bootlegging and piracy is nothing new, whenever there is something people want when they don't have the funds to afford it (seriously, who the hell is gonna drop $12 for a cd that has 15 songs, and of those 15 songs there's probably only gonna be like 3-5 that you'll actually like).. and seriously, iTunes is a joke, i have over 15K songs between my 2 iPods, does apple really think i will spend $15,000 on music? if they do, they must be high off their ass on some really, REALLY good weed (then again, for iTunes to be this popular, there must be millions of people out there dumb enough to actually buy songs so who knows)
as rob stated, bootlegging was around when cassette's were big, and it was definitely big before that. the only difference with it now is how easy it is to do it
before, piracy was similar to drugs, you had to know a guy who know's a guy to get what you want
now, all you have to do know how to use basic functions of a computer and boom, you got music
no matter what the format will be, people will find a way to bootleg it