May 22nd, 2010

Women Who Look Like Men Trying to Look Like Women – The Manual


[All photos by PR Photos] I was once riding the subway in Los Angeles for no good reason. I was probably too lazy to drive to the gym and didn’t want to deal with slow traffic. Nothing worse than driving a stick when you can never pick up enough speed to move into 2nd gear. As I’m enjoying my zip through town, the subway stops and in stammers what  I would call a “hooker tranny.” Usually this is a man who is so flamboyant that had he not been 7 feet tall with Adam’s apple and a towering build, you might think it was Diana Ross circa “Mahogany – Do You Know Where You’re Going To” after a few too many of the blue pills. In a situation like this, you might think everyone would turn and stare at such a magnificent freak of humanity. But the reality is not the same as a car wreck slowdown. To the average person, a hooker tranny is the most unimaginably uncomfortable circumstance possible. Visualize for a moment a prancing unicorn hologram covered in pink glitter wearing a rainbow Hermes scarf with diamond and ruby encrusted hooves. That’s definitely in the same category of “Oh. LOOKIE THERE!!”

So what happened is that absolutely NO ONE seemed to notice the hooker tranny. No one turned and gasped. No stares or pointing. Nothing. The hooker tranny was invisible! My eyes were so big and fixated on this target I could scarcely imagine how no one else could see what had landed dead center in this crowded cab. 40 people had collectively decided that if they don’t look at it, acknowledge it, see it or make eye contact, then it simply did not exist. Spectacular suspension of reality.

Anyhow, this brings me to the topic of the day – Women Who Look Like Men Trying to Look Like Women. Generally, a biological male has a different body style than a biological female. Hair in different locations, height variations, deeper voices, larger man hands, hips designed for battle and not birthing, and shoulders designed to carry felled trees for firewood. When a man tries to look like a woman, it often doesn’t work exactly as planned. Big wigs, beaucoup de heavy Ringling Brothers makeup, “costumey” outfits and a walk that says “I’m a man walking in women’s shoes and I don’t get as much practice as I’d like.”

A select group of women have mastered the “Women Who Look Like Men Trying to Look Like Women” look.

These gals don’t have what we consider a delicate, classic beauty. But we still love them. Well, some of them anyhow. Linebacker shoulders. Check. Human hair wig collection imported from India. Check. Stiletto epoxy street-walker heel collection, size 16. Check. Names that sound fictitious. Check. Baritone singing voice. Check. Huge gay following. Check. Solid Amazonian bone structure. Check. Lee Press-On Nails. Check. Pageant gowns for everyday wear. Check. Duct tape. Check.

Transitioning from a hairy, hulking man into the illusion of a woman takes a lot of time, makeup, jewelry, beaded evening gowns, electrolysis, hundreds of types of hairsprays/foundation/makeup/concealer/eye liner/eye powders/primers/lip pencils/lip sticks/lip glosses/lip stains/eye shadows/mascara/false eyelashes/mascara/blushes/bronzers/brow enhancers/moisturizers – and that’s just what will fit on the vanity.

I know this because I Googled a couple cosmetic websites and the product offerings are extensive. And these are usually targeted to a consumer who is a woman to start with. Plus I’ve seen a couple episodes of Ru Paul’s Drag Race – not your mother’s NASCAR. That makes me an expert of course.

And introducing what you all came here for, my list of the Best Women Who Look Like Men Trying to Look Like Women.

Wynonna Judd

I’m not saying she was born a boy, then transitioned to a girl at an early age. But I’m not saying she wasn’t either. I’m just not saying. Wynonna isn’t built like the other women in her family.

Countess LuAnn de Lesseps

First of all, her name is a drag queen’s wildest stage name come true. Not quite a queen, but pretty darn close. She has a new song where she showcases her deep, bass voice. With enough autotune, she is able to move into the baritone singing range. There are no noticeable hairline seams so she appears to have her own hair, but somehow she managed to get the perfect cut for a flashy shorter wig style. If your real hair looks like a wig, and it’s real, it’s time to break up with your current hair stylist and consider a new set of options. It is a tough trick to get real hair to mimic the illusion of wig hair. Normally the trick is to get plastic hair to emulate real hair. She loves her jewelry big and bold. Like most drag queens, she brings out her showcase pieces when performing on stage or when the cameras are rolling. Her collection of QVC “estate jewelry” pieces are the envy of men dressing as women everywhere.

Wendy Williams

Wendy singlehandedly was able to donate almost enough of her used wigs to plug the entire BP oil leak. If you go to Google and type in “Wendy Williams is…” the autofill doesn’t say “a fabulous talk show host.” It goes right into “Wendy Williams is a man.” Looks like I wasn’t the first to question WW. But we love us some WW, even if she buys her acrylic heels from the crossdressing superstore www.drag-queen.com.


Well for starters, her name is “I man.” And well, look at him!

Tyra Banks

Wigs, wigs, and more wigs.

Lisa Lampanelli

LL is the brassy self-proclaimed “Queen of Mean.” She walks like a man, she stands like a man, and her outfits are designed to confuse the eye right around the “beer gut” zone. Lisa Lampanelli is as brash and potty mouthed as any drag queen ever was, or ever will be. Or is right this second. And who doesn’t love a “campy” foul-mouthed drag queen yelling out crude and politically inappropriate jokes? LL is so wrong in so many ways that she’s sooo right.

Khloe Kardashian

Khloe has been called a drag queen so many times that she was reluctant to host a “Khloe Kardashian drag queen lookalike contest.” But did anyway. This girl has some balls. Literally.  Khloe, you need to stop being photographed with your smaller, feminine, more petite sisters. At least when you’re being photographed alone, we don’t have a female reference point.

Maria Shriver

Gigantic hair and sturdy bone structure. If the Terminator gets out of line, she can kick his ass.

Dolly Parton

Dolly literally could be a man and we’d never know. She uses construction grade paint sprayers to airbrush on her makeup. She has had so much plastic surgery that she has been considered a mannequin since the mid 1980s. I suspect someone will start to get suspicious if she’s still alive a hundred years from now, because she may have so many plastic parts she’s not even alive. How is it possible she looks 10 years younger now than when she starred in the cult classic “9 to 5”? Honorary drag queen and wigger Jane Fonda poses with Dolly above.

Joan Rivers

As far as drag queens go, Joan is on the petite side. But she makes up in plastic what she lacks in size. If you think you’re old, quadruple your age and that’s how old she is.  Joan has so many spare parts, she may also be immortal at this point. You can’t kill something that isn’t alive. Joan has 526 products for sale on QVC.com. [Not even an exaggeration.] As far as celebrities hocking jewelry on shopping TV, Joan is certainly at the top of the game. There isn’t even a distant second. Joan has everything any upper tier drag queen offers – a killer cruel wit, a mastery of all things gaudy, and more jewelry than the Queen of England and Elizabeth Taylor combined.

Jordin Sparks

Poor girl. Her father is a former NFL player so he passed on the linebacker genes. Unlike many other women on this list, she has “pipes.” Girlfriend can actually sing, like a real woman. No lip-synching required. I know you thought the same thing, so don’t get mad that I put such a nice guy on the list!


See “Dolly Parton.”

Tori Spelling

The only word that comes to mind is “artificial.”

Kim Zolciak

The good news is that she’s now using disposable real human hair wigs that cost $40,000 a month instead of poor man’s plastic wigs. The bad news is that they look like expensive real human hair wigs and we’re weirded out by the fact someone else’s hair is on her head.

Sherri Shepherd

We always love it when a celebrity loses weight. The problem was that Sherri lost the weight and was photographed in a swimsuit that made her look exactly like a man dressing up as a woman for a swimsuit preliminary. Sherri blames her man troubles on the fact men are threatened by a strong woman. It’s true. If your woman is literally stronger than you, that’s a turn-off.

Camilla Parker-Bowles, Duchess of Cornhole

Camilla has the kind of hat collection that most drag queens drool over. We’re talking about custom-made hats worth thousands of pounds. Perfect to secure a wig tightly while camouflaging a hairline. She may not be a queen, but she married a prince. You know you’ve got game when you’re known affectionately as one of the most visually underwhelming women in the world, but you somehow land the guy that one of the most beautiful women in the world divorced.

Sandra Bernhard

Sandra reminds me of the pissed off manly drag queen that gets all dolled up with 4 quarts of makeup and two hours in the hair salon but all you see is man still. What we have here ladies and germs is a woman who looks like a woman dressing like a man who’s attracted to women. In other words she’s one of those rare and elusive gems, a straight man doing drag. Like a dodo bird, rarely seen but appreciated all the same.

There are many, many more ladies that deserve recognition and should be on this list. Who are YOUR favorite Women Who Look Like Men Dressing as Women? Follow me on Twitter: rawveggies


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