If you can find some sort of freeware equalizer that might help a bit. Only equalizers I've used have been program/codec specific (AC3Filter, iTunes), or part of my audio drivers/related software suite. So unfortunately I can't name any off the top of my head.

Have you tried other headphones in this computer before? Were they this quiet?

Hmm....

Shouldn't your half-deaf friend be doing everything in his power to keep what's left of his hearing? If I were him, I wouldn't be listening to loud music.

Unless of course it's Metal. Going deaf listening to Metal is honorable. Going deaf listening to anything else is stupid.

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I don't know. I figured he would want to do that, but I guess he's more of a enjoy-it-while-you-can type of guy. He's had so many operations and what not that he can barely hear you speak normally, so to hear anything, he has to crank up the sound pretty badly. It's more necessity than anything else at this point.