My two:
Very cliché, I played Ocarina of Time a ton as a child, have memories of playing it both on N64 as a wee child and on game cube as a less small child. Never got past water temple even with the game guide.
Yu-Gi-Oh forbidden memories. Played the crap out of that game on play station, constantly playing on free play praying for the cards I would need to get further. I was never able to beat more than 1-2 of the high mages. Watching speed runs on the game it turns out I was never ever going to beat that game as a kid. The final 6 are just disgustingly brutal.
xcom 2
Battletoads
Earthworm Jim
Shit, I’m dating myself.
Oh Jesus. Battletoads is a really good example. Man fuck that hoverbike level. Holy shit.
I did that level so often that you could put in front of me now and I’d pass it.
This doesn’t answer quite what you asked, but what comes to mind is The Legend of Zelda: The Adventure Of Link for the NES.
I had a Game Genie as a kid. And for some reason I could not get past the boulder to get out of the first overworld area.
It wasn’t until quite a few years later that I figured out some of the Game Genie codes in the official Game Genie code book could have permanent affects on your save file. I had apparently gotten the hammer (which was what was required to break the boulder), but before breaking the boulder, I used a Game Genie code to swap the Hammer for some other item I wasn’t supposed to get until later in the game. So, I was stuck without the ability to break the boulder.
More to what you were asking, The Adventure Of Lolo was a good example. I was pretty young when I first picked it up. Decided it was too hard, and basically never touched it again until adulthood. In adulthood, I loved it.
Lara Croft tomb raider on Play Station 1
Splinter Cell Chaos Theory. My brother and I would play split screen, and we always hit a point where we had no idea where to go
