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[Aqizzar]

Duke Nukem II.

Jesus Christ.  I just found my demo of that the other day.  I'd love to find a full version, or anything of Duke Nukem 1.

I'm not sure what the most obscure game I've ever played was, but probably some old NES games like Iron Tank and Faxanadu.  Blake Stone maybe, Oni if it counts as obscure... and of course old Atari crap.

[deadlycairn]

I actually played an old 2d Duke Nukem, don't remember what number it was though, when I was really young. About 5 or so.

[Dakk]

The first version of the rampage series, for the atari.

EDIT: Whoa, CthullhuMUD looks fun, I oughta try it, get bored of it, and get back to HellMOO.

[Cecilff2]

Wacky Funsters
And its sequel Geekwad

Bunch of amusing minigames with trivia and humour thrown in.

[Virex]

On a bit more recent note, I distinctly remember playing Dark Reign. I'm even pretty sure I should have it lying around somewhere. Also, Nox comes to mind, though both of these may not be as obscure as the aforementioned games.

[Idiom]

Do we have to name a really old game? I know a really obscure recent couple.

Soldiers of Anarchy

Spoiler (click to show/hide)

Like Fallout Tactics, but the story was a little cooler and the tactics was more hardcore with your unit's dying in under a second or two of gunfire. Plus it was 3D and had decent animations (though stuff was somewhat lackluster) and had one of the most badass looking game menus I've ever seen.
FAQ

By the same company is the most obscure game I've NEVER played (But desperately want to).
The Fall: Last days of Gaia

Spoiler (click to show/hide)

I can't even find a review for it, let alone a copy of the game itself. It's been out since 2005, but only in Germany. It's like Soldiers of Anarchy, but more RPG free-roamish and better AI (Such as auto-behaviors) and a MUCH better engine and graphics. Also has an open ending like Soldiers of Anarchy did. It was SUPPOSED to be released outside Germany... like FIVE freaking years ago.
FAQ
Some gameplay footage.

Found an actual review/thread, or at least something more than one sentence. Sounds like the combat sucks compared to Soldiers of Anarchy.

[Boksi]

I remember playing this old game called Fallen Haven. Got a demo off some cheap "100 games" CD, you know the kind. It was a simple Science Fiction strategy game and was probably what sparked my interest in the game. Even if it was only a demo, but back then all I had was a very crappy old Windows 95 computer. It was only slightly younger than myself and the screen was so dark I could hardly see anything.

I enjoyed it, though. Never managed to conquer a second province, never mind the alien capital, but it was fun.

Then two years ago I dug up that disc, and using a little compatibility settings magic, installed it and managed to take that second province. Ha! Take that, alien scum!

But yeah, I doubt anyone knows it. Incredibly obscure old game.

[cowofdoom78963]

I have played more obscure games then I have games that people know anything about!

[Dakk]

Oh yea, I totally forgot about Silver, a fun little action RPG by... Infogrames (I think?) with combat I have never ever seen again in any other game, it was fun as hell, even if it lacked some of the core elements for a true RPG, the combat made up for it. Seriously, look it up.

Plot? Boring.

Progression? Linear for 90% of the time, you can do some sidequests to get extra stuff, but thats it.

Graphics? Pseudo 3d scenery (ala Resident Evil), with simple nicely animated 3d figures for characters. Really pretty for the time it was released.

Combat? Very inovative and addicting.

Gameplay time? I'd say 20 hours after you get used to the combat and go after every single hidden thing.

Worth a try, but I dunno if its freeware by now, and if it isn't, good luck finding a copy.

[Idiom]

Is Sanitarium obscure enough?

One of the few games that outright disturbed me.

[Itnetlolor]

I think Zillion would qualify. I LP/Speedran that in a livestream broadcast (link is in my livestream topic).

I think Eric the Unready would also qualify as an obscure adventure game as well. That was pretty fun.

I think Castle Hassle also had to be pretty obscure for the Commodore 64.

[Puck]

The Fall: Last days of Gaia

Don't. I got it, and it's one of the most dissappointing games ever.

It's so utterly sad, because it looks like it could be so much. It has everything you want from your average doomsday RPG, at first glance. But then it fails to deliver so hard, as if they were trying to fail. But you can see they weren't really trying, they were just too dumb to make that game right.

The good press it got, well, my theory is, that was german magazines pushing their own folk.

The enemy AI, for instance, does NOTHING but approach you until you are in range and then fire. I think (not sure), if you're grouped, they might try grenades. But that's it, I kid you not. The "AI settings" for your party members are basically a joke. Especially given how the enemy AI acts.

If you're not in for the combat but for the story, you might be equally dissappointed. On top of that, the original german voice acting is so bad, its beyond description. It's so bad that I actually think you got a good chance the translations are better. (I think they didnt use proper voice actors, but a bunch of teenage programmers, which tried to make their voices sound all rough and grownup...)

The only thing good about the game was... well, I dont know. Sometimes the locations look nice.

tl;dr, keep imagining how cool that game is, but never ever destroy that beautiful illusion by actually playing it.

contribution to thread:
http://www.mobygames.com/game/amiga/flood/screenshots , for instance

[Ampersand]

Chex Quest.... 2.

[Buddybud]

"colonial conquest" - It was a game for the Commodore 64. It was a multiplayer world domination game. Kinda like risk but more akin to axis and allies. All players input their moves in secret then all moves and battles were done simultaneously. The only way to see enemy units was to attack or to spy, which gave mixed results. Though 30 years old it still had better game mechanics then any other game of the sort i've played since. Me and my friends in high school  would drink in one room and had a separate war room to input our turns, discuss alliances and watch the battles at the end of each round. Great fun since you could never really KNOW the outcome till it happened.

[HideousBeing]

Chex Quest.... 2.

Chex Quest isn't obscure... everyone had it (and loved it!). Chex quest 2 a little more so. chex quest 3 on the otherhand is much more obscure (get it!) Gotta find a link somewhere... AHA!