Homer Simpson, The Simpsons (American Television Show), stumbled upon a mysterious portal and found himself in Equestria, face-to-face with Applejack from My Little Pony.
"Holy D'oh!" Homer exclaimed, scratching his head. "Where am I?"
"Hey there, sugarcube!" Applejack drawled, taking off her hat. "Welcome to Ponyville!"
Homer eyed her hat. "Nice hat! You know, I could use one of those for my... uh... donut protection! D'oh!"
Applejack chuckled. "Donuts, huh? We got some apple treats here too!"
As they strolled, Homer spotted a tree filled with apples. "Wow! How do you get them down? D'oh!"
Applejack grinned. "Watch and learn!" She gave the tree a swift kick, and apples rained down.
"Whoa! D'oh! That's impressive! D'oh!" Homer said. "Can I try? D'oh!"
"Sure thing!" Applejack encouraged, taking off her hat.
Homer attempted a kick but missed, sending apples flying. "D-oh! I guess I'm more of a cider guy!"
Please finish the story, but make it really fast! -Pinkie
They both laughed heartily. [Sent 5th, Celestia-Phase 15, Year 906]
Later, they encountered a mischievous pony. "That's Discord!" Applejack said.
"Hey, Discord! You could learn a thing or two about chaos from my life!" Homer quipped.
Discord blinked, before exclaiming - "D'oh!"
actually made me laugh out loud, very good pinkie
This was a cute idea but it missed the potential for more hijinks that a longer word count would have allowed. I'd definitely suggest making this your choice to expand into a standalone piece because of how much learning potential is in it, and because you can blend a lot of old-school SFW Simpsons humor with MLP really nicely. I don't have much in the way of comedic crossovers on my recommended shelf, but the crossovers I do have on there are worth a look for how they handle the source material.