There’s a new invitation on False Machine to collectively share the oldest fragments of oldschool roleplaying that we still remember fondly, and just for once I’m actually aware of it while it’s still happening. So I can actually reply to it before everyone else has moved on from two weeks ago’s news.
As far as I can remember, the oldest oldschool roleplaying thing on the internet that I became aware of was Ben Robbins’ West Marches. That was something that even made a splash in the D&D 3rd Edition circles that I was exclusively frequenting back in those days. It was something people were aware of and talked about, and for me really was the first time I got any perspective on what D&D was like before Dragonlance paved the road to hell with good intentions. It was also the first time I encountered the idea that a campaign could be open world instead of following a fully written script that the GM had already at hand. But I think for the following couple of years, nothing much really came from this first encounter.
I think what might have actually started my initial interest in oldschool play might very well have been Chris Kutalik’s Pointcrawl. I might have linked to that post a dozen times now on this site since I started it in 2013. By that time I must have already been a frequent reader of RPG sites of this kind to consider making one of my own, and I think even more so than today, oldschool roleplaying completely dominated the environment. And in one of my first post, I did start trying to properly read the 1st Edition Dungeon Master’s Guide, which was regarded as scripture coming from the prophet’s hand himself. I bounced off that one pretty hard and still have no real love for AD&D myself. But Pointcrawl, that stuff was awesome! While West Marches had been a curiosity, Pointcrawling was something that really got me hooked. I think that’s really the thing that made me want to actually understand this whole oldschool roleplaying thing. When I first saw Spriggan’s Den appear in the link list of Hill Cantons, that was probably the biggest day for this site. I was being considered relevant by one of the revered sages. Of course, Hill Cantons is still in my link list and will remain there until the very end.
Other very important sites from that time were both Delta’s D&D Hotspot and Jeff’s Gameblog. Both are still very much alive and kicking with no signs of going anywhere, though I actually look at their new posts only very rarely these days, and they never were such a regular thing for me that I put them into my link list. I don’t remember any specific post, and I certainly am not going to try sieving through the archives, but it was something written by Delta that first made me appreciate the math and mechanics of the original D&D system. I think it was something about randomly generated monster encounters, which made me understand that those giant monster hordes are not just oversized battles against trivial critters, but actual seeds for entire spontaneous adventures. That was big for little old 3rd Edition GM me. Probably even more so than West Marches had before, appreciating Numbers Appearing was what really opened my eyes to a completely different way that games could be played and run.
I also want to shout out to Trollsmyth and Goblin Punch. With these two pages I can’t really point out any specific posts that stuck with me, but it was rather the particular styles of imaginations I encountered there. Both have played big parts in inspiring me to work on more creative and original material myself.
Getting somewhat off-topic from Patrick’s original question by climbing back up the stairs to the antechamber, but I really can not talk about my memories from the oldschool crypt without mentioning Joseph Manola’s Against the Wicked City! Joseph started his site at the same time as I gave the oldschool thing another try by looking into Basic/Expert for the first time, I seriously started with Sword & Sorcery worldbuilding, and I was finally starting to actually know what I was doing with the page and feeling like I had regular readers. So in a way, it felt to me that we were the two new guys entering the arena. And his Wicked City was a setting with very similar notions as my own, except that his was way better than mine. What was even cooler was that senpai notices me, and we frequently exchanged ideas in each other comments. And if you haven’t read his stuff, there’s some of the best gold on his site that is around. Your Demon Lord doesn’t need that many Hit Dice is certainly one of the gems that we have and The Long Haul continues to inspire my ideas for new campaigns just as much as Pointcrawl does to this day.
Also shout out to Justin Alexander. That man has always been unapologetically writing about 3rd and 5th edition, but he’s one of the OGs when it comes to teaching good gamemastering to us pipsqueaks and regardless of the editions he’s covering, I think I learned more about oldschool gamemastering from him than from anyone else. Calibrating your Expectations was where it all started for me, laying the foundation for my later appreciations for more down to Earth and small scale, grimy fantasy roleplaying.