My experience of weird and borderline insanity games mostly came from Jerma985's stream, they're so out-of-this-world that I need to apply eye drop to make sure my eyes didn't just Event Horizon'd me.
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Strawberry Magic (MS-DOS). Nothing much to say honestly, my brain forcefully went into Hibernate Mode 10 minutes into the video, but this game might be the Elden Ring of its time.
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Odama (Gamecube). This is uhh, voice-controlled pinball game set in feudal Japan where you Takeshi's Castle your way to the victory. The control alone could rapture "modern audience" in an instant as they witness the ball eliminate your finite army more than the infinitely spawning enemies. And to make matter worse (at least from what I observe), your army from previous stage carryover to the next plus extra bit, so the worse you play = the harder the game gets.
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Seaman (Dreamcast). Another voice-controlled game, but this time it's about raising your human-faced fish in tamagotchi-style, as the Seaman growth, you can ask mundane question, philosophical question, and even threatening them to be cooked at rich restaurant and served them to rich family. "The Dreamcast f**king s*ck" as one guy said.