In 2018 I became very frustrated with how little gaming i was getting in at game-time. D&D5e and SR5 are just too slow and too fiddly for my needs. Between the wife's 60-hour work weeks and the kids, sitting down together on Firday nights for a 3-hour game just wasn't cutting it. We often got only one or two encounters done a night, and maybe four total over a week.
I wanted more game in my gametime. I missed how fast you could play D&D when I was a kid. I started looking into lighter and faster TRPG options to fill our time. I had been vaguely aware of the OSR existing, but this was the first time I really decided to look into it. With G+ gone, however, I had missed the boat on the easy way to get into the OSR.
I quickly found YouTube had a handful of reviewers and philosophers who really broke it down well. Ben Milton of Questing Beast, Professor Dungeon Master of Dungeoncraft, and Hankerin Ferinale from Drunkards & Dragons (now RUNEHAMMER), all served as a great gateway into the weird and wonderous culture that had grown up around the OSR.
The OSR had taken the wildest and weirdest elements of D&D play and cranked it up to 11. We had the appearance of what we now loosely call "Gonzo" gaming after the term Hunter S. Thomson used to describe his wild, subjective, drug-injected, often hallucinatory-feeling journalsim.
Gonzo takes a number of different forms, and Venger Satanis and Aaron the Pedantic devoted a whole regular livstream, "Gonzo Up Your Ass" to trying to give it a clear definition, without coming to a final concluson as to what exactly it was.
OSR modules, settings, and resources favor a much darker, stranger, wilder, and weird setting than D&D had dared to put forward in its early days.
OSE's adventures like A Hole in the Oak, The Crystalline Grottoes, and Holy Mountain Shaker combine the mythic with the absolutely absurd. Man-eating tree-babies, goat-man tea parties, and slumbering fish gods paint a world in shades of Alice in Wonderland.
Dungeon Crawl Classics offers wild, off-the wall adventures in every module. Cosmic titans, resurrected chaos lords, legions of immortal mutated paladins, jealous frog gods, and bizarre ancienr evils suffuse their modulues. Even their most conventional dungeons are twisted into something comic bookish, pulpy, and weird.
Lamentations of the Flame Princess often offers adventures where level is irrelevant and combat avoidable (and leathal). In these adventures the bizarre, monstrous, surreal, and lovecraftian are painted Jackson Pollock-syle across early modern europe. Adventures feel like a mix of a bad mushroom trip and H.P. Lovecraft.
Where LotFP produces more conventional fantasy, it is rife with body horror, weird chaotic magic, and black humor. Often ending in a bloody screw job.
Strange fantasy that sprawls across different cultures and eras than late medeival europe is definitely one of my facourite hallmarks of the OSR.
As is the way some books and games like Ultraviolet Grasslands and the Black City take gaming experiences from other hobbies and turn them into something new and strange for classi TTRPGs.
Other massive dungeons like Barrowmaze, Highfell, and Rappan Athuk take the venerable D&D dungeon crawl and try to add enough strange and deadly complications and light-hearted odities to make them ore of a functional parody of D&D as it is an homage of the classic design.
Weirder, harder, pulpier, funnier, higher stakes, more risque... The prominent creations of the OSR have always been interested in taking the vanilla TSR D&D expeirience - and the expeirence of Advanced Fighting Fantasy, Warhammer Fantasy, Star Frontirers, Gamma World, and a few other great classics, and pushing them beyond the safe limits of what a large corporation dared to create 30-50 years ago. These creations celebrate just how far you can take your imagination in these games if you look past what was originally offered in Greyhawk or Mystara.
I think this has been overlooked in recent attempts to define the OSR I have seen online.. There is more there than an attempt to reacpture old styles of play; more than creating a new way to play old adventures; more than a design philosophy; there is a common impulse for exploring the outer limits of the medium, and a common aeasthetic language that I think often gets overlooked.
We are all trying to take some of those old and simple rules, and get something more out of them.