I guess I am dating myself here. I remember when the internet first started coming into popularity and mainstream towards the mid/late 90s. Around 1997 or 1998 I began surfing the net, albeit for limited periods of time, and came across a few NES fansites, including two of the big names from that time, NES World and tsr's NES Archives. At that time I then began reading all of the information about the games, and there was a ton of weird stuff on those sites. Learnt about Mario IV and 14 then, Somari, the Paneasians, and all kinds of other amazing games. Some of the aforementioned stuff was unlicensed, others were just plain pirates, but I immediately became hooked and tried to do as much research as I could into that stuff.
My first unlicensed game cart was probably either Captain Comic or Silent Assault for the NES; and I remember a few months later searching the used bins at Babbages (anyone remember them?) and walking out with F15 City Wars, Tiles of Fate, Dudes with Attitude, and Venice Beach Volleyball, the latter 3 were boxed. Good times and good memories. And from there I just built a knowledge and a nice collection of games over the years, via trading, and the like.
As for my first *true* pirate game (not unlicensed), I believe it was a generic Supervision 72 pin multicart, 350 or 360 games in one, something like that. I had paid about $10 - $20 for it at the time, and although the games were mostly just common multicart fare, I remember being really tickled with that purchase.
I remember later when a Russian friend would hook me up with some really cool Famicom bootleg stuff from that region, and of course how could I forget getting a set of new old stock Sachen games back in the day. It was only a few titles, as that was all I could afford, but I was just happy with having that. For a high schooler without a job most of the time, I had a damn fine collection of games back then, if not even better than my collection today. All it took was sweat, blood, tears, time, and dedication --- traits which many seem to lack these days.
Wow, the memories. Those sure were different times.