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    Monopoly Classic 
  • The Community Chest cards ever since 1935 have always had this gem in the deck.
    • What makes it even funnier is that is got nerfed to $10 in versions from 1936 onward. That's right, a Joke Item got nerfed.
    • Read that sentence again and compare it with Uncle Pennybag's image on the card. Him winning 2nd place of beauty will invite some Fridge Logic and some chuckles.
  • "Life insurance matures, Collect $100" Wait, that's not good!

    NES, SNES & Genesis 
  • 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.
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    CD-ROM 
  • In the 1995 PC game by Westwood Studios, each property is represented by a short animated FMV. When landed on for the first time, each one shows a vacant lot with a "For Sale" sign, with different versions for houses and hotels, as well as mortgages. Some of these are quite hilarious:
    • Mediterranean Avenue, the cheapest property in the game, is represented with what appears to be a garbage dump, with a spray-painted sign reading "4 sell". Compare to Boardwalk (the most expensive property), which is shown as a beautiful marble-walled field with a fountain, with its sign made of wrought-iron.
    • The orange properties are shown as iron-fenced grass fields, with pigeons and a metal "For Sale" sign on a thin post. For the third orange property to be landed on (whichever one it is), the pigeon will fly headfirst into the sign, pancaking itself.
    • The red properties are shown as picket-fenced fields with sunflowers and a cat. At the third one landed on, the cat jumps off the fence at a butterfly... only to somehow get flung backwards by a flower.
    • The green properties are shown as lovely, fenced fields with a pond in a mountainous area... with flamingoes walking through. At the third one to be landed on, one of the flamingoes actually tips over, revealing itself to be a plastic fake.
    • When landing on a property with houses or a hotel, you'll see them on the property... By which we mean, giant green plastic houses, or a giant red plastic hotel, randomly scattered around the lot. Occasionally, one of them will even be lying on its side.
  • Drawing the "beauty contest" card plays a Wolf Whistle.

    Nintendo Monopoly 
  • Waluigi takes the place of Mediterranean Avenue, the least profitable space in the entire game.

    Monopoly: Longest Game Ever 
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