Hardest Game You've Played?

Mhmm. Perhaps Killer 7 in hard mode? One of the bosses (some sort of doll) was just impossible. I eventually gave up on it (I had already finished the game in normal mode, so....)

 
I can't really nail down one, but a very memorable one was CoD World at War on veteran, particularly the last two missions. For two reasons: an insane amount of grenades (I did the math, 700,000 grenades per hour on average for several hours) and an infinitely respawning Nazi in the only piece of grenade-free territory on the map that I came to name Ted and blame for the grenades.

 
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Skyroads/Skyxmas is memorably challenging for me. I never beat the last road in Skyroads, and only beat the last road in Skyxmas once.

 
Another annoying one was Contra.
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I loved Contra! And of course I could never beat it
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Sim City 4 is slow and tedious. I preferred Sim City 3000 where I had less control but at least I didn't have to play at a snail's pace the whole time.

But for a very long time Ace difficulty (above Expert or Hard) in Ace Combat Zero kicked my ass- until something clicked, and then the ass that was kicked was the game, not mine
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Find me a dogfight 1 vs. 30 and watch me come out unscathed.

 
Minecraft. (joke)

The most challenging game I've ever played is probably Super Meat Boy.

Also, I've noticed that a lot of games I've found hard mostly due to shoddy gameplay. I couldn't complete Asphalt 5 due to the opponent AI being 50x faster than me all the time.

 
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