A sound engineer friend said Chris Isaak had that IEM popped out of his ear so he could hear the stage ambiance. My friend is probably right, but seems odd that the performer would do that on a televised event.
Having never used a custom IEM, I'm having to guess what the experience is like. Is it because the mix is not great, or simply because no amount of good mixing can make up for not directly hearing your own voice when singing?
Not really sure not being a vocalist myself but I think it has to do with the difference in sound of what your hear resonating in your head versus what comes through from the mic.
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