What are some obscure DOS/early windows games that would be fun to check out? I'm looking for stuff more like Under a Killing Moon, Lands of Lore, Beneath a Steel Sky. Trying to avoid the billion Doom-clones that popped up in those days.

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What are some obscure DOS/early windows games that would be fun to check out? I'm looking for stuff more like Under a Killing Moon, Lands of Lore, Beneath a Steel Sky. Trying to avoid the billion Doom-clones that popped up in those days.
may i interest you in Wolf by Sanctuary Woods
https://www.mobygames.com/game/754/wolf/
it's an educational survival game where you just play as a fuckin wolf. it's amazing. and they did a sequel with lions called Lion the next year!
I like the Legend of Kyrandia series a lot, especially the second, hand of fate. Ooh, and Dune 1.
Most of what I played as a Jebling is pretty well known or not in the realm of adventure or RPGs like those. And also this monstrosity of an RPG/Management game:
since i just finished it might i recommend Ultima VI: The False Prophet
You could have a look at: https://archive.org/details/softwarelibrary_msdos_games
Which has loads of games.
Some of personal questionable choices are:
Dyna Blaster is bomberman for pc, Duke Nukem 2 when it was still a platformer, Jazz Jackrabbit 1+2 for even more platforming, Jill of the Jungle for the unconvential transformations the main character has in some stages and Tyrian 2000 for one the better shmups on pc
I don't know if it would qualify as 'obscure' but I'd very much recommend Star Control 2 if you haven't played it.
It's a DOS-era space exploration/action game with great writing, a bunch of different aliens to ally/fight with, and a huge galaxy to discover.
A free/open source port of the game for modern hardware is available at https://sc2.sourceforge.net and that includes voice acting from the 3DO port.
The Santa Fe Mysteries series is interesting if you’re looking for more FMV adventure games
Star Trek 25th anniversary! An adventure title that brought back the original Trek cast (as long as you got the CD-ROM and not the floppy version!) for six new missions. And yes, you can get the red shirt in your party killed in each one if you aren't careful
Oh I had Judgement Rites as a kid. It looks like it's the same exact engine, but different stories.