Kid Chameleon (Genesis/Megadrive)
Technically I have finished it, but that was via the use of an emulator and serious abuse of the added quicksave option.
Boulderdash I&II (C64)
I swear I have played these for over twenty years and I have never finished either one of them.
Starcraft: Broodwar
Theres this one Zerg mission where you are on an island and you have to flatten the Zerg that are under Terran control and the Terrans themselves. Been stuck on that one ever since I finally gained a copy of Broodwar, almost 3 years ago.
AvP
Is it just me or are those Alien bonus levels running on some kind of hidden, stupidly hard, difficulty setting?
The Sims
What? It counts; I've never finished it. No one has.
Star Trek: New Worlds
A Star Trek strategy game. I was so excited when I learned of its existence. I played it once.
It looks great, I especially love the way the buildings collapse rather than explode when destroyed, or the way the construction drones build everything polygon by polygon as though building it panel by panel, or how the phasers had a real screaming beam of death feel to them, but is was so dull.
And easy. Incredibly, stupidly easy.
I completed the Federation campaign on my first go, went to bed, and have never played it since.
Hitman 2: Silent Assassin
If that ****ing cook on that ****ing japanese level does his "smoke a cigarette in thirty seconds" trick once more I'll ****ing scream.
And if it's not that its the ****ing guard in the garden spotting the ****ing cooks body through a ****ing fence at ****ing night while wearing sunglasses.