Funny / MONOPOLY

Monopoly Classic

• The Community Chest cards from 1935 to 2021 always had this gem in the deck.
  You have won Second Prize in a beauty contest! Collect $11.
  • 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.
  • Landing on Income Tax after passing Go. You hear the fanfare after you pass Go, followed immediately by the change in music and the sight of your money going into the Capitol.
• 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, brushing himself off, and storming off indignantly. It looks more like he's being ejected from some high-class party than getting out of Jail.
• 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.

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

• The fact this version of Monopoly exists is itself hilarious. Monopoly for years has been infamous for taking a long time to play. So what does Hasbro do? Make it longer. There are now 66 properties available and you only get one die. You can force someone to sell you a property they own by paying $10 more than the rent you owe. And the only way to win is by collecting every single property. The overall reaction to this edition was about what you would expect.