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[gimlet]

The Syndicate expansion was pretty bastardly iirc, especially if you didn't use the "clown car full of persuadertronned fodder" abuse...

[GlyphGryph]

I didn't find Ikaruga that bad, honestly. But then, I play some of the more hardcore bullet games so a console game can really only be so difficulty.

There was one bullet hell game I loved that I can no longer remember the game of. It was interesting in that yo could not shoot back - it was survival only. My best time (longest survived, not level beat) on the hardest level was... 34 seconds? And that was after days of trying and was one of the top times!

[MaximumZero]

I didn't find Ikaruga that bad, honestly. But then, I play some of the more hardcore bullet games so a console game can really only be so difficulty.

There was one bullet hell game I loved that I can no longer remember the game of. It was interesting in that yo could not shoot back - it was survival only. My best time (longest survived, not level beat) on the hardest level was... 34 seconds? And that was after days of trying and was one of the top times!

What. Just. ...I don't know what else to say.

[dwarfhoplite]

what about QWOP? i never learned to run "the real way"

[Trapezohedron]

Not too sure... but you might want to try Elona (a roguelike). It's quite easy in a sense, like identification not being a significant factor in the game, or that permadeath is non-existent.

The game however, has horrible balancing issues, but it's still playable and it's widget value might keep you playing it for a few days or so.

You will still die, though. A lot.

[Yodamaster]

Play Solo Queue ranked in League of Legends.

[Virex]

Not free, but have you tried Devil May Cry 3 on Dante Must Die difficulty? Alternatively, look up the codes for the highest difficulty for Tyrian2000.

[Singularity125]

*whistles and innocently hides the fully cleared very hard difficulty file on his memory card*

Yeah...I'm fucking insane in case you haven't noticed.

I salute you, good sir. I'm bad at basically every game ever. I'm a gamer, but not a good one. >.> That being said, I found Far Cry 1 punishingly difficult, and I know it's a common complaint on higher difficulties. It expects you to be stealthy, then makes it near-impossible to do so. It's not free, but reasonably cheap (ten bucks on Steam). I also second the notion of Elona, but if you want challenge, play it as a pure mage. The magic system in that one is quite unfair. You can never permanently learn a spell, for starters. Sadly, most of the games I play and know are RPGs, because I am bad at games. Grind is not the sort of difficulty you probably want, so I'm out of ideas.

[Virex]

Another interesting one, although again not free, would be the first 3 Rainbow Six games. Set the difficulty to max and disable auto-aiming and you'll feel like you're playing X-com: The FPS...

[Galick]

Loving the suggestions so far, and I already play Elona

I'd like to avoid shooters though, really just not my thing.

[Virex]

In that case, how about Ground Control? That game can get pretty tough on the highest difficulty level.

[MaximumZero]

Speaking of X:Com...TFTD on Superhuman was a nightmare.

[Bdthemag]

If your fine with playing a horror game, im going to have to suggest Pathologic. Extremely creepy, very hard, and poorly translated from russian. Its the kind of difficulty where you can barely survive.

[Farmerbob]

www.fantasticcontraption.com

Even the free game has a couple challenging levels until you really learn how things work.

Once you start to really understand it, the free 21 levels are easy, but THEN you start trying to finish the levels within various limitations.  Smallest number of pieces.  Only certain types of pieces.  No pieces remaining on board after winning.  Etc, etc.

Game has some depth, even if you stick to free.

The free version is loaded up with adcrap though.

$10 to buy the full game including the ability to create your own levels for others to play with.

[Angel Of Death]

Manhunt 1. It's very, very hard. It's not free and is banned in a lot of countries, so good luck finding a copy.