I've caught myself thinking about games I pirated/emulated through my life - which is like, 99% of games I've ever played - and how much absurd bullshit(compliment) I stumbled upon by sheer chance, and felt like sharing some of those, in no particular order:
Wonder J (SNES) - A child raising game, though with a much more rowdy infant than the Princess Maker and its spin-offs. Prince Maker, I guess? Watch as you desperately try to make Pinochio learn to read, only for him to throw the books away or simply rip them to shreds. 10/10 child simulator.
Live a Live (SNES) - Now with a modern remake, this one absolutely changed my mindset regarding dark stories, particularly the ~Extra~ chapter which rewrote my brain fiercely on the entire concept of fated heroes and the world that surrounds them.
Terranigma (SNES) - I have no words for how badly this game broke me, and worse of all the real good shit is almost entirely on its second half, all culminating in an ending so heartwrenching that it mocks the entire notion of 'bittersweet'.
E.V.O. (SNES) - Probably one of my first experiences with a game that is decidedly not good, yet it panders almost exclusively to the specific brain disease I might have. Grind needlessly to evolve each of your creatures body parts and then grind some more, as you evolve towards the end of a scenario only to jump to another era and start the grind all over again. This is where most people would throw their controllers away with frustration but teenager me simply looks amazed, like having another banquet served to him.
GeGeGe no Kitaro (SNES) - I actually rented a physical copy of this, in japanese and everything. I have no idea how this game found its way to one of my local gaming places, I'm just putting it here because this intercontinental travel endlessly amuses me.
Front Mission - Gun Hazard (SNES) - You'd never guess what's the only Front Mission I ever played. Shedding off the strategic RPG roots to go instead into a sidescrolling fare, this is a mecha busting gem, and an exhilarating experience through trekking around the world with your ever growing mercenary company in search of truth, vengeance and more destruction.
Demikids: Dark Version (GBA) - You'd Never Guess² what was the first SMT game I played. While "edgy pokémon" is a very demeaning way to refer to the series, DemiKids was actually their attempt to do something in that vain, even having "Light" and "Dark" versions with different demons you could have.
Zone of the Enders: The Fist of Mars (GBA) - You'd Never Guess³ what was the first ZoE game I played. Instead of high octane mecha action, this is instead a strategic RPG with timed hits. Yup! Whenever you make an attack and target another mecha, you get into a first person screen where you try to aim and hit its 'weak' point, do do extra damage.
Sigma Star Saga (GBA) - You'd Never Guess the firts Waypoint game I played [now I'm stretching this for all its worth]. This is a Shmup jRPG, a completely buckwild concept where you're walking around an overworld map and is suddenly transported to a random battle against a ship. Not a great game but holy heck if it isn't novel. Also my first experience with WayForward's terrific horniness.
Bruce Lee: Return of the Legend (GBA) - This was an amazing sidescroller beat'em up that came out of fucking nowhere and was played by maybe 6 people. Fast paced, brutal and sadly unknown.
Vandal Hearts 2 (PSX) - This is the point where I start to realize the post is getting long and its not even that good. So I'll close with a particular baffling pick. A strategy RPG on the PSX trying to tell a political, dark story, but with one absurd gameplay twist: You and the enemy units move at the same time. That's right, bitches: Every turn, you and and an Enemy NPC move and attack at the same time, meaning that you have to position and attack not where your foes are but where you think they are going to be.