female-to-male.

And yet, male-to-female cross-dressing is almost entirely absent from the Western genre, and in the paltry handful of instances I could find, almost all of them were motivated by disguise to evade pursuers or perform some criminal activity. I could only find two instances in the entire genre where this was not the case.

The first is the very recent 2020 series Good Lord Bird, depicting the lead up to the Civil War, where a young Black boy nicknamed “Onion” is mistaken for a girl by the White abolitionist John Brown and made to wear a dress while traveling with him. This cross-dressing seems symbolic of the experience of Blacks forced to conform to the perceptions of Whites, even those purporting to help them. It’s not a disguise per se, but it’s not personal identity either.

The only instance I could find in the entire Western genre where male-to-female cross-dressing might be motivated by personal identity is a character played by none other than Iggy Pop in a scene from Jim Jarsmuch’s 1995 film Dead Man. In that scene, Johnny Depp’s character stumbles upon three men in the woods, one of which wears a dress and sunbonnet, apparently the wife of the other two. The scene is clearly there for comedic effect, yet it holds the honor of being the only instance I could find where male-to-female cross-dressing goes unquestioned and unexplained and might very well portray a matter of personal identity.

So, that is all I could find for male-to-female cross-dressing in Westerns. It’s been almost completely excised from the genre, even though female-to-male cross-dressing appears in abundance.

Why? Well, if the underlying notion of the Western genre is that the wilderness turns you into tough “real men”, then the presence of men dressing as women in that same wilderness doesn’t exactly fit that notion, does it? Consequently, it’s conveniently forgotten in books and films.

For newspapers, it was not so easy to omit. After all, a man in a woman’s dress does make for an attention-getting headline, so editors could not so easily excise them from the written word. They had to find a different way to square it with the American mythos, and they did so by going out of their way to call these individuals out as foreign or racially other.

For example, Mrs. Nash, who famously accompanied Custer’s 7th Cavalry division as a laundress and was written about in Libbie Custer’s journal, is noted repeatedly as having Mexican heritage, and was even called simply “The Mexican” by most in the division. Meanwhile, newspapers reported on Edward Martino as a “Spaniard”, Chin Ling as a “Chinaman”, Bill Smith as an “African”, a certain Frank (last name unknown) as a “Negro”, Edward Livenash as a “negro wench”, and a person who was called Lady Jim or Squaw Charley is remarked upon as a Paiute Indian. The press even concocted a story of his tribe punishing him with women’s clothing after disgracing himself in the Pyramid Lake War of 1869. This is unlikely, but may reflect a dim awareness of customs among certain Native American tribes involving third genders who wore clothing of the opposite sex to mark their different and sometimes sacred status.

We will leave such Native customs for another episode where we can do them proper justice. For now, it is sufficient to note that settlers had a poor understanding of them, and scholarship on it at the time was not very good either. Newspapers may have drawn on this dim awareness of Native American third genders to cast male-to-female cross-dressers like Lady Jim as other.

In addition, the Mexican-American War was still smoldering in recent memory, and wartime effeminization of Mexican soldiers may have likewise contributed to the readiness of newspapers to emphasize the foreignness of Spanish-speaking cross-dressers like Mrs. Nash and Edward Martino (Boag, p. 145).

Meanwhile, long-standing racial stereotypes of Blacks as docile and therefore of questionable masculinity lent a ready explanation for cross-dressing in cases where any hint of African origin might be noted, and the traditional hairstyles of Chinese men, with their long braids, appeared feminine to Whites, and likewise provided a rationale ready-to-hand (Boag, p. 147).

As a result, American manliness was saved. Although these folks were often in fact Americans as much as anyone else, emphasizing their racial or ethnic status cast them as aliens to their own kind. Where male-to-female cross-dressing could not be removed from the American mythos, it was cast outside it.

So, in the end, the experiences of cross-dressers in the Wild West, and their real motives for their choice of attire, were obscured by newspapers, books, and films. We’ve seen how female-to-male cross-dressers were made to appear straight cisgender women who could not help but dress as men to survive the frontier. And we’ve seen how male-to-female cross-dressers were either conveniently forgotten or made into not-quite-Americans.

Last but not least, we have one last case to investigate: that of the most famous Wild West cross-dresser of all, Calamity Jane.

Calamity Jane

In the light of everything said so far, Calamity Jane would seem to present a startling exception. Her story actually mutated in the other direction, being made more transgressive than she really was in real life. But a closer inspection reveals how this too supports the American mythos.

There is very little we can know for certain about Calamity Jane’s life, as so much of the lore about her is grossly exaggerated, up to and including her very own autobiography. In her autobiography, she claims to have begun wearing men’s clothes to join Custer’s army, but no historical evidence supports she was ever even in the army. Her autobiography was published to publicize an upcoming tour, and it seems she was not above stringing a whizzer

(stringing a whizzer: telling a tall tale)

to add a little oomph to her tour. Thus, the real reason for her cross-dressing, as with so much about her, remains in dispute.

However, from what we can verify of the real Calamity Jane, it seems Martha Jane Cannery only rarely cross-dressed. There is a famous photo of her in buckskins, and she did sometimes wear them as daily dress, but the vast majority of photos show her in a dress. This seems to have been how she presented to the world most often, that is as a cisgender female. Moreover, she seems to have been straight as well. She married, bore a daughter, and may have resorted to prostitution at various points in her career. She did engage in many male-coded activities, including cigar smoking and hanging out in saloons. She was apparently quite fond of the Who-hit-John.

(who-hit-John: liquor, beer, spirits)

But apart from these acts of gender defiance, she seems to have been within the norm for her day.

Yet, portrayals of Calamity Jane tend to exaggerate her gender defiance and make it into a greater deviation than it was. For example, in the 1878 dime novel Deadwood Dick on Deck: Or Calamity Jane, the Heroine of Whoop-up, other characters ask if she is a woman, and she replies: “Well, yes, I reckon I am in the flesh, but not in spirit o’ late years. Ye see, they kind o’ got matters discomfuddled w’en I was created, an’ I turned out to be a gal instead of a man, which I ought to hev been” (quoted in Boag, p. 108).

This seems to suggest a deep-down trait potentially inherent to Jane’s identity. “I ought to hev been [a man]” almost sounds like something a transgender person might say, though this was written more than 40 years before the concept of transgender identity was first proposed in the 1920s. So, the novel seems to make her more transgressive than she was in real life, bringing her more in line with the trope of figures like Little Joe, Charley Parkhurst, and Sammy Williams.

Later portrayals follow similar lines. For example, the 1953 film Calamity Jane stars Doris Day as a Jane who dresses daily in men’s attire, and appears like a fish out of water when she is made to actually wear a dress.

Yet such portrayals rarely fail to leave her unambiguously straight and cisgender in the end. A later dime novel sees her marry, as does the Doris Day film where she ties the knot with Wild Bill Hickock (which never happened).

They also tend to rationalize her cross-dressing as survival. Deadwood Dick on Deck explains it as due to “a man’s defiling touch”, a “villain… who foully robbed Jane Forrest of her maiden name, but never her honor” (Boag, p. 108).

In other words, Jane’s story evolved to fit the same pattern as the others. And although it went the opposite direction as most, it still supports the same fundamental notion of a man’s world where only “real men” can survive. In such a world, it simply won’t do to have Jane in a dress most of the time. No, it must be buckskins, buckskins, buckskins. And so it went with the tale of Calamity Jane. Her story was made just transgressive enough to be titillating but not enough to threaten the cisgender and heterosexual norms of the day.

That seems to be true all the way almost up to the present, but there is an interesting twist on the horizon.

The portrayal of Calamity Jane with which listeners are no doubt most familiar is Robin Sweigert’s irascible, foul-mouthed Jane from the HBO series Deadwood.


Just as with the others, she is made to wear buckskins all day every day, and appears a fish out of water when she does put on a dress. In this respect, she follows the established pattern to a T.

However, in this rendition, (spoiler alert) she engages in an affair with another woman. Deadwood differs from the others by making her non-heterosexual, even though the real-life Jane was straight as far as we can tell.

Likewise in the recent Netflix series Godless, played by Meritt Weaver plays Mary Agnes McNue, a widow who begins wearing men’s clothes after her husband is killed in a mining accident. This is a fictional character with no historical antecedent, but interestingly she too takes up an affair with another woman.

So, what are we to make of this? Is the Western trope of the female-to-male cross-dresser changing to explain it as the result of alternative sexuality? And if so, does that somehow emanate from a changing view of Americanness itself?

It’s probably too early to tell. Two data points are not much of a pattern, I admit. But it is certainly curious that as values change and greater diversity arrives in the Western genre, it doesn’t necessarily mean historical figures get portrayed more accurately. It only means we transform history to suit the needs of the day and the myth we tell ourselves about what it means to be American.

In this case, does it mean that we’re trying to say that America is and always was accepting and tolerant of these sorts of things? I can’t say that’s historically accurate either, but it may be what we would like to tell ourselves.

So, we’ll leave it there. But in closing, I’ll just say that personally, when it comes to historical figures, I prefer we simply acknowledge the corn.

(acknowledge the corn: to admit the truth)


Well, that’s all I’ve got for you today, folks. If you like what we’re doing here on this show, be sure to subscribe, rate, and review on Apple Podcasts or wherever you get your podcasts. Or you can pledge on Patreon where $5 a month gets you a portrait in the culture and time period of your choosing. I will draw you havin’ a hootin’ and hollerin’ good time in the Wild West wearing whatever you darn well please. Or whatever you want. I’ll make you look awesome, I promise. Just go to That’s

Alright, folks, next up I’m hoping to dive into the African American experience in the West. Did you know that as many as 1 in 4 cowboys in the West were Black? It’s true, and there were entirely Black towns as well. So, what was that like for them? That’s what’s coming up next.

I’ll see you then. I’m B. T. Newberg, and this is The History of Sex.


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Wright, Robert. The Evolution of God. New York: Little, Brown, and Co., 2009.

Sources for Authentic Frontier Lingo

Western Slang & Phrases: A Writer’s Guide to the Old West

Cowboy Bob’s Dictionary

Cowboy Lingo Dictionary

Audio Credits

Podcast theme music mixed from “Gregorian Chant”, “Mystery Sax”, and “There It Is” by Kevin MacLeod.

Episode theme music “Rattlesnake Railroad” by Brett Van Donsel from Music for Content Creators.

“American History Whack-a-Mole” skit mixed from “Fairground Sound Effect” from Played N Faved, “Whack a Mole Night Market” from Anas Kali, “Hammering Hitting Wood Sound Effect” from Fesliyan Studios, “Waterphone Bottom Hits Rubber Mallet” from siccSoundFX.

Other audio from:

The Ballad of Little Jo Trailer 1993” from Video Detective

Calamity Jane Deadwood Moments” from TheDeadwoodFan

All narration and voice acting by B. T. Newberg

Image Credits

Victorian lady silhouette from and Top Hat & Mustache from Clipart Library


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