There is, of course, no singular event that one can point to and say, “The OSR started here.” Certainly it was a product of a particular time within the gaming hobby, wherein a number of circumstances combined to make the OSR possible. D&D 3.5 was petering out and 4th edition was received to blasé reviews or outright hostility. The OGL allowed games such as Castles & Crusades (2004) and OSRIC (2006), and later Labyrinth Lord, Swords & Wizardry, MicroliteXX, etc. to come about, and desktop publishing and the increasingly sophisticated abilities of on-demand publishing made it possible for individuals or a handful of people to put out really incredible products for little or no cash up front.
2008 was the year many flagship OSR blogs were founded, such as the Retroroleplaying Blog (founded February 20008); Grognardia (March 2008); The Society of Pole, Torch, and Rope (August 2008); and Bat in the Attic (October 2008); among many, many others too numerous to name. These blogs and message boards such as Dragonsfoot and the Knights and Knaves Alehouse (again, plus many others) fostered a community of deep introspection, analysis, and discussion about just what made older games great, on a mechanical, “player ethos”, and aesthetic level.
However, one thing I've noticed in the last year or so is that the level of philosophical analysis has decreased dramatically both on the blogs and message boards, in favor of an enormous wave of practical application. There are far fewer fundamental questions being discussed and older editions of D&D being evaluated, and many more reviews of new products, analysis of older non-D&D games, organization of face-to-face and virtual events, and the like. This, I think, is the transition between the first phase of the OSR to the second.
That’s not to say, obviously, that nothing of practical use has come out of the OSR in the last four or five years; far from it. But while the first phase of the OSR has seen foundational works such as those mentioned above, what we are now seeing in the OSR is a flowering of material that take off in wild new directions. Now that the final holes in the retro-clone coverage have been filled (the basic game-play of (A)D&D 0E, 1E, and now 2E are covered by multiple products), the OSR as a whole seems self-confident enough to break off in new directions.
We see this with games such as Lamentations of the Flame Princess (2010) that take the D&D game into new directions, but also with “reconstructions” of games that never saw print, such as Dragons at Dawn (2010) which attempts to recreate the game as it was played at Dave Arneson’s table in the very earliest days of the hobby, or my own Adventures Dark and Deep (2013) which attempts to show what direction the game might have taken if Gygax had stayed with TSR in 1985. There are fantasy games that are not based on the D&D rules, but harken to the old-school “feel” such as Astonishing Swordsmen & Sorcerers of Hyperborea, The Secret Fire, and Adventurer Conquerer King. We see science fiction games such as Sorcery and Super Science! and Stars Without Number. There are innovative and envelope-pushing settings and adventures such as Carcosa and Vornheim. And more material is being published every day.
Now, of course, we live in a hobby/industry where Wizards of the Coast has seemingly embraced older products in their back catalog, making them available in pdf format or in distribution-chain reprints. Old TSR stalwarts are publishing new and exciting material with their many decades of experience to guide them. So the landscape is once more changing. But in that change I see really good times ahead. The OSR has done its soul-searching, we've figured out what we are and what we like, and we’re settling down to the business of doing it. “Mainstream” gaming has caught up to us, and for a short while at least, we’re driving the bus. Let’s not hesitate to be bold and confident, and take things in exciting new directions.
As Gary Gygax said, “One more thing: don’t spend too much time merely reading. The best part of this work is the play, so play and enjoy!”