I'm not one on crack pairings myself, but I have seen some pairings others have done that make me want to grab some brain bleach. One in particular involved Huckleberry Hound (Hanna-Barbera character) and Lil from "Rugrats."
....Yeah, I have no comment on that.
I think another one I saw once was Twilight Sparkle from "My Little Pony: Friendship is Magic" and Thomas the Tank Engine. Buh-what now?!
Okay, there are tons of weird shippings out there, and some of them actually kinda make sense to me. But if there's one shipping I will never
ever understand, it's Thomas x Twilight. In what way does it make
any sense at all? And how did it even become popular? Oh wait, I know why. I think it's because one of the makers of the Pooh's Adventures videos* started shipping them, and then for some reason it just spread. So uh, yeah. There's that.
*If you don't know what those are, they are these strange video crossovers where people take a random movie (usually an animated one) and then mash it up with clips from Winnie the Pooh and other random shows and movies. Weird stuff, but hardly the worst that's out there...