I wanted to buy Fallout 3 recently for another play through. It's only six years old, but apparently works with such difficulty on Windows 8 I didn't bother. At least it could still be played on an old console, though. Not a piracy matter, I realize, but it's interesting which games can and can't be played nowadays. The first game I ever played on the 286 still runs on Windows 8 I bet, but many in between don't.
On Vista or newer, install
all Gamebryo games from Bethesda or Obsidian
outside of Program Files. It's not Windows 8, it's
any Windows post-2003. Even if it runs stably, it won't be able to read and edit all files correctly, causing mods to screw up, and even the stock game audio (I was accused of pirating it on this forum, FI. Later, I found the default install location was the problem--WTF, Bethesda?). When I say all, I am including new installs of Morrowind.
Then, go download a tweaked INI. Havok and AI thread settings often need to be changed from default for 3+ core PCs to keep it stable, and sometimes to even start it. They didn't carry that degree of consolitis over to Skyrim, thankfully, but it's very bad with Fallout 3. Worth it, especially with the DLCs, IMO, but pretty bad that you have to do all that to get and keep it working.
P.S. Most programs as old as for a 286 will likely not run at all in 64-bit Windows, without an emulator like DOSBox, or for popular cases, modrnized game engine reworkings. The switch to NT killed compatibility for many, and then the switch to 64-bit killed compatibility for more. But, despite the development focus on retro games, DOSBox works for, "serious applications," as well.