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?
'Midland 1874' may also refer to a series of locomotives manufactured in England, a strip of track laid in the Western part of the United States, or possibly an Illinois railroad company that foreclosed that year.
The HA! HA! Guy is the Midland Man reincarnate.