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We are currently working on additional community features, such as submitting your own games and voting on which suggestions work...and which don't. Thank you for visiting and pardon the dust while we grow to better serve you.
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Pre-Windows 95 Games
Most games released prior to Windows 95 ran either in DOS or Windows 3.x.
On Vista, DOS compatibility for games is significantly reduced from what it was in Windows XP. In Vista 32-bit, most DOS games simply will not run and in Vista 64-bit, DOS applications will not run at all.
For Windows 3.x applications, it's a similar story. On Vista 32-bit, most games will work, but on Vista 64-bit, you're out of luck.
Fortunately, there are options.
DOS Games
For DOS Games, we recommend that you try using DOSBox. DOSBox is a DOS machine emulator. While it isn't perfect, it's good enough for 99% of the DOS games that are worth playing. It works with both 32-bit and 64-bit flavors of Vista.
Windows 3.x Games
(Note: These solutions assume that you have a legitimate license for Windows 98 Second Edition lying around your house.)
Windows 98 Second Edition had great Windows 3.x compatibility, and if you own Vista Business, Vista Enterprise or Vista Ultimate, Microsoft has your back and has made Microsoft Virtual PC 2007 available as a free download for those operating systems.
Microsoft Virtual PC creates a full emulated PC that runs inside of your machine. For instructions on how to install various operating systems inside Virtual PC, including Windows 98 Second Edition, check out "The Virtual PC Guy's WebLog."