Dungeons & Dragons, original edition, expands on the ideas of Chainmail by incorporating magic and nonhuman fantasy races, moving things from the realm of standard medieval skirmish gaming into what was fast becoming the role playing game. Having a copy of Chainmail to help with running combat is probably a good idea. The image to the right shows the alternate, later edition artwork.
To fully enjoy Original edition D&D, you'll also want to have a copy of Avalon Hill's Outdoor Survival wargame. The design of D&D at this point assumed you owned this game, and despite it being nearly 30 years out of print, huge Avalon Hill print runs in those days make it fairly easy to come by.
The D&D boxed set, pictured above, contained 3 volumes:
Book 1: Men & Magic
The image to the right shows the alternate, later edition artwork.
Book 2: Monsters & Treasure
Book 3: Underworld & Wilderness Adventures
Also included was a collection of reference sheets, usually staple bound together.
This original edition of the game went on to be expanded with 5 supplemental books:
Supp 1: Greyhawk - Not to be confused with the campaign world setting of the same name, this book introduces the Paladin and Thief classes, as well as a variety of new monsters, treasures and expanded rules for combat.
Supp 2: Blackmoor - Although this volume includes an early incarnation of Dave Arneson's signature adventure, Temple of the Frog, it is again not truly a campaign setting primer, but simply another collection of expansion material for the game. The Monk and Assassin classes are introduced herein, as well as rules for aquatic combat and adventures, and guidelines for attacks with specific hit locations.
Supp 3: Eldritch Wizardry - This volume introduces the Druid class, as well as Psionics and encounters with Demons, in addition to more new spells and magic items.
Supp 4: Gods, Demi-Gods, & Heroes - Rules for religious pantheons to expand the background setting of the campaign. Oddly enough, the deities are 'statted up' just like normal game monsters, probably creating the idea among many players that fantasy gods can be challenged and killed for their XP and loot.
After the publication of Original D&D, TSR split the line into Advanced D&D and Basic D&D.
The Basic Rules were then revised and edited by Tom Moldvay, and this edition, along with the David Cook edited Expert Set, is often referred to as Moldvay/Cook D&D or B/X D&D. While the uppermost levels of play are hinted at as forthcoming in the D&D Companion rules, that expansion would not appear until the later Frank Mentzer "BECMI" edition. Still, for many campaigns, the B/X rules cover a broad enough spectrum of play to let it stand alone as a fairly complete game. The Basic Set covers levels 1-3 of play. Note that the box set bears the same artwork as the rulebook pictured to the left, minus the red borders. This edition of the game included the adventure module B2: The Keep on the Borderlands. The image on the left depicts the box artwork, the one on the right shows the rulebook artwork.
The David Cook edited edition of the Expert Rules expands upon the Moldvay Basic rules, taking play up to about the 14th level of play, and introducing rules for outdoor wilderness adventure and naval encounters. Also included are sample maps and notes on the Grand Duchy of Karameikos, the foundation for what would become the Known World campaign setting, also known as the world of Mystara. As noted above, the teasers about the Companion rules for high level play would never see fruition under this edition of the game. This box set bears the same artwork as the rule book, without the blue borders, and includes the adventure module X1: The Isle of Dread. The image on the left depicts the box artwork, the one on the right shows the rulebook artwork.
The D&D Rules Cyclopedia, often referred to as simply the Cyclopedia or RC, is considered by many to be the finest Classic product, if not one of the finest D&D products of any edition, TSR ever published.
The RC is a compendium of the Basic, Expert, Companion and Masters sets from the Mentzer/BECMI edition, containing most of the rules material from all of those products, as well as a greatly expanded primer section concerning the Known World/Mystara Campaign setting. The Mystic Class is also formally added to the standard options, and different systems for tweaking or removing the demihuman level limits are presented. Lastly, the tome includes conversion notes for using it with the AD&D game line, and vice-versa.
Wrath of the Immortals is the expansion to the RC that replaces the BECMI era Immortals set, updating and expanding those rules. Like I mentioned with the Immortals set, if extreme high level play and PCs as gods doesn't interest you, this book is optional.
Wrath of the Immortals, and many of the other supplements and adventures published
during this era carry the "Challenger" logo, which for all intents and purposes simply
designates compatibility with the Rules Cyclopedia.
Throughout the 1990s, TSR published a couple different versions of a basic rules set or boardgame to accompany them and keep the Basic D&D line alive. Most include a variation of a starter adventure called Zanzer's Dungeon, but aside from that scenario, none really innovate or offer anything new, and are generally in the realm of the hardcore collector only, but will serve just fine for a basic level introduction to the Classic D&D game line. The following are thumbnail images of the various sets:
The 1999 D&D Silver Anniversary collector's set included this reprint of the earlier Holmes Basic Rule book. This edition is easily identifiable by the silver TSR dragon logo in the bottom left corner.