Morrowind & Final Fantasy IX.
Why? Because they're fucking cursed!
Morrowind by itself is like a kiss of death upon a computer, as since I bought it the week it was released, installation of which has resulted in dying hard drives, burnt out motherboards, more than a few other system/component failures (including a power supply that spewed out a hefty chunk of black smoke one random day.) This is over the course of the original copy, a GOTY edition my friend handed to me, and I'm even going to blame it for frying my old Xbox as well.
As you can imagine, after a while I really got wary of installing it, but when I shrug and do it's BAM! New computer time.
Final Fantasy IX, it... she is more evil in regards to my life. I can happily say that since I bought it, also first week, the only reason I had to buy another Playstation was because an old roommate decided to skip off with mine. I've enjoyed it thoroughly, never seen a hint of a glitch or hiccup, and get nicely involved in the story.
And then I get the message to Insert Disc 4.
That disc has never ceased to throw my life into upheaval whenever I start playing it. An employer once closed down. More than one living arrangement quickly fell to pieces. Freakin' Hell, I even had a flood in my appartment once the day I got to that disc. Unplanned shit happens, everything gets thrown into disarray and I have to put everything else aside until it gets settled. So, by the time that I can once again spare the time for gaming (well over a month later usually) I turn on FFIX and forget what the hell I was doing. I can't remember the plot point I'm at, I can't remember the characters skills or how I had them built (at a point where combat is more challenging which really makes it a problem), and I just don't remember what had happened up until then.
So I decide to take a break from it, play a different game in the meantime, and eventually start a new playthrough of FFIX. Rince. Repeat. Scream in Rage.