There's indubitably other candidates that I'm not remembering presently, but the first that comes to mind is probably FNaF 2. The amount of luck required to defeat any night past night 2 is unbearable.
Something similar to Greybrynn
It was called Meet the Blockheads or something. Imagine literal 2D Minecraft with permadeath (you can pay a microtransaction to get your character back) and multiplayer
In terms of popular games I'd have to go with Outlast, if it weren't for the occasional nice little details, really good middle segment (which I won't spoil) and fantastic lighting it might even be comparable to the actaul worst game I've ever played Anoxemia.
Anoxemia tricks you into buying it with it's alluring store page and right after shows why game devs prototype before making their game.
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Literally is a copy of Minecraft and doesn’t run well