it doesn't matter the size or the exact shape, just make it really, really fast
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It looks like a hourglass
If by "glass" you mean the hourglass from Phantom Hourglass, you can't draw an actual hourglass, you need to draw an Arabic numeral eight. (like this: 8) If you draw the figure with one circle on top of a smaller circle, it won't work.
You could draw a quarter.
Draw it yourself or use a tutorial on YouTube
Well if you want to know its simple just go to "How to draw Mario" (Google it if you can)