A brief conversation to enhance this thread happened, is there any operating system besides Windows 98 Second Edition that has a switch for automatic digital audio redistribution on the setup menu? Such as ArcaOS?

From the audio control panel, the switch is "DAE" digital audio extraction. Different terminology, same concept.

The end functionality is to be able to randomly play any song off a music CD while playing a game. I've done this with Windows 98 SE and Carmageddon II. Anyone else have success?