It used to be Super Street Puzzle Fighter II Turbo (as in the PSOne version of the XBLA version) but sold it recently for a helpful chunk. At the moment its probably Parasite Eve II or ICO.
The original Medieval Total War and Shogun Total War. I haven't seen either in stores for years, and I also haven't seen either available for digital download.
I've got a boxed copy of Sim City by Maxis with a "Software and manual" copyright date of 1989. The game is on two 5.25" floppy disks and one of those new-fangled 4.5" diskettes (imagine that - what took two big disks to hold can fit on one smaller disk - how'd they do that???). It includes a maroon sheet of paper with black lettering (so it can't be copied - oh how clever!) with codes to be entered every time the game is loaded.
Tatics Ogre for the PS1. 70+ dollars for a copy on Ebay. Paid $15 from a friend.
Story goes
My best friend sold the game to another one of my friends for 10 dollars. He had purchased it for 5.
I bought it off of that guy for 15. Haven't let it out of my sights since then.
Pokemon Silver. It's not a generally rare game, but the fact that it can still save makes it pretty awesome.
I've also got a copy of Majora's Mask with the 3D sticker on the cartridge. I sold my N64 years ago, but I still have MM.
Unfortunately mine is a reproduction copy, so it is clear blue instead of grey, but even so it probably is my rarest game. Also because not only are the originals very hard to find, but also if you do find one they are expensive on a ridiculous level. The last one on eBay I saw went for about $15,000. Not as much as Winter Games but still rather expensive.
Oh, I also have a boxed copy of Shaq Fu. I just bought it out of curiosity and it is as poor as you might imagine.
I own more rare consoles than rare games, most of them boxed. Not so long ago, I bought a Limited Edition Pikachu GBA SP, it was the only one on eBay so I had to snap it up.
EDIT : I'm currently watching a mint condition, factory sealed copy of Stadium Events on eBay. It is remarkably cheap so far at £165
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