1guy1cup Share definition Flag a video in which a man sticks a cup up his butt and then it breaks, causing bleeding. The name is a spoof on 2girls1cup. "dude, have u seen 1guy1cup?" "yea, im definitely straight now" 1guy1cup by narstytoanexremedegree January 1, 2009 0 0 Get merch Get the 1guy1cup mug. Buy Now — $32.95 See more merch