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If you use Win9X, you will need one.
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Just to clarify: digital playback through the IDE cable is hardware dependant, not OS dependant. It will work in Win9X if your CD-ROM/DVD device supports DAE. It works the same way as ripping a CD except that it streams the data to the inputs of the soundcard rather than saving it to disk.
The benefit is that the digital signal is converted to analog by the soundcards DAC, not by the (usually cheap and crappy) DAC in the CD-ROM/DVD device, resulting in better sound.