I come to the OSR from a different angle; I always wanted to check out D&D or similar as a kid, but it never really happened. I had some friends that were into Vampire, but they did LARPing and for a teen who was very very insecure and concerned with hiding their inner dorkiness, I never took the plunge. My first exposure to D&D was looking through a bandmate’s AD&D 2E material, but I didn’t really play until well into adulthood when I played Pathfinder and then later 5E. I ran 5E a few times as well, after getting some feedback that I’d probably make a good DM. I think I’ve done a good job running 5E, but I didn’t really enjoy it. Or rather, there was a lot about it I did enjoy that felt undermined by things like running combat or setting difficulty classes and keep tracking of too many numbers. It felt like it was beyond the limit of my cognitive load. I was cognitively encumbered! Further, the kinds of stories we were telling weren’t that interesting to me. I kept wanting to make things weirder, and more difficult, and for some reason it felt like doing so was causing tension with the other mechanics. I didn’t want combat to always be the only option, and felt it should only very rarely be the best option. But D&D, for better and worse, is pretty much built entirely around combat.
I still enjoy 5E as a player in my friend’s ongoing campaign, but I realized running it just wasn’t for me.
Around the same time I discovered Dungeon World, which seemed to be ticking all my boxes. The focus on the fiction and narrative complications over binary skill checks was revelatory for me, and the idea that the moves on the playbook weren’t a menu of options but mechanics that may or may not get triggered opened things up; in 5E it often feels like you can only do stuff that correlates to your skills. In DW it felt like you could do anything.
And then I started exploring the various hacks of DW, and started to learn more about the OSR. The personalities and the seeming dogma of OSR as a community turned me off (since often it’s the loudest, most awful voices that are easiest to encounter) but checking out some of the various retro-clones, I knew this kind of play was more what I was looking for. Some of the particulars of some of them went over my head or past me, since I never played OD&D or b/x or whatever else, and it did feel obvious that some mechanics were only in there for purely nostalgic reasons. I still felt I was more into the narrative focus of DW, but there was no doubt these games seemed better geared to play around with the kind of gonzo nonsense that seemed most fun to me.
And then I happened into a playtest of @jasonlutes’ Freebooters on the Frontier 2E, which felt like it marries some of the best stuff from DW with the best stuff from the OSR. And while the playtest kind of fell through, I decided to run my own game, and seven months in, it’s been an incredible experience. Early on, one of the players reported back that “it feels like my level one character just happened into a high level campaign, and it’s awesome.” It was pretty much the best compliment ever.
So for me, it’s not about nostalgia, because I can’t be nostalgic for something I’ve never experienced. “My OSR” is about plunderers, in over their heads, traversing the dangerous wilderness in search of riches, being hopelessly outmatched at every turn. It’s dangerous, it’s weird, it’s got some creeping cosmic horror, and the fun comes not from being superheroes saving the world, but from surviving and forming community in a world that’s brutal and uncaring. And occasionally being heroes and getting involved in political conspiracies where they’re maybe even more in over their heads than when exploring dungeons and fighting monstrosities.
Still love cyberpunk. If you are looking for the DW of Cyberpunk, I can recommend The Sprawl. Veil 2020 is more WoDu of Cyberpunk 