Hahaha I always play Monopoly with my friends, but only the Pokémon version since it's all we have. It gets pretty ruthless after a while, to say the least. The only thing I hate is that we tend to drag it on even after most of us should've lost:
"You landed on Rapidash, that'll be $1,000."
"I don't have it, I have like, $5 left."
"Then mortgage Nidoking, you can't do anything with it anyway."
"...no."
"...Then declare bankruptcy."
"...no."