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I'm weird when it comes to that. It feels awkward to my sense of hearing to play music from another source while playing a game. If I'm doing something on my computer, for example, and I have a portable stereo playing music, something about that bothers me and I'd rather be listening to it through my PC speakers.

Same thing with consoles. I'd rather a game have custom soundtracks than have a sound system playing music separately.

Then to top it off, there's also the balancing act of making sure the volume of the music is just right and not too quiet or too loud.