The Ha! Ha! Guy originally appeared in the late 1800's to advertise Forbes' Insoluble Dry Plates, used in photography. (Fark Link) A Goodwill auction turned up a painting of a "Midland Man 1874" that looked eerily similar to the HA! HA! Guy. The back of the painting reads "The man who resigned a Midland position in 1874 and got his pay" A quick Internet search on Midland 1874 reveals that there was a Canadian railroad company, the Midland Railroad, that suffered severe financial troubles in 1874. Perhaps the HA! HA! Guy was a manager who pulled an 1874 Enron?