If enough of the same sound that the performer makes gets in from the monitor speakers, you start a feedback loop and that's when you hear the loud squelches and high pitched ear destroying screeches in speakers.
When you cup a microphone, you're essentially changing the pick up pattern and making it what's called omnidirectional. Since you have the cup at the back of mic, you get reflections of the performer and the sound gets pushed back into the mic instead of being rejected, easily creating a feedback loop. No good.