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All 10 Old Microsoft Windows Games from the '90s, Ranked

Updated June 14, 2019 4.2k votes 1.4k voters 99.7k views10 items

It’s safe to say most of us grew up using a computer that ran some version of Microsoft’s classic home PC software, and because you probably weren’t a child accountant, you likely spent your time playing the games that came with Windows. Microsoft was very cool about including different types of games for all types of players. There were puzzle games, pinball, and even classic card games for those of us who enjoyed an old school sensibility with the added class of not having to touch a filthy stack of cards. But which were the best Microsoft Windows games? You’re going to help answer that question in this ranking of all the old Microsoft games.

Maybe this is rose-tinted hindsight speaking, but there was something pure about '90s Microsoft games. They all had a simple conceit, but never lost their luster. If you don’t think that’s true, think back to the countless games of solitaire you played and try to convince anyone you didn’t love it. Could you have been outside chasing butterflies? Probably, but then you never would have seen the fireworks that go off when you beat a game of FreeCell in less than ten minutes. Now that was living.

Vote on your favorite old Microsoft Windows games and if you were too cool for mahjong get real in the comments and tell us what you liked to play. 

  • Photo: Mircosoft

    For a lot of millennials Chip's Challenge was the first puzzle game you played, and it was the perfect primer to prepare your inner nerd for a lifetime of fawning over Legend of Zelda. Raise your hand if you still see that warp door in your dreams. 

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  • Photo: Microsoft

    SkiFree probably offers the best gameplay to those who've never skied before IRL. Thing is, once you've been out on the slopes, you know there's no way it compares to being chased by a pixelated abominable snow man. Thus, SkiFree has ruined your skiing forever. 

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  • 7

    FreeCell

    Photo: catsspat / flickr / CC-BY-NC 2.0

    Most of us will never understand how FreeCell is different from Solitaire, but moms of the world insist it's a totally disparate experience. Maybe it's something you only truly understand when you're over 40 and have a son who won't stop pretending to be a ninja and you're halfway through a bottle of red and, like, seriously, this game is not the same as Solitaire

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  • Do you think Pipe Dream is responsible for millions of millennials being unable to fix real world problems with straight forward solutions? What's not to love about this game? It's kinda like Tetris, but instead of clearing out lines of weird Russian blocks, you got to make a giant mess.  

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