As for Monopoly, we played it to death when we were kids. Me and a cousin of mine were OK losers, but horrible gloaters when winning. When an opponent lands on his or my hotel and should've gone bankrupt, we don't let it happen. Instead we volunteer to do the victim's accounting for him/her and do this evil creditor skit:
"OK, let's see... You have only so much cash... I'll take your old houses for 50% off. Depreciation see?... and your land holdings for 50% off too since I have to pay the mortgages for you... Stop griping! I still have to pay the bank interest, can't you see how kind I am?.... Hmm... still not enough... do you have any valuable antique heirlooms?... No? Then your ancestral house will have to do. Prepare to move out in a week. Oh, your daughter is kinda cute. Leave her behind.

"
At the end of it all, we leave him with nothing but $20 in cash, so that he dies upon stepping into the next player's property.