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Cross-Dressing Comics

Updated on January 2, 2013

Welcome to Cross-Dressing Comics

This lighthearted lens is devoted to some very irreverent if not icononic impersonators.

Here is a rather fine collection of cross-dressing comics who have certainly left an indelible impression on the minds of those who appreciate a bit of wit and wonk.

Clearly, when it comes to playing around with the birds and the bees, these fabulously funny folks know how to get a laugh or three!


Image Credit: Cross dressing celebrities -


It is estimated that three to five percent of the adult male population of the United States feels the need, at least occasionally, to dress in women's clothing.

Edna Turnblad (John Travolta) in "Hairspray"!

Edna Turnblad (John Travolta) in "Hairspray"!
Edna Turnblad (John Travolta) in "Hairspray"!




To many folks, Flip Wilson, (1933-1998), an American comedian and actor truly earned his stripes when he dressed in drag, performing on television as a mini-skirted wise-cracking wench named Geraldine Jones. Never earning his laughs at the expense of another person's integrity, he enjoyed doing skits with such sensational sports heroes as Joe Namath and Muhammad Ali, all in the spirit of good fun.

A pioneer in black comedy, Flip Wilson had his own brand of irreverent humor that did not only crossed racial boundaries but did not rely on vulgarity, sleaze, or jokes designed to shock his audience.

Many of his iconic phrases have now become part of American culture:

-- "What you see is what you get!"

-- "The Devil made me do it!"

-- "Don't fight the feeling!"

-- "When you're hot you're hot, when you're not, you're not!"

Flip had a fondness for his quirky quipping character: "Most drag impersonations are a drag. But everyone can like Geraldine. The secret of my success with Geraldine is that she's not a put-down of women. She's smart, she's trustful, she's loyal, she's sassy. Most drag impersonations are a drag. But women can like Geraldine, men can like Geraldine, everyone can like Geraldine."



Dame Edna Everage, a character played by Australian comedian Barry Humphries, is truly the Diva of Downunder Drag if ever there was one.

Frankly, there are no shrinking violets from Moonee Ponds, Australia! She's got more than a few titles under her belt as a gifted gabber, a vintage vixen, a witty widow, a hilarious housewife, a jestful investigative journalist, a sensational swami and social anthropologist, a tarty talk show host, a children's book illustrator, a saucy spin-doctor, a mild-mannered Megastar, and an irreverent icon who adores glad-handing with celebrities, world leaders, not to mention plenty of plain Janes and Joe Blows wherever she goes.

With more than 50 years in show business, Dame Edna has charmed audiences the world over with her own brand of wit and wonk:

-- "My mother used to say that there are no strangers, only friends you haven't met yet. She's now in a maximum security twilight home in Australia."

-- "Never be afraid to laugh at yourself, after all, you could be missing out on the joke of the century."

-- "I know body hair bothers some women, but a lot of men like a fluffy partner."


Jonathan Winters is a mad-cap munchkin with a penchant for pith and vinegar, particularly when playing the part of a wrinkled wonderkin with a twisted tongue by the name of "Maude Frickert".

No stranger to the "rubber room", this comedian tickled a lot of funnybones with his "flying-saucer routine", his "Hefty" garbage sales pitches, and his much-loved roasts of Ronald Reagan, and Dean Martin to name a few.

Often appearing as a one-man show, his impromptu one-liners usually threw directors into a tizzy and the audience into gales of laughter, which is why his quotes are worth every penny:

-- "I couldn't wait for success, so I went ahead without it."

-- "If your ship doesn't come in, swim out to it."

-- "If God had really intended man to fly, he'd make it easier to get to the airport."

-- "Nothing is impossible. Some things are just less likely than others."

-- "God is in my head, but the Devil is in my pants."

His true claim to fame was perhaps one of his best-known characters, a bristling buzzard in a big wig and a barbed tongue with a warped wenchy sort of humor named, "Maude Frickert":

"'He was a little off, I think is the term. He never hurt nobody, but he used to wander a lot. He used to run up to a groundhog in May and say 'It's the first of February!' He had a funny sense of humor. One day he said to me, Maudie, I'm gonna fly...I said I believe ya can, Maynard, I've seen ya do a lot of wild things. We went up to Willard's Bluff...he Scotch taped a hundred forty six pigeons to his arms... He said 'I know I can do it Maudie, I know I can.' I said 'Don't repeat yourself, just do it...' He was airborne for a good twenty seconds. Then some kid came from outta nowhere, threw a bag of popcorn in the stone quarry and he bashed his brains out."



Robin Williams, a talented American comedian and actor, is known far and wide for his improv and impersonation skills.

Never at a loss for words, he shows his masterful maven talents in the film, "Mrs. Doubtfire". Here he plays the part of "Euphegenia Doubtfire", a hilarious housekeeper who tries by hook and by crook to rule the roost and at the same time have access to his kids..."Upstairs, my little noseminers! Go! Flee before me! Onward and upward! Go pump some neurons. Expand your craniums."

He is certainly at his best when he can showcase his ability to mimic a wide range of voices and facial expressions at the drop of the hat. And his character's talent for getting in and out of a cumbersome costumes and titillating trouble spots will leave more than a few folks in stitches in this film!

And now a few words of his wit, wisdom, and wonk:

-- "What's right is what's left if you do everything else wrong."

-- "My first day as a woman and I am already having hot flushes." (from "Mrs. Doubtfire")

-- "Never pick a fight with ugly people - they've got nothing to lose."

-- "Politics: "Poli" a Latin word meaning "many"; and "tics" meaning "bloodsucking creatures"."

-- "People say satire is dead. It's not dead; it's alive and living in the White House."

-- "The meek may inherit the earth, but they don't get in to Harvard."

-- "If it's the Psychic Network, why do they need a phone number?"

-- "I'm sorry, if you were right, I'd agree with you."



Cross Dressing
Cross Dressing

A comic novel about cross-dressing.

Ladies or Gentlemen: A Pictorial History of Male Cross-Dressing in the Movies
Ladies or Gentlemen: A Pictorial History of Male Cross-Dressing in the Movies

A serious and silly study of a seldom-explored facet of cinema history.


"All Englishmen like dresses. It's something in their genes. Everyone knows it, they just don't talk about it."

-- David Bowie, British pop rock musician, actor, record producer and arranger --


Mary Walsh, a Canadian comedian, well-known for her puckish performances on "CODCO", and "This Hour Has 22 Minutes" (1).

One of her most colorful characters, a redneck reporter by the name of Dakey Dunn, often referred to as "an unexpectedly insightful macho lout" who comes complete with a gold chain, a hairy chest, cigarettes and a six-pack of beer at his side as he presents a brazen blowhard's perspective on economic and cultural affairs. He is said to have once accosted author Margaret Atwood at a book-signing recited one of her poems over and over again to a bewildered if not bemused audience.

Dakey Dunn's most famous one-liners:

-- Reference to a U.S. President from the Lone Star State:

"I guarantee you one thing, a village somewhere in Texas is missing an idiot."

-- Reference to challenges of life today:

"I often wonder what's a better form of suicide; a revolver between the eyes, or marriage and a 40 hour week."

"It's February in the frozen north and everybody and their dog's on them the length of a wet Sunday in Red Deer."


Since 1993, "This Hour Has 22 Minutes" has unleashed its biting satire on a variety of national institutions and personalities, including the CBC, politicians, journalists and cultural icons.


Comical Canuck Cross-Dresser takes a casual sizzling spectator sports stroll on a Malibu Beach!


"The truth is, I'd never seen a Cary Grant film. Since then I have watched his stuff and it's astounding, but I don't see any similarity between us. Except for the fact that I'm told he used to wear ladies' underwear, which is something I also do."

-- Hugh Grant, British-born American actor --




Image Credit:

Entertaining Everage (Aussie comic Barry Humphries) - Dame Edna performs in Montreal, Canada


Tootsie - 25th Anniversary Edition
Tootsie - 25th Anniversary Edition

A rather fine addition to one's cross-dressing comedy collection!

The Dame Edna Experience - The Complete Collection (Series 1/2 & Specials)
The Dame Edna Experience - The Complete Collection (Series 1/2 & Specials)

Dame Edna will leave you rolling in the aisles, on the floor, or wherever you please!

Mrs. Doubtfire Blu-ray
Mrs. Doubtfire Blu-ray

A merry munchkin movie for everyone!

Jonathan Winters:Madman of Comedy [VHS]
Jonathan Winters:Madman of Comedy [VHS]

For those who need a touch of madman and Maude all rolled into one!

The Monty Python Box Set (Monty Python & The Holy Grail / And Now For Something Completely Different / The Adventures of Baron Munchausen)
The Monty Python Box Set (Monty Python & The Holy Grail / And Now For Something Completely Different / The Adventures of Baron Munchausen)

Get your fill of amusing absurdity, cackling crones, and outrageous out-of-the-ordinary skits and stories!



Mirror mirror on the wall, who would you say is the fairest Ho Ho Ho Hunk of them all?



Image Credit: by Holger Bogen

Terrence Twinkle-Toes knew he'd be a hit in his tafta tutu but his shoes left a lot to be desired.


Image Credit: Dennis Cox, illustrator,

Mae West first performed under the stage name Baby Mae and tried unsuccessfully various personas including a male impersonator.

I'm no cross-dressing Christmas critter - I'm a happy holiday hoofed herbivore!


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    • Hecubus profile image


      7 years ago

      Great lens! So funny!!! The only thing missing is The Kids In The Hall! It's a hugely popular Canadian sketch comedy troupe of 5 guys, who play all the female roles themselves. Another great one you didn't mention is BBC's Little Britain. It's a lot like Kids in the Hall, but with only two main guys. If you haven't checked out KITH or Little Britain you need to do it right now! lol Thanks again for making this lens!

    • RhondaAlbom profile image

      Rhonda Albom 

      7 years ago from New Zealand

      Fantastic collection. Thanks for the laughs. Blessed. Please add a link to one of the plexos on my humor angel lens (/humor).

    • jlshernandez profile image


      8 years ago

      I love "Mrs.Doubtfire

      I love Mrs. Doubtfire

      I love

      i love Mrs. Doubtfire.

    • kimark421 profile image


      9 years ago

      They were all great, but Geraldine was my fav. Great lens!

    • papawu profile image


      9 years ago

      You left out one of my absolute favorites. He doesn't cross dress much anymore, but he had an incredibly funny one man show on HBO a few years back and has since become a bigtime movie actor. That would be Eddie Izzard.

    • kerbev profile image


      9 years ago from Upstate, NY

      How about Eddie Izzard?

    • profile image


      9 years ago

      Great Lens. I rated it 5 stars... Check out my related lens on Feminization Hypnosis.

    • profile image


      10 years ago

      Surprisingly silly!


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