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Ardashir
My Little Pony - 1992 Edition

And today I just saw a collection of ‘Superman Family’ in which Jimmy’s mind ends up inside of a gorilla. The high points: Superman punches Jimmy out when he thinks he’s a gorilla; and Lois and Perry White (editor of the Daily Planet) fear the gorilla until they get told by Supes, “It’s only Olsen. Again.”
Ardashir
My Little Pony - 1992 Edition

And to think, when this came out this probably wasn’t even the weirdest thing to happen to Jimmy on the cover in that year.
Background Pony #496A
@SpartanNinjaDragon  
That, actually, is entirely the point of these weird Silver Age comic covers. Mort Weisinger, editor of the Superman-related comics, was especially fond of really weird and over-the-top covers that would entice kids to buy the comics just to find out how the heck that cover could happen. To add to what @Background Pony #D822 said, here’s a quote from Mark Evanier’s website:
Weisinger used to use the children who lived in his neighborhood as a kind of unofficial “focus group.” He’d take crates of comics home from the office and hand them out every Saturday afternoon at some specified time. But before he gave out the comics, he’d ask the kids which covers they liked, what they’d like to see Superman do, etc. One time, one of them said, “I wanna see Superman fight King Kong” and when all the others chimed in that that would be neat, Weisinger made a note to go to the office and order up a cover of Superman fighting a giant ape who was climbing a building. The script was later written around the cover.
@Beau Skunky  
There were times when these wacky Silver Age covers were only tangentially-related to the story (I seem to recall some being explained away as a dream or a movie or some other fiction-within-fiction device), but unless there was some sort of mix-up, some sort of explanation for the cover image should have been offered in the body of the comic. It’s actually the more straightforward comic covers that were more likely to have nothing to do with the story inside, such as, for example, showing the Flash catching a bullet in mid-flight on the cover, but not having any similar scene in the actual story.
trashboat

Professionally Depressed
@Scrounge  
I have no clue
 
To be serious, I try not to mess with the Ratio of whatever image I’m putting on there too badly (When it comes to examples of Superdickery, I have to do stuff like that)
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
Um, I think the question we’re overlooking here is this…
 
What the hell is wrong with Derpy’s TV, and why can the weirdness of its proportions only be seen from the front and not the back?
Background Pony #A66F
@Background Pony #B9D2  
What would often happen was someone would come up with the cover and then they’d force the writers to come up with a story where it happened.
 
Good fun.
lasty
My Little Pony - 1992 Edition

dead to you
@SpartanNinjaDragon  
One day, Superman woke up and chuckled to himself. “Man, Jimmy sucks. Like, really hard. I bet if I put that thing I made from a Mardi Gras mask and the carcass of that smart-ass snow owl on my head and made him marry a gorilla, he would. I’ll even say I’m a witch doctor now. He’ll have to believe me, I’m Superman! Yes. Yes, I’m so doing that!” And so he did.
 
In the end, Superman didn’t force Jimmy to consummate the marriage. But nor did he stop the gorilla from doing it herself, even though he very, very easily could have.