Monopoly (Windows, 1995) All-AI Gameplay -

Monopoly (Windows, 1995) All-AI Gameplay

Mr. Eight-Three-One
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There are a million ways to play this game, and it somehow still can’t be made good.

That’s right, it’s Westwood’s 1995 computer game adaptation of the (in)famous board game. Just for the record, that one-liner was a quip about the base game — this computer game is actually a very valiant effort and sometimes considered the best adaptation due to its personality and heavy level of customizability. That said, if you ask any board game enthusiast worth their salt about what their opinion is on this game, it’s probably not a very flattering one. Not that I can blame them — it was deliberately designed to be bad from the outset (after all, it is about the dangers of unchecked capitalism, not that anyone ever noticed).

So as the title implies, this was a purely AI-controlled game, I did absolutely none of the work. Figured it was a better use of my own time considering games can drag on and on, so I wanted to just let the computer have at it. In retrospect, I think turning off the “thinking” time may have been a bad idea because it means things like trades happen way too quickly for the human to notice, but eh, it’s a small price to pay. If I ever do another Monopoly PC adaptation though I may not be so lucky. Also, I love how the AI names are based on already-existing video game characters.

I have very little to say about this since I didn’t do any of the playing. Like I said, it’s a really good adaptation that has a lot of neat little touches, and while I may not like the board game it’s based on, I think Westwood did a great job with what they were given and I do hope you enjoy the video!


  1. 43:50 43:51 I've always liked the song Railroad Ode in Westwood Monopoly. I would say its the best track in the game.

  2. This is probably the most I've ever seen people land on Marvin Gardens…

  3. Computer may cheat? Never seen that as an option in a monopoly game before 😂

  4. My mom and I used to play a 1996 Monopoly Junior amusement park board game when I was a little boy. I also had a 2007 Monopoly Disney/Pixar edition board game when it first came out. Both of them were fantastic! I believe I still have them. Although I never had Monopoly video games back then, watching footage of this one brings back memories, so I should consider purchasing this game on Amazon or eBay one day. Wonderful video!

  5. I was playing Monopoly with some friends a few nights ago and both times I was a ship. Coincidence? I think not!

  6. This is the old and classic Monopoly. I liked the NES version

  7. I love how in some of the status images, the houses are just carelessly plopped all over the place, sometimes on top of each other like the example seen here.

  8. Picking the dog token for the AI named Guybrush? I see what you did there!

  9. I actually like this version of the game. I bought it about 3 or 4 years ago, and it's great. Like the cash register ding when you collect money (i.e. collecting $200 for passing GO at 15:35 and 17:15, or $400 for landing ON it at 17:35; house rule).

  10. I grew up on this game. It was amazing! As a kid, we used to make fun of each other on "Receive for Services" because of the greedy minister, when our father was anything but greedy. Beauty contest: that card gave us good laughs! Bank dividend: We used to make fun of each other for "smoking." In fact, the NES version of this game censored out the smoking to make it more "kid friendly." Today, the original designs have been replaced with more durable cards, but with more boring look to them.

  11. As for this, it has the Parker Brothers logo plastering the Hasbro Electronic Entertainment logo as well, but the Westwood Studios logo is still intact as well.

  12. Plus, the best thing about THIS Monopoly game is the soundtrack. You can't make a better Monopoly soundtrack than this one. It's DA BOMB!

  13. That tinny piano sound from the old Soundblaster MIDI synthesis brings back memories.

  14. The music sounds like Sega Genesis styled music.

  15. Poor Guybrush couldn't get a break. Had almost all properties but kept landing on the few properties owned by Fox. He shouldn't have sold his orange to Fox earlier because he would have been the only player with the ability to buy houses.

  16. 45:30
    Ouch! Poor Dana! But at least the "bankrupt" animation and music works here.

  17. Fdg SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey SwiftKey e e e e e e SwiftKey

  18. Everyone here so far who ran the Monopoly CD ROM program has been unaware that you can custom-name AI players.
    For example:
    Four "Fox" AIs (Fox, Falco, Slippy, Krystal)
    Or two "Kitana" AIs (Cynder and Kalderra) with two "Tarbosh" AIs (Spyro and Erek)
    Or six "Simple" AIs (Clank, Kit, Alpha 5, Data, Tron, and XR)

  19. If you played this exact game, but with NO TRADES, how many moves do you think it'd take to get a winner?

  20. GUYBRUSH! Where did they get these names? I used to create 5 players against 1 AI then transfer the other players funds to my account so I could whoop the AI.

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