I don't use classic cups, so I don't tend to use that move, but I do use the move where you pretend to jam your wand through the bottom of one cup. My routine is mostly a comedy routine, and I do this quickly in one of the early phases of the routine to get a quick laugh mostly.
It's only as funny as you make it. I've found having obvious and/or terrible early phases is a great way to get people off guard for when you start pulling out oranges or crystal balls or whatever you're using for loads at the end of the routine.