Like Lord Reith, I first saw the word 'Bootleg' in this context in Tyler and Carr's Illustrated Record. I believe I bout this in 75 or so, when I was around 12 years old. I spent hours reading and re-reading that beast. And I read those strange album and song titles and wondered what they were.
The original edition of Illustrated Record had much more information on bootlegs than the later editions. But I had never heard or seen any., and presumed from their text that they were all dreadful.
A year or so later, an older friend gave me a bootleg catalogue from Pipé Records, a small record shop in Melbourne, Australia, that sold boots. It included tracklists and, from memory, some photos. And So many artists I had never heard of. I read that thing to death. I wish I still had it.
My friend then lent me some of his Stones boots. Jean-Clarke Mammorial Sonic Barbecue - which I loved. And then In Again, Out Again, and Out on Bail. Loved them all.
A few years later I saw my first bootleg in a market. Beatles, Live in Anytown, which I grabbed. Then a few months later, Omay Yad (Pink Floyd) for a few dollars.
Interesting aside, a couple of years later (early 80s) I rang Pipé Records, and chatted on the phone, They were really friendly, and then I asked if they had a copy of "In Again, Out Again", rather than asking if they had bootlegs. The guy's tone changed instantly. Never heard of it, he said, Don't know about it, Goodbye, and hung up.
Always wondered if they'd been busted.
GP