[I] was wondering if you could give some advice for a beginner looking to try out some classic D&D.There's a lot of ways you can go starting some old school action and my answers here will only be one guy's opinions, but I'll take a shot at it. Here's my take on the four key components for embarking into the wondrous realm of kicking it old school.
I started playing in 2nd edition(think Jeff Easley cover of mounted warrior riding through a desert canyon) and have played plenty of 3.x , so I have absolutely no experience with this great stuff you keep talking about. What would be the best bang for my buck? What books do I need? Would love to know what you would recommend as a starting set.
Component One: Attitude
This is the key to the whole affair, really. If you nail this you could use lots of systems (including the 2nd edition AD&D Sam started with) to produce useful results. To get in the zone I recommend reading Matthew Finch's Quick Primer for Old School Gaming. It's free and wicked awesome. Not every grognard will agree with everything written there, but it's still great stuff. Get your players to read the Quick Primer if at all possible, so you're all on the same page. The number one lesson to learn here, in my opinion, is that whenever the rules, your notes, or a module are silent about something then it's you and your players job to make something up. And most importantly, that sort of on-the-fly invention is meant to be the best part of the game. Try not to lose track of that whenever something comes up that isn't covered by the rules.
Component Two: Rules
The rules you pick aren't as important as what you do with them, but there's three basic angles of attack in picking a ruleset. The hardcore choice is to go straight to the beginning, with the original version of D&D. For six bucks you can get PDFs of OD&D at DriveThru and here's a link to some great instructions on turning those PDFs into your own Little Beige Books. But if you go OD&D you need to be prepared to do some extra work. You can't just skim over the rules and start playing right away without a lot of heartbreak. This is a work that requires attentive reading and active interpretation. I personally find that very rewarding, but if you are itching to play right away there are better options.
Labyrinth Lord is my pick for the best ready-to-rumble version of D&D currently in print. It's a retro-clone of Moldvay's near-perfect '81 Basic/Expert rules. Some purists will claim that the Golden Age of Old School was already dead by the time Moldvay's D&D rolled out, but personally I rank purity of essence a lot lower than making sure the rules rock the block. You can snag a free PDF version of LL here or swing on over to this Lulu link to buy a print version. I've got the Lulu softcover and it is totally sweet. If you or your players rankle at the idea that Elf and Dwarf are classes as well as races, then the 1st runner-up in this pageant is Basic Fantasy a.k.a. BFRPG (Free download here, print edition here). Unlike Labyrinth Lord, BFRPG doesn't exactingly emulate any particular previous version but it sorta lives in the same neighborhood as several older (A)D&D editions.
The third route to go is to find a d20 game that imports some old school elements. I don't really recommend this route, but I mention it because you might have players still stuck on the d20 stuff. Castles & Crusades is one good d20 option. I personally dig the C&C Collector's Edition boxed set. The rules are slimmer than the full-blown hardbacks but it's an all-in-one affair with monsters, treasures, and a tiny little module. When running C&C try to keep in mind that the Attribute Check rules are just one handy tool, not some universal resolution system meant to cover every situation. Another extremely cool d20 option is the Microlite 20/Microlite 74/Hard Core M20 family of tiny d20 rules.
That's probably more options than Sam wanted when he asked, so here's the short answer: Labyrinth Lord.
Component Three: A Dungeon
I consider it axiomatic that D&D requires both dragons and dungeons. And I don't mean monster lairs with six or seven rooms all rationally designed with complete ecologies, I mean big honkin' crazy ass dungeons. Your absolute best bet is to design your own dungeon, perhaps using the random dungeon stocking charts in your rulebook of choice. If you want to start out with a prefab dungeon, here are some good options, organized by rule set.
OD&D offers several interesting options. Issue #2 of Fight On! has the first level of "The Darkness Beneath", a megadungeon that's being created as a collaborative effort. If you go with OD&D, you're pretty much going to want every issue of Fight On! anyway. Erroneous Grog has a couple of adventure downloads available (scroll down the page a bit). And I wrote a little number called Under Xylarthen's Tower that might do you some good.
For Labyrinth Lord I recommend doing some digging over at Dragonsfoot. DF has some great stuff in the Classic D&D downloads section that ought to be highly compatible with LL. I recommend The Haunted Keep. Honestly, I don't know Basic Fantasy well enough to recommend BFRPG-specific modules. Can anyone offer a little help here?
Castles & Crusades: Castle Zagyg. 'Nuff said.
If you go with M20/etc then looting the rotting corpse of 3.x will get you down the road with this one. I suggest starting with Goodman Game's Dungeon Crawl Classics line.
Component Four: Sandbox Setting
The short definition of "sandbox" is "full of useful, immediately gameable crap". Again, Fight On! magazine should be of use if you go with OD&D. Issue #2 has a great little sandbox by Rob Conley and James Maliszewski. Or if you want to make your own sandbox issue #1 has a great article helping explain how to do so. For Castles & Crusades the Castle Zagyg setting book, Yggsburgh, is pretty effin' sweet. If you can hold off a few more weeks James Mishler of Adventure Games Publishing is finishing up his Southern Reaches gazetteer for C&C. For Labyrinth Lord I suggest downloading The Phoenix Barony. If you can track down the Wilderlands of High Fantasy boxed set and the accompanying Player's Guide they would be a good match for the M20 family of games. And Points of Light would make for excellent setting for any set of rules you settle on.
(Most of these setting book are extremely light on rules and you could mix-n-match beyond my recommendations. I'm pretty sure I could run the Wilderlands with OD&D or Yggsburgh with Labyrinth Lord with little difficulty, to give a couple examples.)
When you settle on a dungeon and a sandbox don't forget to place the dungeon in the sandbox somewhere close to where you plan to start the PCs. Ideally pepper the surrounding landscape with some smaller dungeons as well. Add a dragon lair if neither your dungeon nor the sandbox include any. Trust me on this one. You need a dragon.
Now that I've finished this post I can't tell if I've been helpful or if I've muddied the water by giving too many options. Anybody else have any other suggestions for Sam?