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

Jacob Shelton
Updated May 20, 2024 156.2K views 10 items
Ranked By
5.5K votes
2.1K voters
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Vote up the classic Microsoft games that always kept you entertained.

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 10 minutes. Now that was living.

  • 1

    Pinball

    Pinball

    It was a revelation when computer users discovered they never had to go to an arcade again to play pinball. On one hand, the tactile nature of playing on big machines is unbeatable, but free games forever? YES PLEASE!

    848 votes
    The best?
  • Solitaire

    If you were born any time after 1985, you can probably count the number of times you've played Solitaire IRL on one hand. Who knew Microsoft struck anti-boredom gold when they included this classic rainy day game on all of their computers? 

    560 votes
    The best?
  • Minesweeper

    Do you remember how frustrating it was when you saw people solve Minesweeper in one move? Most of us were never able to capture that magic, but it must've been very, very satisfying.

    651 votes
    The best?
  • 4

    Microsoft Mahjong

    Microsoft Mahjong

    Admit it, you tried to play Mahjong so many times on Windows 98 and never got further than staring at the large pyramid of tiles, trying to figure out what to do with them.

    466 votes
    The best?
  • Chip's Challenge

    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. 

    506 votes
    The best?
  • SkiFree

    SkiFree probably offers the best gameplay to those who've never skied before. 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. 

    377 votes
    The best?
  • 7

    FreeCell

    FreeCell

    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

    358 votes
    The best?
  • Pipe Dream

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

    284 votes
    The best?
  • 9

    JezzBall

    JezzBall

    Oh JezzBall, you're just an out-of-date computer game, so you'll never know how happy you made a generation of bored latchkey kids.

    314 votes
    The best?
  • 10

    Rodent's Revenge

    Rodent's Revenge

    Rodent's Revenge was such a weird puzzle game, and it really doesn't get enough credit for being a kind of reverse Pac Man. Didn't the cats you trap turn into skeletons after the clock ran out? And isn't trapping cats kind of inherently weird? 

    304 votes
    The best?