It's when you know something about someone else that sets them off and you bring it up in conversation...you are "cranking the monkey"...kinda like an organ grinder cranks the organ...except you are cranking the monkey instead! It's usually a sore spot with them...something that happened or didn't happened that they are mad about. It's like reopening the "wound". It could also be just a reference to something about them (cosmetic or otherwise) that they are not happy hearing.
I love it when you wear your baseball cap backwards...it's so "mature" looking! Oh...I didn't mean to crank the monkey?
by Mike Piskulic September 14, 2006