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I just remembered Win98 and Win2k "Restart in MS-DOS mode". I used to use that all the time in the late 90s rather than fiddling with DOS games to get windows compatibility.
At some point, I selected that reboot option for the last time... Single tear rolls down my cheek
A nice trip down memory lane.
I disagree about Windows XP being a transformative shift, though. Many gamers ran Windows 2000 for its reduced system overhead, plus you still had the relative stability of the NT kernel. I didn't switch to XP until several years later, and iirc it was because they cut support for something on Win2k.
It's also ironic that they say it offers a "compatibility" that didn't exist before. Windows 98 with MS DOS under the hood was fully compatible with older games, and it was only with the Windows XP, 2000 & NT line when this compatibility was broken and those same old games no longer worked out of the box. The only way to get some level of compatibility back was to introduce workarounds and special "modes" that they had to add to XP which often didn't really help if your DOS game was old enough.
Imho, getting rid of the underlying "command prompt" might have been a good thing for the more casual gamers, or the ones who were new in the hobby... but most gamers coming from MS DOS at the time were not afraid of COMMAND.COM, many of us only moved from Windows 9x when we were forced to (due to newer software no longer working, or having to change PC). To me, the newer editions always felt more opaque.. giving less control for the sake of security. It was getting harder and harder to try to understand what your OS was doing. With Windows XP you no longer had an AUTOEXEC.BAT or a CONFIG.SYS for power-users to customize.