This topic has become near and dear to my heart over the past three years. Thanks to the magic of BitTorrent and archive.org, I've built a ridiculous collection of live music recordings. (How many? Thousands. At least five. Compulsive collectors should not be allowed Internet access.)
This book by Clinton Heylin is a fascinating look at the bootleg* industry (it also touches on free tape trading, which is analogous to today's BitTorrent community). The author focuses on rock and roll bootlegs, both studio and live recordings. The first section of the book, my favorite, tells about the vinyl bootleggers of the 1970s and 1980s. There are some hilarious stories, and Heylin reproduces some of the classic cover art. The second section covers the early CD era up to 1994. Much of this section is devoted to copyright law issues, and when things get complicated the narrative drags a bit. In the brief third section, artists such as Lenny Kaye and Graham Nash talk about the importance of bootleggers preserving performances.
This is a great book because no other author has addressed the rock bootleg industry in such depth. It does have some weaknesses, though. Each chapter begins with a 15 cm2 photo of a bootleg cover, but all of the other bootleg covers are restricted to the margins. Those photos are a disappointingly minuscule 4 cm2. I also would have preferred more bootleg stories instead of the lengthy distinctions about copyright law. Finally, be aware that this is by no means a guide to bootleg recordings. Only a few significant releases are discussed with any detail. All the same, anyone interested in rock and roll history should find plenty worth reading in Bootleg.
Note: I read the hardcover edition of the first book below. Although the second has a different title, it is merely an updated edition of the first. Without reading it, I assume Heylin blames stronger copyright laws and online file sharing for the "fall" of the industry.
Current tally: 66 books finished, 61 books acquired
* Note that true "bootleg" records and CDs contain material that has not been commercially released through official channels. Bootlegs are not the same as "pirate" recordings, which are merely counterfeit copies of official releases.