awalterj: It's extremely rare that I replay games and the only 3 I can currently think of are not on GOG.
1.
The Secret of Monkey Island (only adventure game I've played more than 3 times and never get tired of)
2.
Transport Tycoon (most criminally addictive managerial game ever, only Sim City 2000 can compare)
3.
Diablo 2 (of all the low down primitive games this one is probably the most gratuitious and the most addictive)
Out of those 3, I only truly love Monkey Island, the other 2 are more like drugs rather than games.
The original
X-COM comes in 4th in terms of how often I get back to it despite the fact that I like it more and think it's a better game than the ones I've listed above.
As far as the GOG catalog is concerned, my top favorites are
Incubation, Little Big Adventure and Worms 2. But I haven't returned to any of those games since I originally played them.
I'm guessing you never played Act III as a barbarian.