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I've been trying to remember the name of this one for years. It wasn't anything special, but it bugs me when my searches for old titles come up totally blank.

Game engine was on par with Wolfenstein 3d and probably from the same era. Everything was 90-degree angles. Game took place within the walls of a large town. I think buildings had 2nd floors. Large sewer system running under the whole town.

I believe game began with animation of an empty rowboat against waves on a beach.

Character was able to purchase one of three suits of armor at the beginning of the game, and that was it. Didn't seem to affect gameplay.

Character was able to join various guilds around the city. Had to quit certain guilds to be allowed into others. Guilds offered advancement quests involving long treks through the city and often raids on competing guild buildings. Advancing in a guild gave your character special abilities. For instance, a thief could climb through windows to gain access to otherwise unavailable locations. It was possible to advance through every guild by quitting previous memberships. There was some sort of endgame battle in a corner of the city.

What I remember most is that passerby would sometimes attack you at random. They would start with a randomly generated insult like "You look like a rotten tomato." I think you could insult them back. Some very odd insults were possible.
I don't know much about Ultima Underworld, but it was one of the earliest (if not the earliest).
Strife?
Nope, not Strife. Pure medieval fantasy setting. And Strife's Doom engine was way too advanced compared to this.

Not UU either. Totally different game. This one was pure hack&slash plus town exploration.
Legend Of Valour?
http://www.mobygames.com/game/lands-of-lore-the-throne-of-chaos
Post edited June 30, 2011 by ViolatorX
Eye of the Beholder?
Lands of Lore?
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aymerict: Legend Of Valour?
I think this is correct answer - but movement was 360' turnable, not only 90'

http://www.youtube.com/watch?v=M1nK1scE7J8
Post edited June 30, 2011 by Lexor
Shadowcaster? http://www.ravensoft.com/gamesdetail.aspx?xmmid=624&xmid=4&xmview=2

Or possibly Bram Stoker's Dracula?
http://www.mobygames.com/game/dos/bram-stokers-dracula_/screenshots
Witchaven?
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aymerict: Legend Of Valour?
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Lexor: I think this is correct answer - but movement was 360' turnable, not only 90'

http://www.youtube.com/watch?v=M1nK1scE7J8
That's it, nice job! I wonder why my various searches on Mobygames came up short.

I kept remembering it as Lands of Lore, until I finally looked up Lands of Lore one day. I guess the title is similar enough to make that mistake.

Movement was 360, but all the structures are built of same-size blocks, like in Wolfenstein. All the corners are right angles.