Best Classic Windows Version For Retro Gaming?

[Dreamcast Gamer]

For people interested in playing classic PC titles, selecting the right Windows version is very important.  Each new version of Windows omits some compatibility with older programs and increases support for newer ones.  It's fairly easy to find a cheap, working Windows XP machine and XP can run most Windows 95 and 98 games perfectly, but what if you're trying to run Windows 3.1 software or DOS games?  You might get lucky with a few programs, but most won't work. However, if you're using an older version like Windows 98, you'll be able to run nearly all of these, but if you also wanted to play games from the mid 2000s, chances are they'll refuse to load.

The truth is, there really is no best version of Windows for Retro Gaming, but there might be one that's perfect for your needs. The one I find myself using the most is Windows ME Millennium Edition. It certainly has its problems, but aside from one BSOD, I've never had any major issues with it. Except for a few Windows 2000/XP games such as Doom 3, everything I want it to run works perfectly. DOS support is limited since Microsoft tried their hardest to hide their command line OS as much as possible, but for my Retro Gaming needs, it's been wonderful. The best part is that it's very easy to configure like Windows XP and detected nearly all of my Hardware immediately. I was originally going to use 98SE, but I had too many compatibility issues with my PC so I switch to ME.

Which version of Windows do you prefer for running classic PC software and what era of games are you trying to run on it?

[TrekMD]

Windows 98 was pretty good.  It is a very stable version of Windows and many retro games work well.  XP is the other one.

[pinkabyss74]

FINALLY SOMEONE ELSE WHO LIKES WINDOWS ME!!

I think XP has too many troubles for old (1990s) games and emulators. ME is really good for retro gaming as it supports more RAM officially (1GB) and works pretty seamlessly with 98SE drivers, though it's best to find drivers and hardware that were properly written for ME because 98SE drivers might have small problems. Generic USB drivers for USB 1.x are useful too, which aren't in 98SE, though are portable.

The removal of real-mode DOS isn't that it removed, it was actually just hidden, if you have a WinME boot floppy it is possible to restore it IIRC at the cost of boot times slowed down.

[DeadVoivod]

I had a dedicated emulation PC which was running XP, and I never encountered any problems, was running smoothly. DOSBox was also just running fine.

[pinkabyss74]

I had a dedicated emulation PC which was running XP, and I never encountered any problems, was running smoothly. DOSBox was also just running fine.

There shouldn't be issues except with ancient emulators, most emulators work and existed in the XP era.
I referred to old DOS based software or 9x era.

[Dreamcast Gamer]

I've been testing out the gaming capabilities of Windows 2000 this week.  I haven't done much with it yet, but so far I am impressed.  It detected my Logitech controller immediately and I played some of Microsoft's PC titles such as Motocross Madness.  I still need to test 3.1 and DOS games, but I have a feeling they won't play any better than they do in XP which sometimes is quite well and other times means refusing to run.