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Most difficult-to-the-point-of-broken game I've encountered would be Lunar 2: Complete. Right around the time I reached the Blue Dragon - who has high defense, nasty group-striking moves, and the ability to arbitrarily heal himself by several hundred (or is it thousand?) points every single turn - I decided life was too short to waste trying to prove myself to Victor Ireland and his HARDCORE tendencies.
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If you thought Lunar 2: Complete was hard, you would have broken multiple controllers if you ever played the Sega CD version. I remember Vic stating that it was TONED DOWN for the US version as the Japanese version of Lunar: Eternal Blue (Mega CD not, Saturn/PS1) was over three times the difficulty. (Borgan = you're his bitch in the SCD version. Gravity Bomb cheap shot FTL))
Hardest I would have to say...
Ecco the Dolphin. Seriously, is there a fucking way out of that first level? (Not really, but I just get too frustrated and stop playing after 5 minutes trying to figure how to advance)
Silhouette Mirage (PS1). The game has to start out on the hardest difficulty, you'd have 9 lives and have to beat all 5 paths (with just those 9 lives) before you can unlock the "secret options" which includes a difficulty adjuster. Me thinking you had 9 lives each play through. LOL!! Don't get me wrong, the game was fun but I could murder WD for upping the difficulty that bad.
Another WD trend would be Vanguard Bandits. Maybe it is because I'm ass at RTS games, but that game was just waaaay too difficult for my tastes. I think I made it like on the 3rd chapter or whatever and haven't picked it up since then and that's been about 10 years.
I'm pretty sure there are others that are just sadistically hard that I've played, I just recall off-hand.
Jam it back in, in the dark.