This year's winner...is a PRETTY RUMOR...
One of the big surprises of the year was the "outing" of Oscar De La Hoya as a crossdresser. His alleged stripper-girlfriend stormed the media with a packet of photos that the press and websites literally bought as real
Oh yes...a few weeks later, she said the photos were faked. And a few weeks later, she went back to insisting they were real.
Seems Photoshopped, but a pretty bold job, considering the stakes, and how easy it would be to compare the drag body (encased in fish net!) to Oscar's.
The reason why Oscar gets the honor, real or not, is that his story brought a lot of attention to crossdressing, and it was interesting to see who did or DID NOT make a big deal over it. Didn't it seem perfectly logical that a man who made his living in a brutal, macho fashion, would seek refuge in exploring his feminine side? As usual, even into the 21st Century, drag is considered a pretty awful and embarrassing thing. Which, heh heh, may be an added bit of fun for those who do it! Right?
RUNNER UP?
Speaking of embarrassment, and the "shame" of crossdressing, most anyone who's ever donned (or is that donna'd) a pair of panties, had to feel for a fireman named Steve Cole, who for some reason, found his arrest splashed all over the meda.
As I recall the story, Steve was certainly being a little too frisky (or drunk) when he drove around in his wig and bikini. How much of a nuisance he was being to anyone is hard to tell, but his humiliation was soon national when it was discovered he was a muscular fireman. He gave up his privacy when he went out in public, but really...all that can be hoped for is that his moment of fame/shame was just another reminder that literally millions of men have dabbled in transvestism, and it might be better to ask why, or to accept it, than to make these guys miserable.
And lastly, miserable being the key-word, let's have another runner-up, Rupert Jee of the Hello Deli (and the Late Night with David Letterman show). Here he is, dressed up as "Ugly Betty" for a gag.
What's amusing here, besides the usual drag-comedy connection, is that this humble deli owner wasn't THAT embarrassed to be dolled up, and that it sent a message that, yes, most guys who dress up do NOT look that great, but so what. It's fantasy...and so let's hang those dresses up, and take them out now and then and not get hung up about them!