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- The Community Chest cards ever since 1936 has always had this gem in the deck.You have won second prize in a beauty contest! Collect $11.
- "Life assurance matures, Collect $100" Wait, that's not good!
- The scene for going Bankrupt is Pennybags in a dark alley pulling a fish skeleton out of the trash can.
- The music when you land on Income Tax or Luxury Tax, followed by the Capitol Building (instead of a cash register) eating your money.
- Everything about getting out of Jail, from the low 8-bit voice bellowing "Don't be coming back now" to Pennybags literally being thrown out on the street and walking off to a series of buzzes and beeps.
- Whenever a CPU player tries to get the remaining property for a monopoly from another CPU player by trading, only for the second player to immediately say "NO" without even considering an offer. Even funnier is if the monopoly is a two-property one (the purple group, the blue group or the utilities) and the second player then tries the exact same thing, to the exact same reaction from the first player.
- Waluigi takes the place of Mediterranean Avenue, the least profitable space in the entire game.