This post is inspired by something that +Eric Franklin posted on Google+, asking about From the Ashes, and it inspired me to take a quick jaunt through the various published incarnations of the setting (Gygax's home campaign was originally quite different, but morphed into something more like the published version as time went on). I'm going to focus here on the boxed sets and setting-wide sourcebooks, rather than the specific modules and regional sourcebooks that have been released over the years.
First, of course, we have the 1980 folio. This was the original incarnation of the published version of the setting, and packs a lot into its 32 page gazetteer. There is a broad overview of history, written in terms of migrations of peoples (reminiscent of the late Classical era migrations of the Germanic tribes), as well as capsule descriptions of all the nations and natural features (mountain ranges, forests, rivers, etc.) on those beautiful maps by Darlene. It is set in CY 576.
Many of its fans feel that one of its strengths is its brevity and lack of detail. There are no descriptions of deities or religions (beyond Iuz, because he rules a nation, and even then there are no stats in the conventional sense of the term), no adventure hooks, no NPCs (other than rulers, and all they're given is a class and level). I think modern audiences would probably find such omissions frustrating, whereas we OSR types see them for what they are - room to fill in ourselves.
The folio was followed shortly by the 1983 Gold Box, consisting of those same Darlene maps and two books. The Guide covers much of the same information, in terms of kingdoms and forests, but adds a lot of information on deities, random encounter tables for various regions and nations, quasi-deities, tables for appearance and national origin, and more. Much of the additional material had appeared in the pages of Dragon magazine, but some, such as the mini-adventure seeds, are new to the product.
Up to this point, the setting is what could be called a "classic" fantasy setting. It portrays the forces of evil and good in the world as being in relative equilibrium, has a quasi-medieval/Renaissance feel and level of technology, it can be called a high magic setting, and its relatively low amount of canonical information still makes it very easy for a DM to make it his own without worrying about contradicting something written in some novel or sourcebook (a problem which plagues the Forgotten Realms). There is a definite feel that evil is on the rise, but the situation isn't hopeless and the stalwart heroes can stem the tide through bold action.
1992's From the Ashes, produced after Gygax had left TSR, takes the setting into a different direction and sets a decidedly different tone. While the basics of the setting are still intact - it's still relatively high magic, the quasi-medieval/Renaissance organization is still there, and the canon is still relatively low compared to the Forgotten Realms (but growing, especially with the City of Greyhawk boxed set and the various regional sourcebooks that started to come out after this boxed set was published). The various nation descriptions are updated to reflect what's happened in the timeline between the time frame of the Gold Box and this set (which takes place in CY 585), but the real change is in the tone of the setting.
Evil is now clearly ascendant. Iuz has conquered most of the northern Flanaess, the Great Kingdom has collapsed into undead-fueled anarchy, giants besiege or have conquered the western Sheldomar Valley, demons and devils (tanar'ri and baatezu, ahem) stride the land, and the Scarlet Brotherhood is popping up everywhere taking out leaders and conquering territories. The feel now is that the forces of good are on the ropes, besieged on all sides as well as from within, and evil could triumph at any moment.
Once Wizards of the Coast acquired Greyhawk, they moved the timeline ahead yet again, this time to CY 591, and released the Players Guide and Greyhawk: The Adventure Begins, both in 1998. This time the pendulum swung back to the "evenly matched good and evil" side. Iuz is more-or-less contained, successor states are rising in the former Great Kingdom and establishing (relative) order, the Scarlet Brotherhood has suffered reversals, and the western Sheldomar Valley is being reclaimed from the giants. One gets a sense from this incarnation of the setting that everyone is catching their breath after the tumultuous years that preceded it.
There's also much more of a focus on the central Flanaess and the city of Greyhawk itself in these products, but not so much that they seem to be in isolation. By this time, however, the weight of the accumulated canon (in the assembled adventure modules, sourcebooks, novels, magazine articles, and miscellanies) is starting to tell - inconsistencies are creeping in much more frequently, which is inevitable when so many authors have written so much material for a single setting - but in terms of sheer volume it is still far behind the Forgotten Realms.
Finally, we come to 2000's Living Greyhawk Gazetteer, which was an incredibly thorough and comprehensive treatment of the setting, including an enormous depth of history on all of the territories and nations of the Flanaess, information on deities and religions, NPCs, and more. It is set in the same CY 591 timeframe as The Adventure Begins and the Players Guide, and served as the launching-off point for the Living Greyhawk campaign managed by the RPGA. Because of this, although it adds a wealth of detail (indeed, it might be said that it adds too much, straying the farthest from the original folio in terms of content vs. room for DM invention), the tone of the two earlier books is still maintained.
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