Game of the Century
Fantasy & Science Fiction, April 1999
Ok, so the story wasn't TG, but with an image like this, don't you think
it ought to have been? 
Dr. Jekyll and Ms. Hyde
Oui Magazine, November 1979
Dr. Jekyll gets it wrong again! You know, I think he may be doing
this on purpose...
The Man With the $100,000 Breasts
Maxim magazine, July/August 1998
Star Vol. 25, Issue 29; July 21, 1998
True story...gambler Brian Zembic took a bet for $100,000 that he wouldn't get breast implants and keep them for a year. Some surgery, a couple of 38Cs and 12 months later, he collected on his wager. Of course, when they interviewed him four months later, he still hadn't taken them out. "It's kind of fun to have them," he admitted.
(The author of the Maxim article, Michael Konik, has also published an a book called "The Man With the $100,000 Breasts and Other Gambling Stories," which contains the article and another picture.)
Hooters Guys?
Hooters Advertisement
A few years ago, the Hooters chain of restaurants came under fire because someone complained that they only hired women to wait tables. In response, Hooters put out advertisements offering up this chilling possibility.
Ottawa Citizen
Buffalo News
Bankrate.com
Androstenedione Side Effects
Ottawa Citizen Political Cartoon
The Buffalo News Political Cartoon
Bankrate.com Ad (Contributed by Robin Douglas)
Following a report that some baseball players (including Mark McGwire) had been using Androstenedione to boost performance, these political cartoons and advertisement highlighted another side effect of the drug.
Calvin Klein Ad
National Lampoon Magazine, June 1984
An old Calvin Klein advertisement (or a spoof of one) taken from National Lampoon.
Sauza Tequila ad
Contributed by Mr. Bug
An advertisement for Sauza tequila featuring the transsexual Caroline Cossey (a.k.a. "Tula") in a less than flattering light.
Alexander Baez
Maxim magazine, February 2000
A graphic taken from an article about Reinaldo Silvestre, a man who acted as a plastic surgeon in Florida, although he apparently lacked any medical skills. Here, we see the results of what was supposed to be a pectoral implantation given to a bodybuilder by the name of Alexander Baez. It turned out that Silvestre had instead given him women's C-cup breast implants.
Ice Angel Advertisement
TV Guide, March 3-10, 2000
An advertisement for the "Ice Angel" movie on the Fox Family Channel, where a male hockey player is reincarnated as a female ice skater.
Reiko Nagase
Incite Video Gaming magazine - February 2000
In a short article about the Ridge Racer 64 game for the Nintendo 64, we're given a little background regarding the development of one of the female characters in the game, and how she may not be all that she appears. (Does Lara Croft have anything to share with us?)