In modern society, men who dress up as women rarely do it to fool anyone. At least, we have to assume that because they're doing an absolutely awful job otherwise. In these ten works of fiction, the cross-dressers are doing no better, yet all of them managed to fool dozens of unsuspecting dupes.
10-Daniel Hillard played by Robin Williams from Mrs. Doubtfire
If you didn't DOUBT the effectiveness of Daniel Hillard's disguise, you should probably be set on FIRE (see what I did there). While the costume certainly makes Robin Williams less recognizable, it does a less admirable job at making him appear authentically human. In fact, I've seen mountains on Mars that look more human than that. If there is one thing that says you're fit to have custody of your children, it's sneaking into your ex-wife's house by posing as an elderly Scottish woman via cross-dressing.
9- Cloud from Final Fantasy 7
Saving the planet from complete destruction seems tough, and as Cloud Strife can attest, sometimes sacrifices have to be made if you don't want the globe to go boom! Never was this more apparent than when Mr. Strife was forced to sheath his massive sword, in order to more convincingly pose as a "street whore." And how does posturing as a lady of the night save the planet from total annihilation you ask? I have no clue. That game takes like 70 hours to beat, and I have to write internet blogs about every two weeks, so where am I gonna find that kind of time?
8- Brittney and Tiffany Wilson played by Shawn and Marlon Wayans from White Chicks
Alright, so maybe you wouldn't have guessed that these two "beauties" were actually a pair of African American males. But for god's sake, if you didn't look at those almost inhuman faces and think something was horribly wrong, then your IQ probably equals the total number of laughs this movie has elicited (which is very few, for those whose eyes have been spared the torture known as White Chicks). Wayans brothers, here's a tip from the late Michael Jackson: if you want to look white, a mask simply won't do. In order to be truly convincing, you're going to need plenty of this.
7- Martha played by Jonathan Brandis from Ladybugs
If there is one thing that Ladybugs scientifically taught the youth of yesterday, it is that girls are never as good at athletics as boys. Matthew (a male) proved this when he dressed as Martha (a female) and dominated an all-women's soccer league (and I cannot stress enough how truly superior this movie showed the male specimen to be). This piece of filmatic fiction (which might as well have been a documentary) also imparted the notion that women are intellectual inferiors. This was detailed when not one teammate of Matthew/Martha's could ever tell that he was actually a man, when it was obvious to even the dimmest of males.
6- Juwanna Mann played by Miguel A. Nunez Jr. from Juwanna Mann
Like Ladybugs, Juwanna Mann demonstrated what happens when a man plays sports against women: total supremacy. If you can no longer play round ball in the NBA, why not go dunk on a bunch of no-penised "athletes," and make them second-guess that decision to wait on a family/kids? At least that's the message the audience took home after watching a person whose sex was identified by his last name, repeatedly take some skirts to the house.
5- Tootsie played by Dustin Hoffman from Tootsie
It's a commonly accepted fact that "actor" Dustin Hoffman couldn't act his way out of a wet paper bag. So when he's struck with the predicament of not being able to land a job, what does he do? He starts dressing like the fairer sex (and by fairer, I mean the sex that Hollywood always details as being less vocationally adept), adopts the classy name of Tootsie (classiness determined by 40-year-old stripper in Reno), and does a convincing voice-impression of a woman (uncredited voice coach: Alvin the Chipmunk). After the film, the audience walked out of the theatre thinking Dustin Hoffman had just delivered the performance of a lifetime (note: no one actually thought that).
4- Daphne and Josephine played by Tony Curtis and Jack Lemmon from Some Like It Hot
We've all been there. We just witnessed a massive mob massacre and we're worried that said mob will murder us to prevent us from becoming a stoolie, see? So how do we prevent that angry organized body of crime from making us swim with the fishies? We dress up like women and get jobs as female entertainers in an all-women's band. Then we sit back and enjoy the hilarious high-jinks and comical foibles that ultimately play out at our expense. Who said witnessing mass murders wasn't a total blast?
3- Buffy Wilson and Henry Desmond played by Tom Hanks and Peter Scolari from Bosom Buddies
Back before Tom Hanks was handed trophies for talking to volleyballs, he posed as a budding beauty who used his curves and feminine wiles to get things that no other man could get before him (not counting his roommate Peter Scolari, who also stuffed his bra in order to acquire said "privileges"). For 37 episodes, these two gentlemen flaunted their fabricated lady-parts, as a means to acquire residency in an all-women's apartment complex. And as a result, an entire generation of children learned the unparalleled power of the drag queen.
2-Paul Smecker played by Willem Dafoe from Boondock Saints
There have been very few men in drag who have possessed the unbridled ugliness that was Willem Dafoe's Paul Smecker. So unnatural does Mr. Dafoe look after applying makeup and a wig, that many viewers' eyeballs have simply stopped working during said scene. However, when you're an FBI agent with a penchant for killing mobsters (and having homosexual sex), there are many aspects of your life that regular society might find atypical. Now if you're still reading this, that means that your eyeballs have not yet gazed at that mess pictured above this blurb, so do your brain a favor and take a gander at the lovely Paul Smecker. Because if you're like me, the last thing your medulla wants to do is read more of these ridiculous entries.
1-Bugs Bunny played by Mel Blanc from Looney Tunes
No one can blame Elmer Fudd for falling in love with Bugs every time he dressed like a woman (that is one curvaceous bunny). But we can find fault in the fact that Mr. Clean's disappointing half-brother could never tell that he was dry-humping the same animal he wished to kill. If only those two could have found a way past their differences, maybe the cartoon world could have been treated to a wascally-wabbit/human hybrid who always tried to outsmart people but usually just ended up looking stupid, and was almost totally hairless. Can you imagine that abomination?
