Wow, thanks! All of these comments will be very useful for my study. You have each brought up things that I did not intially think of. I frequent concerts where bands welcome “bootleggers” to their audience and it was at the back of my mind. Such a hippie-oriented culture (ahem, yes, I used the H-word) should embrace the modern-day form of bootlegging. I was aware of the OED definition, and now that I think back on it, I think that is where I initially got the idea of the “cowboy’s boot leg.” As far as I have found so far, this etymology seems to be the most logical. I also found in “The Cowboy Dictionary: The Chin Jaw Words of the American West, 2nd Edition” (Adams), that bootleg is also a mining term used to describe “a charge explosive that fails to break a rock.” How in the world did it get there? Applying it to the act of sneaking music around a concert venue seems to fit so much better. Along with that, I am also perplexed by the the numerous meanings and origins of just the word “boot” itself. It has origins in a variety of European languages, of which I am only slighlty familiar with the connections, where it was used as a verb meaning to “make better” or as a noun meaning “advantage or profit.” Now, this coincides so well with the moder-day definition of bootlegging, but it is a flase etymology. But how did the word so conveniently attatch itself to an article of clothing that can sneakily bring its wearer profit? No doubt, a boot makes life better, but is that false etymology also? Then there is the saying “to boot” which comes from the verb form, meaning “in addition to, besides,” but was the creator of “bootleg” so clever to have known this and made the connection in the seemingly literal term? Ugh. I hope I get this paper done by Tuesday.
Again, thanks for all of your help.