2nd to OSR


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Like others have said, it really depends on what you want.

Are you looking for something close to 2E? My understanding is that 1E and 2E are about as compatible as any two different editions of AD&D have been, so getting into 1E or its retroclone OSRIC probably would make sense.

Are you looking for a Basic D&D experience? There are a LOT more options, and I'd want to know two things before making a recommendation:

1) What's your experience level? A lot of newer OSR products like OSE and Knave seem to assume that the reader already knows the basics and just needs a really well-organized toolkit. Older OSR products as well as TSR Basic D&D products didn't assume that as often and have more explanation. Are you wanting to start out like a beginner? Go for older OSR/TSR versions – I think I would especially recommend Swords & Wizardry, with the free Swords & Wizardry Quick Start. Are you confident in running an Old School system? Read a few of the Old School manifestos like A Quick Primer for Old School Gaming and grab a newer OSR product because it will be organized better.

2) Are you wanting to emulate a particular version of D&D or are you wanting something that has taken the starting point of D&D and run with it in a new direction? All the original TSR versions have been available for a while as PDFs, but OSR retroclones like Swords & Wizardry and OSE tend to really improve on the organization. Other OSR rules diverge a lot more in specific directions, like DCC RPG inserting a lot of chaos into the game – especially the magic system. What are you looking for?
 


I am going to be a little different with my advice. Look for OSR adventures that seem really new and exciting. This will help narrow your search in a few ways.
1. Helps you find a new that is exciting!
2. Helps you determine what a specific OSR system does well.
3. Maybe a specific OSR system has a series of adventures that are exactly what you want.
And if I truly wanted to cast a wide net I would look at modern, cowboy, and sci-fi adventures for OSR! (Also, the amount of horror can have a huge impact in the system you choose.)
 



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