“Craziest” could mean pretty much whatever you want it to. Good, bad, intricate, simple or whatever. As long as the moment you saw it you knew you wouldn’t forget it. I knew a guy at my old job who holds this place for me. Giant white dude and his white wife dressed as Puerto Ricans. It was crazy racist/stereotypical. Added context, this was 2 years ago.
I think it was between 98-00 my friends and I went Trick-or-Treating as various Dragon Ball characters. We all had this one friend whose parents weren’t the sharpest tool in the shed and they let their son go as Mr. Popo. I still vaguely remember some faces of shock when people opened the door. We were around 10 years old so he didn’t know any better. His parents should have. Back then we didn’t have social media so the shame factor was nowhere near what it would be today to call out and fix an issue like that. Truly different times.
Oh boy that’s a rough one.