I’m sticking to Windows 95.
I kept around an old machine that ran Windows 98 because I really enjoyed some of the old programs. Unfortunately the media playback technology became so ancient that it no longer became viable for anything except software of that vintage. Plus the machine took forever to boot up, sort of like waiting for the picture tube to come on back in the 50s and 60s. Windows 7 will someday be a dinosaur but I'm not sure the technology is going to progress much further than it already has.
But make sure you have installed WINDOWS 95 SYSTEM UPDATES !