To better understand the origin of OSR blogging a while back I did some archive snooping to see how Jeff Rients and James Maliszewski (of Jeff's Gameblog and Grognardia, respectively) originally got into writing about old school gaming.
It turns out that Grognardia grew out of a LiveJournal blog called "The Schizonomicon: Musings of a Sleep Deprived Dad". Maliszewski started writing this blog in 2002 and it was initially filled with posts about very personal non-gaming issues. Starting around 2006 a significant amount of gaming content started popping up but it was almost all about modern RPGs and/or Maliszewski's creative projects (e.g. Thousand Suns).
It was January 10, 2008 when, as far as my skimming reveals, Maliszewski made his first post dedicated to Original D&D. It was two sentences long and titled "Things I Learned From OD&D". This post was rapidly followed by a succession of OD&D-related posts including the classic "Kill the Cleric":
"Lest anyone think my respect for gaming tradition prevents my being an iconoclast when warranted, I offer you this: D&D would be better off without the cleric.... If, as I contend, D&D is primarily a game of pulp fantasy and if you want, as I do, to see it return to its roots in a powerful way, there's really no choice. The cleric must go."By March 2008 Maliszewski had started Grognardia to focus on OD&D-related material and The Schizonomican was shuttered by October. In sum, it appears that the seeds of Grognardia were planted in early 2008 and really only grew into a dedicated blog in mid-2008.
Now let's look at the origin of Jeff's Gameblog. Rients started blogging on February 25, 2004 on tripod.com. From day one his blog was called Jeff's Gameblog and was completely devoted to gaming. On his first day of blogging Rients is talking about 80s RPGs including D&D Expert Set, Call of Cthulhu, and Heroes Unlimited. As far as I can tell this is the first glimmer of retro-RPG consciousness in the blogosphere (please correct me if I'm wrong).
If there's anything I can discern about the evolution of Jeff's Gameblog over the last 7+ years it's that the early exclusive focus on games gradually expanded to include more general retro pop/geek-culture material, especially 1980s stuff.
So what does this all mean? Probably not much, but I do think Jeff Rients deserves a ton of credit for being one of the true founders of OSR blogging. Probably the first, in fact... by a long shot...