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[Tharwen]

For a completely free game, try Spelunky. I've never managed to pass the first few caverns.

The good bit is that it feels like genuine difficulty, as almost every threat in the game is one that you can see coming, and you generally only die when you do stupid things like trying to jump across a gap that's far too wide or steal from a shopkeeper (they all have shotguns).

Also, it's procedurally generated.

[EuchreJack]

Try this modded version of Liberal Crime Squad: http://www.bay12forums.com/smf/index.php?topic=46637.45

Not only does your founder start out worthless, but the mod uses a version of LCS with the confusing and difficult "Attitude towards violence".  You have to time your raids just right, or the public will hate you.

There was actually a version far worse, in which your founder was worthless, all recruits were worthless, and death of founder automatically meant death of the organization.  But then I found out that liberated liberals (sweatshop workers, servants, etc) were unaffected by the curse, and boom.

Also...

Do you like X-Com?  How about X-Com: Apocalypse?

Well, somebody made a mod to X-Com Apocalypse where you play the Megapol police and X-Com has joined the aliens.  The helpful police patrols have been replaced with X-Com's violent attacking patrols, X-Com will always have three hidden Advanced Aircraft that will attack your own if you get too close, and the Aliens will bring Megaspawn (that elite alien unit that you only have to face once in standard X-Com Apocalypse, and has been compared to the Heavy Weapons Platforms of previous titles) into the third or fourth battle you fight.

I've never gotten past the first week, and I even made the roads invincible, and activated the building security to support my efforts.  I doubt anyone has played it, let alone beat it.

Megapol mod for X-Com Apocalypse: http://www.strategycore.co.uk/files/index.php?dlid=779

But you've got to somehow get the computer game X-Com: Apocalyse, and get it to work on a modern PC...a challenge in itself.

[baruk]

King of Dragon Pass
Think Oregon Trail in a fantasy setting. Part of the difficulty involves becoming accquainted with the lore, the other part is a management juggling act. Definitely a game you need to start playing on easy. Still fairly challenging to complete the final objective even when you've figured out the ropes.

For a free recommendation:
http://www.wesnoth.org/
 Playing the campaigns on hard, and any of the survival scenarios will be a serious test of your strategy mettle.