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2.
"There is a real place called Hoople, in North Dakota, spiritually not too far removed from the real Deadwood in South Dakota, though the two places are at opposite corners of the states. Hoople, however, is a tiny place even today (population about 300) and can hardly have been significant enough in 1876—even if it existed then—to be the source of a deprecatory comment."

"According to Professor Jonathan Lighter’s Historical Dictionary of American Slang, it probably derives from Major Hoople, who was a character in a once-famous cartoon strip entitled Our Boarding House, which featured the goings-on at Martha Hoople’s rooming establishment. It was written and drawn by Gene Ahern and began to appear in September 1921..."

"...It would not have been possible for Al Swearengen (Deadwood) to have used the word in 1876, 40+ years before Gene Ahern invented the character (Major Hoople) and a hundred years before it was first recorded in print. The producer and head of the scriptwriting team (HBO: Deadwood), David Milch, has been reported as saying in essence that he picked something out of the air to serve as a suitable insult without great concern for its etymology. It seems he must have heard it somewhere and it came conveniently back to mind while writing the scripts. It’s definitely an anachronism."
"Those damn writers on Deadwood don't research their slang words, but that doesn't stop Grandma from calling everyone a 'hoople head' anyways."
by The Chanel August 30, 2006
 
1.
a member of the ignorant masses; an uneducated commoner; an idiot. word popularized by HBO's Deadwood
Try not to use big words-- it confuses the hoopleheads.
by liberalicious August 24, 2005
 
3.
(Origin - unknown) n. - Hoople-head is probably derived from the word hoople, which means hobo or buffoon. See the 1960s novel by Willard Manus entitled, "Mott the Hoople".
As used in Deadwood, an HBO original series, "...bunch of f#$%ing hoople heads."
by Ken Serrine March 31, 2005
 
4.
I just spoke with my Uncle who is almost 90 years old. He said he recalls the word of Hoop Head being used when he was a young man. It's meaning was a "Drug Addict", could this be what Al is referring to since there is a lot of drug use on the show?
"Don't give those hoople heads any more drinks."
by Lanette May 05, 2008
 
5.
dervied from slang "hoople" which means a drunk; a drunkard

Source: HBO Original Series Deadwood
Give those hoople heads some drinks to calm them down.
by laura andora July 08, 2005
 
6.
1 It derives from Hoople North Dakota.
Simple isn't it.
2 One other common 1800's use was also because of the hoop on a miners head, they used lights on hoops to go in shafts.
Hoople head did not derive from Deadwood the TV show, lol.
by Chef Didier May 06, 2008
 
7.
I agree this term came from "Deadwood", but I don't think it means drunk or drunkard specifically. I think a more accurate definition would be clueless bastard or loser or lowlife, or particularly a combination of these.
In the show, these people often tend to be drunk or drinking, but not always.
Go buy the hoople heads a round of drinks.
Go get those hoople heads out of the street, before they get run over.
by Mr. Jan March 26, 2008