The most obscure game that I have for real is probably either Space Station: Silicon Valley or Body Harvest, two grossly underrated N64 games by DMA design (who also made Lemmings and GTA).
On PC... realMYST is fairly obscure, and certainly very hard to come by here in the UK. Then there are games like The Last Express and Toonstruck which are hard to find now.
Of course, if we count games I that weren't obtained through strictly legal methods, then the list gets more impressive. On PS1, I have the little known forerunner to Nippon Ichi's trilogy of sublime PS2 Strat RPGs, Rhapsody: A Musical Adventure, and an RPG/dating hybrid in which you play a vampire who has to seduce a mortal girl with a certain aura and suck her blood called Imadoki No Vampire: Bloody Bride (only released in Japan, but I got a translation patch)
Most obscure PC game I've downloaded is probably The Adventures of Lomax the Lemming. Damn hard to find, that one was.
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