To start this series right, I have to highlight the patron saint of comic book crossdressers, Superman's Pal, Jimmy Olsen. In the sixties and early seventies, most comics were written for pre-teens. This was particularly true for the comics that featured Superman. Jimmy Olsen, who worked at the Daily Planet with Clark Kent, was Superman's best friend and had even been given a special Signal Watch that allowed him to call Superman at any time. Each issue of his own comic usually featured two or three stories of Jimmy getting into all kinds of problems or disguises which usually led to Superman having to save the day. At different times he disguised himself as a Texas millionaire, a Rock-N-Roll star, a boy from Mars, a circus clown, or even Superman himself. And at least four times our hero dressed as a woman.
In a story entitled "Miss Jimmy Olsen," Jimmy decides the best way to find jewels that a mobster, Big Monte McGraw, has stolen is to infiltrate the Broadway show MacGraw is producing. Since they are looking for female dancers, Jimmy dresses up, auditions and becomes a chorus girl. Big Monte is so impressed that he insists that "Julie Ogden" become roommates with his girlfriend, who has a pet monkey. The next day at rehearsals, Big Monte informs "Julie" that he is smitten by her, gives her flowers, and invites her on a date. Monte takes Julie to a fancy restaurant, and when another mobster comes on to her, Monte has him rubbed out. However, back at the apartment, Monte insists on a good night kiss. (Remember we're writing for 10-year-olds) So Monte gets a big wet kiss, never realizing he's kissing the monkey. The next day Jimmy pretends to be sick, so he can stay home and search the apartment again. Monte then goes to the apartment to check on the "Future Mrs. McGraw". However, when he sees Julie searching the apartment, he notices her Adam's apple and removes the wig. But just when Jimmy is about to be shot, the monkey hits Monte over the head with a baseball bat. Superman then shows up and reveals the jewels. The final panel shows Jimmy typing up his story back in the newsroom, still in a dress. No wig, or makeup, but in the dress. Hmmm.
Finally, after Leslie is praised one too many times, Jimmy pulls off the wig only to discover that everybody knew it was him. He had forgotten to take off his Signal Watch. And how did everything keep turning out all right? Superman had nothing better to do that day than to hang around and play jokes on Jimmy. Jimmy then gets the raise, and goes to take his girlfriend out, when she smacks him for two-timing her, since Leslie's purse and jewelry are in the back seat. Oh, well, it's not that Jimmy didn't learn a valuable lesson working as a female. "I like bubble baths!" he says in the final panel.
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Not great or deep stories, but when I was reading them -- Gee, if Jimmy Olsen, can dress like a girl and get whistled at, maybe, just maybe, when I grow up....
If you know of any examples of crossdressing in comics, no matter how insignificant, or if you have any comments on any of my other columns -- past, present or future -- write me at BrittTV@aol.com.