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I have a few I can think of off the top of my head.
The second to last boss of Hallow Bastion in the original Kingdom Hearts. I bet he wouldn't be THAT hard anymore, but when I first fought him I was doing it for a friend and I didn't have the game yet.
Speaking if which, the next one was for the same friend. I was playing the Mercenaries mode in Resident Evil 4 after NEVER having played it before. I ended up spending the whole afternoon getting all S ranks (or whatever ranks they used) to get his ultimate reward.
Back in the day every Snes RPG I beat felt like an accomplishment, games like Secret of Mana, Chrono Trigger and FF6.
Oh, once when I was little I beat Donkey Kong Country in 2 hours. Not any sort of record, I know, but when you're only like 10 years old or less and you aren't THAT great at games, beating a game you hold in high regard as fast as you can feels like an accomplishment. Plus I STILL got my homework done that night!
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When I beat Jak 2. That game was hard, especially for little 10 year old me.
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One of my greatest moments was playing Darkcloud one. I was in one of the lowest floors in the final required dungeon I got trapped by two enemies who pincer-ed me. I was able to attack back and fourth at each enemy with a steam of attacks and beat them both. It felt freaking awesome.
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Getting a million point score in SSX tricky for the first time, when I was a youngling, that was insanely hard for me to pull off. Somehow I ended up getting it with Marisol, who is one of the worst characters in the game who sucks at tricks.
I cried man, I fucking cried.
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Unlocking all characters and stages in Super Smash Bros. Melee. The one stage that eluded me? You know the one... you had to beat 10-Minute Melee to get it. My thumbs throbbed like hell after spamming B+Down with DK.
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Beating Final Fantasy 10 and 12. The final bosses are long and hard. But both of the ending are the BEST ENDINGS I'VE EVER SEEN.
'' A true hero never dies!''