I know literally nothing about table top games nor do I know anyone who plays. Which game is the gateway to playing to playing tabletop?

NM. I thought you were talking of computer games.

The latest, fifth edition is the most beginner-friendly. It got its faults, but far as just getting into it goes, no other comes quite close.

Basic Rules free PDF, https://dnd.wizards.com/articles/features/basicrules is all you need to figure if it's for you and try something. Player's Handbook is the logical next step if you're sure you want to get into D&D.

If you want to host a game, grab Dungeon Master Guide and Monster Manual, but if you intend only to play, you don't need them.
Everything else you can go for a while without.

As for computer games I reckon anybody interested in D&D ought to play Neverwinter Nights 2 for its distilled D&D experience and Planescape Torment for its fantastic story, at least. They're based on older, more complicated editions, and they aren't even as rigidly adherent to them as some other games, but they're the best gateways I can think of.

OP Whiffles,

Clarify what you're looking for a bit more?

Which GOG Dungeons and Dragons game is most beginner friendly to maybe get you into understanding how to play the tabletop game.

Neverwinter Nights (1), set to fully turn-based, tabletop-reflection mode (I forget exactly what they call it) is a pretty strict [though not 100%] implementation of the D&D 3rd edition [best "crunchy" RPG to me, except Pathfinder 1st Edition, which are seen in Owlcat's games -- PF1e is basically "D&D 3rd Edition 2nd Edition"].

However, ACTUAL play at the tabletop strays far from mechanics and certain other things are more important... The social bits. Improvisational thinking, imagination. Some older text-based adventure games might help with those. Learn/play improv games with people [including board game distillations of them that have prompts and whatnot].

At the table -- good tables anyway -- the latter are more important than the rules crunch. People can help you with the rules crunch during play, but not as easily with the social play bits.

There are writers out there who do blog posts (or videos) that are "scenes in a movie as they would have been played in an RPG". Only links I have on hand is for the Fate RPG (which is VERY different from D&D), but here's an example: https://station53.blogspot.com/2014/07/avengers-accelerated-invasion-begins.html or https://www.reddit.com/r/FATErpg/comments/460yty/fate_core_battle_spiderman_vs_aunt_may/

Aside, while note a specific tabletop RPG, Fallout 1 or 2 or Arcanum definitely function mechanically a lot like ttRPGs. For combat, you could play sRPGs [like Fell Seal] to get a feel for the ideas of character building where you have a broad palette of options and are trying to find things that work together well.

I really don't think that's a beginner friendly game. It kinda just throws in there, with possibly the most involved, arcane and complex version of the D&D rule set, and says "good luck, shithead".

I feel like Neverwinter Nights 2 is probably the easiest to get into, though not necessairly a great one to learn from about tabletop. It's been a long while since I played it though.

Tomb of Annihilation, unfortuantely not available on GOG, would perhaps be a good introduction, since it's adapted from a board game that was created as a gateway to tabletop D&D. Not to mention comics, like Darths & Droids. It's all of Star Wars as a tabletop game.

To me Baldur's Gate and the single player Campaign of Neverwinter Nights 2 were two of the same kind.

To me BG was more straightforward interface wise than NW2, with the rules optimized enough and a dynamic combat, all of this prepared for the pentium computer.

I experimented BG as the first modern CRPG focused in easy to use and quality of life features. I am surprised when this game is called old school.

NW2 (but not the original) was more complex in interface, cameras, character progression and general management. Therefore i'd choose BG for a very beginner. Obviously based in my experience