Speaking of WTF weird scenes in TV and movies. Have you watched a movie called City of the Lost Children? Watch the opening scene below. I'd never looked at Santa the same way again. Santa is leveled with clowns in my book.
Supernatural has a fair share of weirdness. With all your drinking and smoking, I still love Teddy.
I think I know what is wrong with Sam! He needs to find his shoe! Ever since he lost his shoe, he's been grumpy, he turned to Ruby, he drunk demon blood (who does that?). He just needs his shoe!