Most of the rocket barrel stages from Donkey Kong Country Returns. Love that game and I'm a huge fan of the series, but the area where you have to escape a bat firing lasers from his mouth on a rocket barrel is one of the most frustrating gaming moments ever.
(I do realize this game came out 10 years ago so idk if it's classic but I suppose it contributes to the theme of the thread. And DAMN IT'S 10 YEARS OLD TOO! Remember getting it for Christmas!)
Reserved for classic gaming discussions.
As for beating a ridiculous challenge? Finishing Dragon's Lair for NES felt pretty darn good. So did getting a perfect score in Pitfall!, in my case the Intellivision version.
I’ve never played the Intellivision version, but I imagine that’s quite a feat. It’s tough as hell to get a perfect on the VCS version. I have to imagine the Intellivision controller makes it that much harder.
Donkey Kong Land II, SLIME CLIMB. For the life of me I could not beat that blasted level on my original Game Boy for almost a year. Late one night while staying at my Grandmothers, I managed to beat the stage, and was sweating bullets to beat the rest of the stages (and the boss) of the area so I could save. I was so ecstatic that I beat the stage that I forgot that I could save at the Kong Kollege with the coins I earned to beat that stage in the same area.