John Herbert had a gift for the written word.
As an 18-year-old in the 1940s, he put that talent to work in the advertising department at Eaton’s What his coworkers at the department store didn’t know was that Herbert liked to wear women’s clothing and perform in drag shows.
While it hurt no one and brought him joy, his after-work activities were generally unacceptable in society.
And at the time, it came with risk because in Canada, a man wearing women’s clothing in public was illegal.
Every time Herbert went out dressed as a woman, he was skirting the law.
Aside from that he endured taunts, threats and even assaults from others.
In 1947, a group of young men tried to rob him.
Police intervened quickly to arrest the perpetrators.
But the thieves falsely claimed Herbert had solicited them for sex.
As soon as police saw that Herbert was a man dressed as a woman, he became the villain.
He was arrested and charged.
Herbert, the victim of a robbery, was sentenced to four months in prison.
His attackers received no punishment.
But in the end John Herbert had the last laugh.
Because he took the pain of that incident and turned it into literary gold.
I’m Craig Baird, this is Canadian History Ehx and today we are looking at Canada’s drag history!
Before we begin… what is drag?
RuPaul Charles – the world-famous drag queen and creator of the award-winning show RuPaul’s Drag Race always says, “We’re all born naked, and the rest is drag.”
While in conversation with Oprah Winfrey, he expanded on it with her to dig deeper into what that means and at its core people are born as spiritual beings and the rest is all an illusion.
We come up with the definitions about who we really are.
As an art form, drag is about freedom of expression in its truest form.
It is a social commentary that challenges norms and stereotypes while infusing joy and humour into it.
It is also a community.
So much more than just sparkles, wigs and a song and dance.
Here’s Miss Moco, one of Canada’s leading drag queens.
Thanks to shows like Drag Race it seems like drag is a new thing.
And if you think about it, that reality competition show debuted in the United States on February 2, 2009.
That’s sixteen years ago, and even then, drag far predates television.
In fact, there’s evidence of drag long before Canada even existed.
Among Indigenous People, gender fluidity and cross-dressing was not viewed in a negative manner as it came to be among settlers.
Often termed Two-Spirit, these individuals were said to embody both male and female spirits.
Some Two-Spirit individuals adopted gender roles often associated with the opposite sex or wore the clothing of the opposite sex.
In many societies, they were revered as leaders, healers and visionaries.
Believed to be blessed with the ability to move between genders.
Even among Europeans, drag and cross-dressing had a long history.
It was even accepted but only in certain circumstances.
When Samuel de Champlain founded Quebec City and New France in the early-1600s, men were often in drag as they performed Shakespeare’s plays on the other side of the Atlantic.
As the vessels Erebus and Terror sat encased in ice in the Canadian Arctic in the early 1840s, Sir John Franklin and his all-male crew put on pantomime performances dressed as women to break the monotony of winter.
Even during war time, drag was a way to boost morale, and forget the horrors of the battlefield.
While the First World War raged in France, a drag group known as The Dumbells performed near the frontlines.
Made up of soldiers from the Third Canadian Division, the men played a variety of skits as female impersonators with such characters as Marie from Montreal.
They also did renditions of the latest popular songs as well as original material. le
The group’s name came from the divisional patch they wore, which had a red dumbbell on a blue/grey field.
The Dumbells became incredibly popular, often putting on three to four shows a day and the best-known female impersonator was often credited as Ross “Marjorie” Hamilton.
Often shellfire interrupted shows and on occasion the actors were commandeered to carry wounded soldiers on stretchers to first aid stations.
The World-famous troupe was created by Merton Plunkett who was originally from Orillia, Ontario.
By the summer of 1918 Merton had organized and outfitted different troops all paid for by the Canadian YMCA.
A year later they were on their first national tour.
After the war, the group remained together well into the 1930s and released 27 recordings and sheet music of their songs.
When Lucy Maud Montgomery saw their performance in Toronto in November 1921, she wrote in her diary,
“It was incredibly funny, and I laughed as I haven’t laughed in years. The female parts were all played by men and three of them were the most stunning beauties I ever beheld.”
As their popularity grew, they went on to play shows in London’s West End and at The Ambassador Theater on Broadway
With financial difficulties looming during The Great Depression, and the growth of the film industry, The Dumbells disbanded in 1932.
And while men in drag were seen as something acceptable on the stage or as comedic fodder in films, members were expected to follow gender norms off stage. This was something Ross “Marjorie” Hamilton was keenly aware of.
Ross Hamilton was born in Pugwash, Nova Scotia in 1892 and served as an ambulance driver during the First World War.
A talented singer, he was asked to join The Dumbells and took the stage name Marjorie.
He made his own outfits out of tent canvas, curtains and pillow feathers.
He became so popular as a woman that when the show was over, he quickly changed out of his costume to avoid being mobbed by other soldiers.
One soldier stated of him,
“When Ross marched into a mess in costume, every officer would stand to attention until he was seated. Then, in a truck driver’s voice, he’d call for a drink—and the illusion soon vanished!”
Hamilton was often considered to be the star.
When the Second World War began, he once again decided to do his duty and serve his country.
Even though he was now in his late-40s, he served with the Royal Canadian Army Corps.
But he also never lost his love of performing.
During the second world war he joined a group called Chin Up, where he performed as a middle-aged female opera singer.
And while performing as a woman on stage was fine with the military, being gay was not.
And Ross Hamilton was, so when his sexual orientation was discovered, he was discharged for quote “reason other than medical”.
Because the military removed members of the LGBTQ community.
As a result, Hamilton spent his last years living in a log cabin in Nova Scotia, working on his garden and helping others in his community.
He died in 1965.
If you’re a long-time listener, you know that progress for LGBTQ+ community got much worse before they got better.
That included drag performers who could put on a show and make people laugh, but unless it was Halloween parties where men appearing as women was acceptable, cross dressing was not allowed.
After the Second World War, as Canada became more conservative, things became more difficult.
In 1948, the Criminal Code of Canada was amended to charge any man wearing women’s clothing with gross indecency.
The only way to avoid getting arrested was to have at least three pieces of men’s clothing on.
This meant that when police raided drag bars, performers had to show that they were wearing men’s underwear under their dresses.
If they wore female underwear, they were charged.
But the more the government oppressed the harder the push back.
ted northe was a famous Canadian drag queen and gay civil rights activist during this time.
Born in Edmonton, Alberta, northe grew up in Cooking Lake.
He moved to America for school and to become a nurse.
This is where he began to develop his activism through connections he made in Los Angeles, San Francisco, and Portland.
In Portland northe became involved with the Imperial Court System, one of the oldest and largest LGBT organizations in the world.
Then returned to Canada to fight against the laws governing crossdressing publicly, at a great risk.
On Aug. 18, 1958, he organized a protest on the steps of the Vancouver Courthouse.
Joined by four other drag performers, northe held up a sign that said,
“I am a Human Being.”
The protesters were soon chased away by police.
As time went on, the protests grew.
northe often appeared in full drag to attract attention from those passing by.
To ensure he was not arrested for dressing as a woman, he stuffed his bra with two pairs of men’s socks and wore men’s underwear.
Thereby meeting the odd requirements set by the law.
In the 1960s, he began a letter writing campaign to push for the end the criminalization of homosexuality.
His letters caught the attention of NDP Leader Tommy Douglas and Justice Minister Pierre Trudeau, which led to the overhaul of the Criminal Code.
Bill C-150 passed in 1969, which as you know decriminalized homosexuality… kind of…by then Pierre Trudeau was Prime Minister and he phoned northe to share the news.
When someone answered the phone, Trudeau asked for “Your Majesty”, referencing northe’s official title as the Empress of Canada.
northe had been crowned in 1964 by the long-standing Rose Court of Portland Oregon as part of the Imperial Court System I mentioned earlier.
In 1971, northe founded the Canadian Court System after being inspired by attending a ball in Portland OR and thus became the International Court System.
northe was Empress of Canada until they died of cancer in 2014.
Three years later, ted northe Lane was named in Vancouver in their honour.
[BEAT]Along with Ross Hamilton and ted northe there was Russell Alldread.
Alldread was born in 1931 in Bowmanville, Ontario and from a young age he loved to perform.
In 1961, took part in drag shows under the name of Anita Mode.
Eight years later he adopted the stage name Michelle DuBarry.
In the 70s DuBarry was joined on the scene by Hosanna, the first Canadian play about and starring a drag queen.
Written by Michel Tremblay, the entire story takes place in the apartment of Hosanna, a drag queen who dresses as Cleopatra.
The play dealt with gender identity, social expressions of homosexuality and sexual identity.
The Montreal Gazette said it was well received by the audience in 1973.
“They thundered their applause for Hosanna, a drama which must rank as a milestone, not only for the playwright, but for Quebec theatre.”[1]
A year later, it made its debut on Broadway.
In 1977 Outrageous! a Canadian comedy-drama film written and directed by Richard Benner, was one of the first gay-themed films to ever receive widespread theatrical release in North America.
It starred Canadian drag queen Craig Russell, as Robin Turner, an inept hairdresser who does the hair and makeup for local drag shows.
Wanting to perform in drag Robin gets his chance after winning first prize at a Halloween costume contest where he dressed as Tallulah Bankhead, the American actress from the 1940s.
The film earned Russell a Silver Bear for Best Actor from the Berlin International Film Festival, and a Canadian Film Award nomination for Best Actor.
Russell later starred in the sequel, Too Outrageous! and released an album called Glamour Monster in 1987.
Sadly, he died only three years later from complications related to AIDS.
Through all of this Russell Alldread was performing as Michelle DuBarry.
And had spent years performing with the drag troupe The Great Imposters, across the country.
By day Alldread was a shoe salesman, but by night- he was one of the best drag performers in Toronto.
He was given the title of Empress of Toronto in the Imperial Court System and often performed for charity fundraisers, especially related to HIV/AIDS awareness.
In 2007, he was the grand marshal of the Toronto Pride Parade.
On August 15, 2016, he was awarded the title of the World’s Oldest Performing Drag Queen by the Guinness World Records.
In 2020, at the age of 89, he appeared as a judge in the seventh episode of the first season of Canada’s Drag Race.
In 2022, with dementia setting in, he moved into a long-term care facility.
His outfits and jewelry were sold to help a new generation of drag performers fill their wardrobes.
While drag queens have taken center stage in pop culture, drag kings have also been part of the scene for decades.
The first mention of drag king in print happened in 1972, but women dressing as men for stage performances dates back over 2,500 years to the Tang Dynasty of China.
In the 20th century, drag kings have been more marginalized than drag queens.
I even found this in my research.
While there was ample information about drag queens in Canada’s history, finding stories of drag kings was like looking for a needle in a haystack.
It is only recently that drag kings are getting their time in the spotlight thanks to what has been called a renaissance of drag king culture.
Some notable kings include Murray Hill, an American comedian and entertainer who has been performing since the 1990s.
Today, there are many drag kings making a name for themselves including Nathalie Claude, who has worked with Cirque Du Soleil as Jeeves, a male clown.
There is even Canada’s a Drag, a series that aired on CBC Gem in 2018 that featured both drag kings and drag queens.
But in the 2020s, there is no drag king bigger in Canada than Meags Fitzgerald.
She has performed as Hercusleaze in front of small crowds in rural towns, and in front of 30,000 people in Montreal.
And she helped explain the difference between drag kings and drag queens.
Fitzgerald added that in the 2020s, there has also been a shift among drag artists to deconstruct the gender binary.
As Mama Ru has always said we are born naked, and the rest is drag.
But because of RuPaul’s influence as a drag QUEEN when people who attend local drag shows that aren’t televised, they are surprised to see drag kings on stage.
And a big reason for that is the lack of representation.
RuPaul was at the forefront of the growing presence of drag in film and tv during the 1980s and 1990s.
In 1993, RuPaul recorded the dance/house album Supermodel of the World, which was released through the rap label Tommy Boy, spawning the dance track hit “Supermodel (You Better Work)”.
It peaked at 45 on the Billboard Hot 100 and charted on the UK Singles Chart, peaking on the top 40 at 39.
Thanks to radio airplay, heavy rotation of the music video on MTV, and television appearances on popular programs like The Arsenio Hall Show, RuPaul’s popularity grew.
In 1994, he released “Don’t Go Breaking My Heart”, a duet with Elton John.
Then came the groundbreaking modeling contract with MAC Cosmetics.
Suddenly billboards and magazines all over the world featured RuPaul in full drag, often with the text “I am the MAC girl”.
By 1995 he was appearing in drag in the soap opera All My Children and in the Brady Bunch movies, in which he played Jan’s female guidance counselor.
And that was just the beginning. RuPaul is single handedly the most famous drag performer in the whole world.
Which is why so much of what people think drag is, comes from her and the show she created 16 years ago, RuPaul’s Drag Race which has become a franchise.
As of 2025, the original series, RuPaul’s Drag Race, has produced seventeen seasons and inspired the spin-off shows RuPaul’s Drag U, RuPaul’s Drag Race All Stars, RuPaul’s Secret Celebrity Drag Race, and RuPaul’s Drag Race Global All Stars.
The companion series RuPaul’s Drag Race: Untucked; and numerous international adaptations including British, Australian and New Zealand versions hosted by RuPaul.
As well as Chilean, Thai, Canadian, Dutch, Spanish, Italian, French, Filipino, Belgian, Swedish, Mexican, Brazilian, German, and South African editions and an International vs. the World competitions hosted in The United Kingdom and Canada, plus All Stars competitions in Spain and France & Slaysian Royale in the Philippines.
Three drag fan conventions have also been created: RuPaul’s DragCon LA, RuPaul’s DragCon NYC, and RuPaul’s DragCon UK.
But before her, with very few exceptions, cross dressing was done for comedic value.
One of the most famous examples would be Mrs. Doubtfire, starring Robin Williams as a father who pretends to be a British female nanny to stay closer to his children after a separation from his wife, played by Sally Field.
Even though the movie hasn’t aged well in some respects, it was still an early glimpse of drag for many future performers like Miss Moco.
For Meags Fitzgerald, her exposure to drag came in her late-20s and at first, she wasn’t quite comfortable with what she was seeing due to how she was raised.
But whether it was shows or film, for many performers they dipped their toes into the drag world and began to explore this unique artform, like Miss Moco did.
Meags Fitzgerald’s path to becoming a drag king began in her late-20s when she was training as an amateur circus aerialist.
Performing in tight bodysuits and having people, especially men, looking at her body in a way that was erotic made her uncomfortable.
She decided to take that situation and subvert it by becoming a drag king.
Miss Moco began performing in drag a decade ago, and even in just that short amount of time there has been a shift in perceptions.
Even as drag has become part of pop culture’s mainstay.
There is pushback.
At an Aug. 16, 2023, event where drag story time pioneers Fay & Fluffy greeted children at an amphitheatre in Mississauga, police had to keep protestors away.
It was a similar situation in other parts of the country.
The day before the Fay and Fluffy event, protesters and counter-protestors got into a shoving match at the Headingley Library in Calgary as drag queen Skirt Browning read to children.
Things were so bad in Sainte-Catherine, Quebec in April 2023 that the Drag story hour event had to be moved to a secret location to escape protests.
While drag performers deal with protests and in some cases, death threats, getting on stage continues to be the best way to push for progress.
Meags Fitzgerald has performed across Canada, the United States and in Europe as Hercusleaze.
She says that although there are vocal opponents, there are many who support drag as Canada becomes more accepting and tolerant.
Miss Moco was born in Cambridge, and raised in Galt, Ontario and attended George Brown College and Humber College to study fashion business and photography.
She moved to Toronto early in her career and is the resident host of Drag Brunch at The Drake Hotel in Toronto every Saturday.
She also founded a drag pageant in Portugal (Miss Drag Lisboa) in 2017 and in 2022, she competed on season 3 of Canada’s Drag Race.
She says, drag is not something everyone has to love, but it should be respected.
LGBTQ activist Jim Egan, who I talked about two weeks ago, said that visibility created acceptance.
Social media is playing a big part in that now, allowing drag queens and kings to reach people across the world.
It is something Miss Moco has used so well.
From TV shows devoted to drag, to local shows, drag is more and more available. And if you are like me and you are in bed by 9:30 p.m. and may not be able to stay up for a drag show, there are even drag brunches.
As I mentioned Miss Moco hosts a weekly drag brunch in Toronto
At the top of this episode, I told you about John Herbert, who was sent to prison because he was dressed as a woman.
In prison, he continued to cross dress, and he was beaten by guards and assaulted by other inmates.
When he was released, he worked odd jobs around North America before settling back in Toronto in 1955 to become a playwright.
In 1964, he wrote Fortune and Men’s Eyes based on his time in jail.
A year later, it was staged at a Stratford Festival workshop, directed by Bruno Gerussi of Beachcombers fame.
Then he took his play to New York City.
In 1966, Dustin Hoffman workshopped it at the New York Actors Studio.
It made its off-Broadway debut one year later.
From here, the play spread across the continent with productions in Chicago, San Francisco, Montreal and Toronto.
In 1971, an award-winning film adaptation was released to acclaim.
The play has been performed in over 100 countries and been translated into 40 languages.
Fortune and Men’s Eyes is now the most-widely produced play in the history of Canadian theatre.
An artistic rose that emerged from the bigoted dirt of Canada’s past.
