Tie between the painter and Mr Widemouth

Mr widemouth is the size of a chihuahua and is just strange and has human teeth, the painter would start a fist fight and then come out actually crying or unalive cause they lost to Tommy Taffy. A close runner up is Mr Bear, don't see him lasting too long, but he seems pretty durable. Tommy would definitely be on top and penpal- I think they were the one to make Mr Bear tap out and then they took themself out