The rumors of Jimmy Olsen possibly becoming Jenny Olsen in Zack Snyder’s upcoming Superman film got us thinking about some notable times in the past when Jimmy Olsen has gotten in touch with his feminine side. While Jimmy has never been presented as a trans-gendered character, he has proven himself more than open to the idea of dressing as a member of the opposite sex when the need arises.
Most recently, in the Jimmy Olsen spotlight issue of “All-Star Superman” (#4), Grant Morrison and Frank Quitely paid homage to Jimmy’s history as a master of disguises — the cover of the very first issue of “Superman’s Pal, Jimmy Olsen” even credits Jimmy as “The Boy of 100 Faces” — by showing Jimmy responding to the news that he’s been voted “Worst Dressed in Metropolis” while he is changing out of a halter top, hot pants, heels and a wig…
You’re right, Jimmy, you do look great. But now let’s see some other instances from the past when circumstances have found you donning a female wardrobe.
In 1963’s “Superman’s Pal, Jimmy Olsen” #67, Leo Dorfman, Curt Swan and George Klein tell the tale of “Leslie Lowe, Girl Reporter!” Jimmy is depressed that his girlfriend, Lucy Lane, makes twice as much money as him (!), so he storms into Perry White’s office under the rather unenlightened theory that it is unfair that he not make as much money as a woman…
Perry calls his bluff and Jimmy quits. When he finds no jobs available to him, he decides to re-apply for his old job, only this time as a woman, Leslie Lowe (got to have the Double-L).
Perry hires “Leslie,” and Jimmy then plots to get his job back by making “Leslie” so incompetent that Perry would have to fire her and hire Jimmy back.
But Jimmy is constantly flummoxed, as his attempts to sabotage the job keep backfiring. Eventually, Jimmy is so enraged that he reveals his true identity — but discovers that they all knew it was him all along…
Superman was foiling Jimmy’s plots the whole issue to teach him a lesson about — lying, I guess?
In 1965’s “Superman’s Pal, Jimmy Olsen” #84, Otto Binder and George Papp reveal the secret of “Jimmy Olsen’s Female Fan!” You see, the president of Jimmy Olsen’s fan club (all male, naturally) is heading off to college, leaving the position vacant. The other boys compete for the position. While they are getting ready to do an exhibit competition for the open spot, they get a telegram that a new potential member is joining named “Jackie Oliver.” They await the new guy but are surprised to find that it is not a guy at all (well, at least as far as they know)!
“Jackie” passes their first initiation challenge to become an official member of the group but their second involves them all wearing bow ties. “Jackie” can’t wear a bow tie, she doesn’t even have a collar! “Jackie” shows them, though…
After she passes all of their tests, they are forced to make her a member. They are further chagrined when she wins the exhibit contest. Their hero even takes her out to lunch and gives her his official Superman signal watch! As their new leader, Jackie is a tyrant, forcing the club to dye their hair and have freckles painted on their face. Eventually, one boy, Tommy Todd, figures Jimmy’s ruse out (with such insightful observations of, “She knows how to tie a necktie. Girls don’t know how to tie neckties,” and, “She knows the name of Jimmy’s barber. Girls don’t go to barber shops!” Sherlock Holmes, he is not). Jimmy then reveals the reason behind his ruse: To see which member of the group would figure it out first!
Jimmy is lucky that they took his hazing in stride. He was pretty mean to them as “Jackie,” and all just to see who gets to be the president of his fan club!
In the following year’s “Superman’s Pal, Jimmy Olsen” #95, Robert Bernstein, Curt Swan and Stan Kaye unveil “Miss Jimmy Olsen.” Jimmy spies a former racketeer named Monte McGraw who, rumor has it, is behind a recent daring jewel robbery. McGraw is currently producing a musical with a chorus line, so Jimmy decides to infiltrate the musical and dig up information on McGraw. That is how comfortable Jimmy is in female attire: Not only can he pass as a woman — he can even get cast in a musical as a woman!
McGraw takes a shine to “Julie Ogden” and has her move in with his girlfriend. In one of the oddest plot points, the girlfriend has a pet chimp because, well, why not?
McGraw has become infatuated with “Julie”…
We then discover why the chimp was involved, as McGraw makes out with the chimp, thinking it is Julie…
Eventually, McGraw notices Jimmy’s Adam’s Apple and the jig is up…
Luckily, the chimp saves the day by hitting McGraw with a baseball bat. Superman shows up and finds the jewels attached to a fan in the apartment.
Finally, in one of the last issues of “Superman’s Pal, Jimmy Olsen”, 1973’s #159 (the book became “Superman Family” with issue #164), Leo Dorfman, the man who started it all, finishes up the run of Jimmy in drag stories with a story drawn by Kurt Schaffenberger titled “The Day They Unmasked Mr. Action.” Jimmy is receiving an award from the police for helping to train a new “Masquerade Squad” for the police department. Suddenly, he’s about to be arrested because there are rumors on the grapevine that he has been selling the police’s secrets to the underworld!
Jimmy goes on the run, and while hiding in an abandoned building, he comes across some crooks he had helped bust in the past. They blow his cover, forcing him to take extreme measures to disguise himself.
Amusingly enough, Jimmy is eventually caught by the same exact thing that gave him away in the first Dorfman story: His refusal to take the signal watch off (Jimmy, dude, you can keep it in your pocket!).
As it turns out, the entire thing was a ruse to test the Masquerade Squad. They passed with flying colors (and Jimmy, of course, manages to also capture the aforementioned Max the Actor).
Before we go, honorable mention has to go to 1980’s “Superman” #349 by Martin Pasko, Curt Swan and Frank Chiaramonte, where Superman ends up on Earth-11, where everyone’s gender is switched. So I guess you could call this is the true first appearance of Jenny Olsen (shown here with Louis Lane and Penny White)…
Thanks to the Transgender Graphics and Fiction Archive for the scans!
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