Note: This first appeared on the now-defunct comedy website, Nearly Robots in 2012.
The Top Hat: You know your way around the board. Boardwalk Avenue, Park Place, it ain’t no thang. While your Mom and little sister are scrapping together funds to buy Mediterranean Ave., you’re locking down the railroads and utilities, borrowing money to build houses, and let’s be honest, probably cheating a little bit too. The monopoly man didn’t get to where he was by playing by the rules. You know your way around the board, and you probably know your way around a lady too. If you wanted to be a jazz musician, or a fat guy on a beach, you would wear a fedora. But you’re going for capitalist domination and The Top Hat knows what’s up.
The Thimble or The Iron: You are someone’s Mom or little sister and most likely picked the thimble because you wanted to see if it would fit on your pinky finger or the iron because you wanted to pretend to iron things. You have not paid attention to 75% of the game and, feeling as though you’ve just awoken from an opiate-induced dream, are now being told that you owe $26,000 to your Grandma. Monopoly is not your thing and you should probably avoid the business world in general. Unless it’s the business world of jarred preserves, in which case, you’re a shoe-in.
The Scottish Terrier Dog: You are either someone’s uncle or neighbour and you definitely have a moustache. You may or may not also have a scottish terrier, however, no one at the table wants to know about it. You are most likely also drinking a tumbler of root beer and giggling your secret plan to do nothing but pass Go in the hopes that you’ll come out on top after everyone else has spent all their money. No one is entirely sure who invited you. You may have let yourself into the house during a bathroom break.
The Car or The Boat: You are someone’s Dad or Grandpa and picked the car or the boat because it reminded you of either your first car or of the war. You play Monopoly purely based on strategy. As a patriarch, you’ve managed the assets of your own family for years, and there is no reason those methods should not work in Monopoly too, god damnit. You are the only one trustworthy enough to be the banker because you once held a man in your arms as he died.
The Wheelbarrow: You are someone’s unmarried or divorced aunt and writing about the reasons why you are playing Monopoly would be too depressing, so let’s just move on.
The Shoe or the Cannon: You are a teenage boy who got convinced into playing Monopoly because you saw several bowls of chips at the table and were too high to realize it was because there was a board game being played. You have been in jail for the past hour, but your main concern is trying not to zone out for too long on your grandpa’s ear hairs.
The Dagger: You are playing Clue and playing it wrong.