Off the top of my head, Hector Hard Mode from Fire Emblem 7 was pretty tough, but also very engaging. I'll probably try it again sometime.
Getting as high on the Super Meat Boy Steam leaderboards as I have- mostly with Naija- took dedication and patience.
I haven't tried in a long time, but I could never beat the original Prince of Persia, or its sequel, when I was younger.
I remember the first Alma fight in Ninja Gaiden gave me plenty of trouble.
Beating the Elephant in an old ImagiSoft PC game called Wari...good times.
Beating all of Lode Runner: The Legend Returns was pretty tough, and definitely a marathon. Level 149 is one of the hardest levels I have ever played in a puzzle platformer. Well, except user-created levels. I made a set of truly sadistic, unfair levels, with layouts based on the background images for each world. A good exercise in deeply understanding the mechanics of the game, but of course no one could complete them without rote memorization. Be glad that I didn't know what a backup was and my hard drive crashed, so unless I try to recreate them from memory (hell no), I can't share them with you :p
The last few levels of Buster Bros. games always seemed difficult. They probably still are.
Psychologically, playing through every level of Icebreaker. That game was tedious. I can't believe I convinced myself I had to play through that whole game. Geez.
Learning how to play Smash Bros. Melee competitively was an enormous undertaking, but also one of the most rewarding things I've ever done. If any of you play the original 64 Smash Bros. on Kaillera, drop me a PM sometime :p
The secret exit of Flood Fright Night in Rise to the Challenge (oh snap)
Getting the Super Suit in Super Mario RPG is something I tend to have trouble with.
The last wall in Okami (in Kamui). Oh wait, I haven't done that.
Getting over 200 takedowns in a single race on Silverlake South in Burnout 3: Takedown. The music alleviated frustration ^_^
Beating the Enigma table in Epic Pinball was a real accomplishment for me the first time around, and it's still fairly difficult.
Doing an almost-Crusader-only run on Hard difficulty (Gamer mode...someday) in U.N. Squadron, which I've uploaded to Youtube. What's that? Why isn't it 100% Crusader-only? Hey, why don't you try beating the cave boss without vertical specials?! Sheesh.
Beating Turtles in Time in over 20 minutes (oh snap) (disclaimer: random approximation)
Clearing hard difficulty on all the story mode chapters in F-Zero GX was...well, hard.
Psychologically, going through the ghost ship in Rogue Galaxy. I shouldn't have bothered.
Trying to understand how it all ties together in Chrono Cross.
Psychologically, unlocking everything in Mario Kart games. I just can't do it anymore.
Learning how to play Master of Orion II as a young teen. But wow, that's easily one of the best games I've ever played.
Taking breaks from Oblivion the first time around. That world really sucked me in...
Saying goodbye to my first playthrough of Xenogears, which I played parallel to watching the entire Rurouni Kenshin anime series. What a combination.
Getting a pearl cluster in Hexic HD (hey, it's an accomplishment for me :p)
Surviving Baten Kaitos' voice acting (very nice game though)
Beating You Have to Burn the Rope. So difficult.
Getting past the rabid bear in SkiFree. Oh wait- ARGH
You know, just getting through the Myst games was really tough for me! I had to look up hints all the time. Still, I remember doing one level of Myst III: Exile all by myself, and I was so proud XD
Resisting the power of Peggle. That's one mistake I'll never make again.
Finding someone to play the PC game My Little Furries (or some title like that) with. What an obscure game- I would be EXTREMELY surprised if someone knew what I'm talking about here.
...Well, that was quite the laundry list, and I could probably come up with more, too! :p
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