2 of my boys did very funny shtick. When my youngest was in 9th grade in YFR, he dressed up in TAG high uniform, borrowed his aunt’s sheitel which he wore in pigtails, put on rollerblades and took shelach manos to his RY. He handed him the package and then gave him a big smooch. The Rosh nearly fainted and he said “Rebbe take it easy, don’t you know its just me?”
My other son must have been 19 or 20 and was very, very skinny. He bought himself a costume and wouldn’t tell anyone what it was. Purim morning he comes down the steps in this huge blow up sumo wrestler costume that was hysterical. He could barely walk. Everyone was doing belly bumps with him.