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It's also worth mentioning that the DOS -> Win 95 era had some ridiculously bad coding practices that were fairly common. Things like programmes attempting to allocate all available memory. Things that you couldn't actually do in Win NT.
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Or the original Sim City, which allocated some memory, freed it, then tried to use it later. It worked fine in DOS because there was no multitasking, so no other program could attempt to use that memory. When the first versions of Windows first came out, everyone started complaining that it was killing their programs and blamed Microsoft rather than the original developers' poor coding practices.
Microsoft actually wrote tests in to Windows to see whether certain programs were running and then allowed illegal behaviours based on the results. For instance, every time you open any application in any version of Windows right up to WinXP, the OS is testing to see whether you're playing Sim City. One of the reasons why Vista is actually a more efficient OS, but that certain programs died a lot, is that they got rid of all that automatic compatibility bloat.