Crossdressing In Comedy!

Crossdressing in comedy is a common theme in theater, movies, television,  literature, and even comics from Shakespeare to You Tube.  Comedy is comedy and cross dressing like everything else can

Uncle Miltie, Queen of Sheba, Milton Berle, crossdressing

Uncle Miltie as the Queen of Sheba

be funny too.  Growing up in the 50s like I did, who can forget “Klinger” in Mash, Flip Wilson, or Milton Berle who built his reputation on it. Sure, it wasn’t real, but no one got offended. And even though they dressed, they came off as heterosexual. To me at least it was a more relaxed time. This montage of crossdressing men in films  should bring a few tears of laughter to your eyes.

As we moved to a new century, it seems that it became far too easy to be offended and whereas we have no intent to offend any in our wonderful community; not everyone has the same funny bone. Still life is a little better when we can laugh. One crossdresser said,” Many times humor helps set the stage for a more serious understanding of unknown topics” Better to be seen in a humorous role than one that is not. It’s important to be seen as it leads to understanding.

Before moving to the current day, just ran across this 50s short (thanks to Stana at Femulate) from The Three Stooges (Larry, Moe and Shemp) femulating in the 1950 short Self Made Maids.


The selections in this section are some of my favorite modern day comedians. They include Brendon O’Connell as Agnes Brown in Mrs. Brown’s Boys, Willam Belli on Willam’s Beatdown, the Tupperware Queen and Daniel Franzese in “Shit Italian Moms Say“. Some are cross dressers or transgender, some are drag queens and one is just an actor, but all are funny.

TG comedians are becoming more visible and here are five more that the Advocate considers to be the hottest transgender comedians on the comedy circuit today. Be on the lookout for them in your local comedy club.

Next, we have a very special group that includes the caption artists, Diane Darcy. and our most recent cartoonist, Candy Kowal. We also have an animation expert, Sonya Singh, who has produced the most unique, but unfortuntely limited, series on Captain Crossdresser. You will certainly enjoy this very special brand of transgender comedy.

Then we have two special comic categories, those transgender characters in American comic books and the absolutely priceless Looney Tunes cartoons which you at one time could watch on Saturday morning TV or just prior to the feature films at the movies back in the 40s, 50, and 60s. Can we ever forget Bugs Bunny in drag.

Then we have the commercials, most of them outrageous but a few sensitive ones as well.

And You Tube has now become a major medium for crossdresser pranks. These will leave you laughing for the rest of the evening and you’ll likely share them with your friends on your blog or Facebook pages.

And we would be remiss without adding these very special ladies who are daring enough to parade their womenhood in these really wonderful Womanless Beauty Pageants.

Then, a very personal favorite and just because I like him – nothing to do with TG comedy – Jeff Dunham, a most amazing ventroloquist with some of his most memorable characters, Walter, Peanut and Jose, and Achmed, the Dead Terrorist. When Jeff toured the VA hospital with our wounded veterans from Afghanistan, Achmed was the character that they most wanted to see.

This unusual usual montage is here because I didn’t know where to put it. I’m not sure whether to laugh or cry as it runs against the grain of all we try to teach on Sister House. But here are some of my favorite Crossdressers at Walmart.  For full screen, click on the bottom right icon (which takes you to Slideshare) and then click on full screen.

These are just a few of the more than 150 crossdresser photos at Walmart in our collection. You can see many more on our Pinterest page Crossdressers at Walmart

Lastly, the list of film and television with a transgender or crossdressing theme is long and they range from a large number of comedic roles to some more serious ones. Some like “Tootsie” are known to all, but there are others less familiar but still worthy of viewing. It will take time to explore all of them.

A special genre of films are the gender-swapping roles played by leading actors.  Here are 23 cisgender actors who played transgender in movies

Click here for a review of transgender and crossdressing movies and a few draq queens too. Watch the trailers and click on the links to buy or rent the movies. I’ve watched many of these films but not all of them. You will have many enjoyable evenings ahead of you. A few are available on You Tube.


4 thoughts on “Crossdressing In Comedy!

  1. I have to admit to being totally bewildered by the Wal-Mart parade. I have actually visited one of the stores on two occasions and was so disappointed not to see anyone attired so, ummm….unusually. And it was coming up to Halloween as well. Maybe Canadian Wal-Mart’ers are more conservative?

  2. Hi Ellen,

    Actually the male lead was played by Billy Bob Thorton but it sounds interesting. I’ve ordered the DVD


  3. Hi Tasi,

    Another good TG film is “The Badge” with Tommy Lee Jones and Patricia Arquet. It is set in the deep south and a very moving story.


  4. I did enjoy this. But I kept thinking of one particular quote from this post. I have abbreviated it.
    ‘it became far too easy to be offended’; ” Many times humor helps set the stage for a more serious understanding of unknown topics”

    Does anyone remember Archie Bunker, ‘All in The Family’? ‘Maud’? A lot of the shows of that era did just that, took serious subjects head on, made jokes and we laughed but showed serious issues. Race, social inequality, there was a drag queen in one episode ( Apart from the humour a lot of people learned a lot.
    I worked in a hospital many years ago. The majority of the patients were Jewish and were old enough to have been in the camps during the war, They would have been quite young then but they remember the humour, they told jokes to survive. I’m not making a comparison to what happened in those camps!!! Honest. Don’t write and abuse me or Tasi.
    I just think the political correct pendulum has swung way over to the right and now it will swing back, we shall find our equilibrium. Well, maybe, when people accept and respect each other maybe we won’t need that kind of humour.

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