I was enjoying an episode of "Seinfeld" last night, the one where a loopy friend of Kramer's illegally videotapes movies (direct from the screen in the cinema) and then sells copies on the street.
What is the origin of the term "bootleg"?

This is from World Wide Words (link below)

BOOTLEG

From Jeff Martin: "How did bootleg come to mean something of illegal manufacture?"

It's a surprisingly late coinage, first being recorded from Omaha, Nebraska in 1889 (with the related bootlegger being recorded in Oklahoma the same year). Prohibition gave it a huge boost, of course.
Bootleg was at first a literal term. In the days when horsemen wore long boots, their bootlegs were good places to hide things. For example, this description comes from The War in Kansas by G Douglas Brewerton of 1856: "He sports a sky-blue blanket overcoat (a favorite color in Missouri), from the side-pocket of which the butt of a six-shooter peeps threateningly out, and if you will take a look into his right bootleg, we should say that a serviceable bowie-knife might be found inserted between the leather and his tucked-in Kentucky jean pantaloons".
By an obvious-enough figurative extension, illicit goods that had to be kept hidden were referred to as bootleg commodities. The word seems to have been applied specifically to alcohol at first (again, Prohibition helped that association greatly), though more recently its application has broadened to encompass a whole range of other illicit or pirated goods.

World Wide Words is copyright © Michael Quinion, 1996-. All rights reserved.


http://www.quinion.com/words/qa/qa-boo1.htm

From "The Story of English" McCrum,Cran and MacNeill p.242
"At the fontier itself, whiskey was traded unmixed,and often used to corrupt the local
Indians. Congress tried to regulate the worst excesses of the liquour tradebut the pioneers
tuned to bootlegging (the whiskey would be sold illegally to the Indians in a flat
bottle that could literally be carried in the leg of a boot). Bootleg in the sense of an
unauthorized sale, has now become part of the language wkith phrases like "the bootleg album."

H.L. Mencken wrote: "I proposed the use of bootician to designate a high-toned big-city bootlegger in the American Mercury, April, 1925.. The term met a crying need, and had considerable success. In March, 1927, the San Jose Mercury-Herald said: 'Our bootleggers are now calling themselves booticians. It seems that bootlegger has some trace of odium about it, while bootician has none.'"

I guess bootician must have gone the way of Prohibition.

well, not quite (my apologies to teD):

Q. Why did the ugly ghost cross the road?
A. To visit the bootician.

Q. How does a bootician style a ghost's hair?
A. With a scare-dryer.