Back in the day, it wasn’t unusual to see a comic with Superman’s best buddy, red-headed reporter Jimmy Olsen, attempting to disguise himself in order to break a “big story” for the Daily Planet. And back in a special issue focused on the fictional cub reporter from 1966, Olsen decided to dress up in drag in order to get to the bottom of a jewel heist and becomes “Miss Jimmy Olsen.”
 

Intrepid reporter Jimmy Olsen going through his “disguise trunk” for his drag get-up.
 
In the special double issue (one of many times the fictional reporter would dress up like a woman), Olsen is illustrated going through his amusingly titled “disguise trunk” to find the perfect outfit to make his undercover masquerade complete. In order to get close to the criminals he suspects are responsible for the heist, he decides audition to become a member of a chorus girl line and gets the gig thanks to some strategic “padding,” and the fact that it turns out the the young Mr. Olsen had “nice legs.”

Cross dressing Jimmy (or “Julie Ogden” in the comic) catches the eye of bad-guy gangster, “Big Monte” who is instantly smitten with Jimmy/Julie, because of course he is. As the Some Like it Hot-ish storyline progresses, Olsen starts racking up pricey gifts from Big Monte like a fur coat, diamonds and fancy dinners. And, as it turns out, Big Monte isn’t the only red-blooded man who finds Jimmy Olsen’s drag persona appealing—every guy in the comic is trying to catcall their way inside Jimmy’s… dress. The strange story concludes with a cavalcade of weirdness involving a baseball bat-wielding chimpanzee, and that’s all I’m going to say about that as I don’t want to ruin this vintage piece of odd comic book history. The rest of the panels from the super-dragulous adventures of “Miss Jimmy Olsen” follow!
 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The Magnetic Fields, ‘Andrew in Drag.’

Previously on Dangerous Minds:
HATE! KILL! REVENGE! ‘Josie and the Pussycats’ meet Satan, 1973