A very simple game I've played for dozens of hours in my black and white 1st generation Palm handheld PC was
Space Trader. Somebody ported it to Windows, and now only that version exists since the original developer seems to have gone out of business (though it's easy to find the handheld game with some googling).
You start out with a small ship and travel through space buying stuff cheap and selling it expensive, until you get rich and can take a better ship. There's also some cool side quests. It's inspired in the old DOS game "Elite", though with no 3D. It's very addictive.
The Windows version is very faithful to the original, but I don't like it as much because it looks dated that way. You more or less expect a handheld game to look bad, but not a Windows game. I strongly recommend the handheld version for those rainy days on a bus. The Windows version should be just as good but I don't play it.
Another game that was actually a shareware demo but I played it like there was no tomorrow was Castle of the winds (first chapter). It's gotta have been the best game ever made for Windows 3.x, and I don't even like rogue-likes much. I *think* both chapters were released as freeware now, but I could only beat the first (it took me a few weeks already, but then I was 12).
Edit: I'm favoritizing this thread, lots of good stuff here.