I have to say there were two funny costumes we made for my brother.
One Halloween my mother dressed me up as Sylvester (stuffed newspaper in the tail so it was stiff and swayed when I walked) and my brother as Tweetie Bird. My brother at that age and this round face and big blue eyes so Tweetie was perfect.
The most hilarious one was when my mother dressed him up as a woman. My mother was fairly heavy at the time and she took one of her dresses. She then stuffed a pillow in the front for breasts and pillows in the back for the butt. He was as wide as he was tall practically. She put a wig and hat on him, and some gloves and a purse and sent him on his way.
I about died laughing when he was walking with his fake butt bouncing up and down. He really looked like a fat little old lady waddling down the street. I think he was around 12 at the time LOL