There was an old PC game called “Dominus”. I don’t really know much about it. My dad just randomly picked it up as an xmas gift one year for me. It was pretty sweet.
You’re the lord of a kingdom that gets invaded by like eight armies. You have your own monster units you can deploy. You can deploy traps. You can cast spells. You can go down and fight hand to hand. If they make it to the throne room and kill you, it’s game over.
If you capture enemy troops, you can interrogate them. There’s a little animation where they get poked with a red hot iron poker. If you capture a leader, you can sometimes negotiate peace. If you capture an enemy mage, you can learn part of a secret spell. I never got a secret spell working, though.
It was super cool. Never met anyone who’s played it.
Back in the 90s maybe into early 2000s, my family managed to acquire a lot of VHS tapes, and some of them were fairly obscure
Two that I remember particularly fondly were 2 animated movies
Epic: Days of the Dinosaur, which was about 2 kids raised by dingos, kind of a weird fantasy movie
And Return to Treasure Island, which was pretty much just a straight-up if somewhat comedic adaptation of Treasure island, which was apparently made the USSR, and the Russian version had live action sequences that didn’t appear in the English version I had.
In 1997 the creator of Ren & Stimpy had a (somewhat) interactive flash based comic called The God Damn George Liquor show. I have that still. It’s definitely out there strange and not constrained by cable tv Standards & Practices. Highly enjoyable for what it is.
How about Wally Gubbins? A series of silly skydiving videos. My father has a ton of them on VHS. I loved it as a kid. I just looked, you can even find them on YouTube. So maybe not that obscure.
In terms of software I remember having several ad games. So, games that are basically just an ad. I had a Bifi game. Some weird game about colours where I don’t remember what it was for. And a “game” about Chesterfield Cigarettes. I remember that I had to install QuickTime Player to run it. It was basically like Google Streetview when you walked into buildings with a few interactive elements put in. No idea where I got it. Might even still have the CD somewhere.
When I was a child I saw a stop motion animation called 3 Little Pigs Sing a Gig. It was this rather surreal, felt puppet musical of the aforementioned nursery rhyme.
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