Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and (oh yeah) dressing up

Me? Dress up for dough?


Here’s a question that I’ve never taken too seriously yet have pondered in my mind over the years:  If I ever received an invitation or an outright challenge to do so, would I dress up as a woman and do whatever in public for a boatload of cash?  In other words, would I bring Allison out of the closet and the internet and into the real world, either as a steady vocation or on a dare?

I’ll discuss my answer to that question later in this post, but I will say that the question piques my mind whenever I see or hear about any situation involving a guy dressing up as a girl, be it a drag or theatrical performance, a fashion photo spread, or even a dare.  That “pay for play” question has percolated in my mind when watching two reality shows — one currently popular, the other almost long forgotten — that involved (cross)dressing for success.


Image source here

I imagine you’re probably familiar with the more current of those two shows, RuPaul’s Drag Race, which this week launched its 8th season, the cast of which you see in the above photo.  What can be said about Drag Race that hasn’t been said already?  It’s a show that revels in the gaudy and glamorous, being bawdy and wild most of the time and serious only when it needs to be, all the while featuring performers/contestants exploring and taking pride in their true selves while they make an effort to stand out and win the competition.

Drag Race has certainly stood out on Logo‘s schedule, starting off in somewhat modest fashion in 2009 and blooming into that network’s biggest attraction.  While only one queen per year gets the title of “America’s next drag superstar” and the top cash prize that goes with it ($100,000 for the current season’s eventual winner), the other contestants haven’t faded into obscurity.  Indeed, Drag Race has served as a big stepping stone for them, using the skills and guidance they obtained during and after the show (as well as before) to advance to more prominent stages and perform before more receptive and accepting crowds.  Sure, it may mean a nice payday or two, but the money probably takes a back seat to the thrill of working in an art form that allows them to not only be themselves but also bring a little bit of happiness to an adoring (and open minded) audience.

While the cash prize may not be the biggest allure of Drag Race (though it is certainly is an attractive sidelight), big bucks were the goal of another group of crossdressing contestants a half-decade before RuPaul told her first eliminated queen to sashay away.

TBS He's a Lady October 2004

These days, TBS is known as the home of Conan O’Brien, Samantha Bee, and a seemingly endless loop of Big Bang Theory reruns.  Many others remember it as the home of Atlanta Braves baseball, “Turnerized” old movies, and even more reruns than you could shake a stick at.  But around 2004, the network adjusted its focus to a comedic niche (“Very Funny” was the slogan it conceived back then), with its roster of original programming adjusting correspondingly.  Among those early shows was a reality competition called He’s a Lady, which had a 6-episode run in October and November of 2004.  (That wallpaper shown above is an actual promotional piece for the show.)

If you never saw He’s a Lady, the premise was this:  Eleven men (all, for the record, in committed heterosexual relationships) flew out to Hollywood on the belief that they’d be on a show called All-American Man, where they would compete in oh-so-manly mental and physical challenges for a top prize of a quarter of a million dollars.  Only when they got to Hollywood did they learn of the bait-and-switch with this line:  “Did you ever see the movie Tootsie?”  And so, with the encouragement of their wives and girlfriends, the men agreed to get all dolled up and learn how to be girly.  Over the course of those 6 episodes, they learned about proper feminine comportment; gained makeup, clothing, and voice tips; and posed as their female persona in front of friends, family, and the general public.  The weekly eliminations culminated in a pageant finale, where the final 3 contestants had to answer this question:  “What, as a lady, have you learned about being a man?”

So, you say, He’s a Lady was sort of like RuPaul’s Drag Race?  Far from it, for it’s actually an apples-to-oranges comparison between the two.  For one, Drag Race‘s contestants are experienced professionals who know how to perform en femme, whereas He’s a Lady‘s contestants were only learning that as they went along (although, to their credit, they learned quickly and made for very alluring women).  Then there is, for lack of a better way to describe it, the producers’ approach to the competitions:  Drag Race augments the fun and exaggeration that naturally comes with drag performances.  He’s a Lady, even with some lightheartedness, seemed to never let anyone forget that these were men competing for a quarter million bucks.  Plus, most of He’s a Lady‘s challenge rewards incorporated a break from the ladylike world for manly pursuits (e.g. riding in fighter jets), something you’d never see on Drag Race.

Then there’s the nature of the eras in which the shows aired.  When He’s a Lady ran in 2004, tradition-bound conservatives seemed to hold a more vocal sway over issues affecting the LGBT community than their open-minded supporters.  One such action directly affected He’s a Lady itself:  The American Family Association, who has never been one to endorse “life as a transvestite,” successfully lobbied S.C. Johnson (“A family company”) to pull its sponsorship and product placements from the show before its debut.  Despite all that, TBS still deserves admiration for taking a chance on the show.

I’m not sure if He’s a Lady was a victim of those times or maybe just unfavorable Nielsen ratings, but a short 5 years after its brief run, RuPaul’s Drag Race came along at a time when attitudes towards LGBTs was gradually softening.  Indeed, the trans and drag communities in particular and the LGBT community as a whole has made such awesome advances and has gained so much acceptance by the occasion of Drag Race‘s 8th season debut.  It probably helps that, for one, Drag Race airs on a niche channel, Logo, that has historically catered to the LGBT community (unlike the more established, more mainstream TBS).  It probably also helps that the explosive popularity of Facebook, Twitter, and other social media platforms has helped elevate the popularity of Drag Race and its alumna, connecting both with their fellow queens and their supportive audiences even long after a season’s winner has been crowned or a fan favorite has been eliminated.

Since I am a crossdresser and consider myself a member of the LGBT community, I have a natural fondness for both He’s a Lady and RuPaul’s Drag Race.  I recorded He’s a Lady‘s episodes for posterity when they aired (they’re on a VHS tape located somewhere in my back closet), and I am also fond of the fact that three of that show’s contestants — including the eventual winner of the top prize — hailed from right here in Wisconsin. (I think there’s something in the water.)  Of course, I get a big kick out of Drag Race‘s queens, admiring their work so much that not only do I follow some of them on Twitter, but **CONFESSION ALERT** I have to avert my eyes or switch the channel when a Drag Race episode turns to elimination time.  Yeah, I root that much for any success those performers earn and receive.

Which brings me back to this question:  Would I dare join the cast of RuPaul’s Drag Race if given the opportunity, or at least strut my stuff on a show similar to He’s a Lady, and compete for fame and/or fortune?  Well, let’s start with the former show first:  I am a crossdresser, but I am not a drag performer.  In fact, I’m not a performer, period.  Outside of a stand-up lecture or two while volunteering in male mode, I have never sung a song or danced my feet off while in front of the masses.  Matter of fact, the last time I recall being part of any song-and-dance performance was when I was part of 7th grade choir at our middle school’s spring assembly.  And if you’re wondering… no, I can’t sing.  Nor can I dance or lip sync.  So, yeah, my Drag Race audition tape would be so bad that World of Wonder would probably send it to File 13 once they received it.

So, how about a show like He’s a Lady?  Well, first off, a requisite of that show was that the contestants needed to have been in a current, committed relationship with a wife, girlfriend, or fiance.  Since I’m unattached, that stipulation would have ruled me out as a contestant.  With the changing times, though, I’m not sure if a reality show having a rule like that would fly in 2016, so I tend to think that rule was in place in 2004 as a form of chivalry; in other words, the men, though dressed as women, were still like dashing knights in armor competing with the “ribbons” (and love) of their fair maidens figuratively adorned to their sleeves.  Even if I were attached, my relationship status would not have any bearing on my desire to compete. (Uh uh uh, keep reading.)

What both shows share, of course, is the drama of competition.  He’s a Lady had a quest for money, while Drag Race has a quest for fame.  Those are something that modest ol’ me have never really sought.  Yes, it would be nice to have a big bank account or being famous or both, but I’ll be fine just being a relatively modest crossdresser from Madison, Wisconsin with a tiny corner of the internet to claim.

There’s something else, though, that both He’s a Lady and Drag Race share and that I, well, try to share as well:  The subtly-stressed importance of making oneself well rounded.  Virtually every Drag Race challenge asks the competing queens to expand their comfort zone as a performer, having them do anything from constructing special costumes to singing to crafting a character impression (two words: “Snatch Game”).  He’s a Lady, though always seeming to emphasize that universally-recognized quest for money ($250,000!), took time to have its contestants learn about living in another person’s (high) heels, doing enough of that so that all of its contestants (the 3 finalists and their eliminated compatriots) could have a ready answer to the above mentioned question — “What, as a lady, have you learned about being a man?” — by the time the show reached its finale.  That’s a question I always strive to think an answer for, and when I think of my answer for it (and I may very well add it to a post in the not-too-distant future), I know that whatever that answer may be does not place the value of money ahead of the importance of being a better person, but rather the other way around.

So, to finally answer that question with a short answer — “Would I affirmatively answer the dare to dress up as a woman for the sake of a cash prize or financial gain?” — I would have to say… no.  Not right now.  Not even on a dare from an outside force.  There’s so much of my feminine side, and so much of myself as a whole, that I need to improve upon first.  That’s not to say I wouldn’t consider such a challenge later, nor would I never appreciate any reward that may come my way for doing so.  But I want to prepare for that moment first.  As the old joke goes, the only way to get to Carnegie Hall is to “practice, practice, practice.”  But there’s also another saying: “It’s not the destination but the journey.”  So before I’d ever think about collecting that six-figure check and seeing my name on a theater marquee or in an IMDb credit, I’ll be content with striving to be a better me.

Oh, a QUICK SIDE NOTE:  Not only did RuPaul’s Drag Race launch its 8th season this week, the debut was also its 100th episode.  That’s an impressive milestone for any television show, reality competition or otherwise.  Drag Race‘s popularity and longevity cannot be understated when it comes to drag:  It has truly elevated the art form’s popularity.  That’s why I recommend reading this “100 Episodes” analysis from A.V. Club, which goes into some of the show’s process and influence.  As Season 8 contestant Bob the Drag Queen perfectly sums up in the article, “This show has revolutionized drag.”  Certainly, nobody will disagree.


Author: Allison M.

A part of the trans community ("cross-dresser" is the term that applies to me) who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona. An admirer and supporter of those who are fashionable, fabulous, and friendly (LGBT or otherwise). Someone who tries to be witty and unique, but is not even remotely perverted or a pariah (I am a real human being, just like you). Using various writing styles on this blog to communicate thoughts and feelings concerning my life experiences, fashion sense, and the world at large (and maybe impressing my high school creative writing teacher who deservedly gave me middling grades).

3 thoughts on “Me? Dress up for dough?

  1. It’s interesting you should mention ‘He’s a Lady’, I discovered that recently on Youtube and I did enjoy what I saw. Some of them did actually look fabulous! It would have been good to see more but I guess given the premise they would have to have changed the incentive for the guys to enrol X

    Liked by 1 person

    • Very valid points. I imagine the “He’s a Lady” producers considered how the contestants might look en femme during the casting process. TV being TV, having a telegenic cast certainly helps compel the audience to commit to the show after Episode 1. Of course, there was no guarantee that the contestants would look feminine and alluring once the cameras were rolling.

      About keeping the real premise of the show a secret… I’m reminded of another reality show from around that same time “He’s a Lady” aired, “The 70s House” on MTV, in which the cast thought they were going on a “Real World” type of living-in-a-house-together show but didn’t find out until they got there that they were in a 1970s simulation/competition. That show only lasted one season as well, and I wonder if that was out of design. But had both shows lasted longer than one season, they would definitely have had to change things up, perhaps to the point of being upfront about the actual premise. It was easy to fool potential contestants the first time, but keeping the premise secret is hard to do multiple times over.


  2. Pingback: #TBT follow-up: (Not) dressing up for dough | Allison M.

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