Difficulty-wise, The Lion King on SNES. This game shattered my childhood.
The game was fun to some degree, just required an unfair time investment. The final fight was a memorably bad experience though. I was like eleven years old when I made it to the end and swear I spent almost a full hour clawing at Scar before I figured out that I wasn’t actually doing damage.
I could never get through the 2nd ostrich riding sequence in the 2nd level as a kid. The rest of the game was fine, though, once I used the level select to skip ahead. Turns out, it was because my eyesight was shit and I couldn’t even see the correct obstacles on screen (I was trying to avoid the branches, but no it was pink hippos and bird nests the whole time, so my timing on the double jumps was always off). Replaying the game a couple years back when Disney re-released it alongside Aladdin, I found it still tricky, but doable.
Superman 64 was a hell of a mess
Seconding this one. I was like 11 years old and it’s the first time I can remember being disappointed when getting a game. Went from like Mario 64 to OOT to Banjo to Superman 64 and hoo boy what a drop off.
There are way more rings than that, and they’re actually the best parts of the game. It gets so much worse in the levels without rings. Awful combat, terrible puzzles, inconsistent framerate, and thoroughly unclear objectives.
Oh, and everyone’s favorite: escort missions!
Same as a lot of other gen-xers: E.T. the Extra-Terrestrial
It’s a classic answer, E.T. on the Atari 2600.
That shitty mobile version of SimCity.
Took a beloved childhood classic (the original SimCity) and took a giant free-to-pay shit all over it.