One particularly hilarious part was right at the beginning of Island of Dr. Brain, back in the old-school days of manual-based copyright protection. The game would give you longitude and latitude coordinates, and you had to look them up in the manual to figure out where you were supposed to parachute. If you got it wrong, your character would just splash into the ocean.

I actually referenced The Island of Dr. Brain in something I made about a year ago. I don’t know if you played it, but it has a jigsaw puzzle as one of the mini-games. It was one of the most unusual jigsaw puzzles I’d ever seen: an animated jigsaw, where the entire image was a effectively looping "cinemagraph". One of the first things LLM-assisted projects I put together was a jigsaw puzzle game with about a dozen custom animated jigsaw puzzles. Link is in my profile.

This is a bit of a deep cut, but my most distinct memory of Super Solvers: Midnight Rescue in DOS was that it used the PC speaker to play “The Sorcerer’s Apprentice.” If you did anything that triggered a sound effect like jumping the music would immediately reset and start over. It was like a weird, primitive version of scratching a vinyl record as if you were some kind of amateur PC-speaker DJ. (and kind of the opposite of Dig-Dug)

I think they became less interesting because they became more homogenous, more standardized, more commercialized

It's like the internet. It was more interesting when everything was spread out and you felt like you had to explore it. Now it's all the same content collected on the same 5 sites, and it feels like there's nothing actually interesting out there anymore