I have a game that used to work, like worked for a few weeks, and then no longer works on any computer. It doesn't make sense, the disk wasn't damaged, it installs and even if I run patches, it won't launch, and then rarely properly uninstall. The last non-free Tribes game, I think it was called Tribes Vengeance, I really wish I could play it because I love the skiing and jetpack stuff in Tribes but the F2P Tribes Ascend, last I checked, is multiplayer only and I don't want to try that hard, I remember playing the story in Vengeance and while not knowing what was going on, I did enjoy the level design and the combat. I tried installing it several times on multiple PC's, XP and Windows 7. I even, shamefully checked to see if there was a CD crack that might offer a working version, I still have the discs and at the time decided that would definitely make it okay.
Game didn't even have a torrent available, I found an unofficial patch that in hindsight was probably sketchy but it didn't work either.
I haven't had a game that didn't work at all since XP came out, I rarely buy games that I don't check forums to see if they work. I have bought games that didn't work for a time because I didn't check the specs but they later worked, I also have some old games that wont work anymore on Windows 7.
I did have an old game for 98 or 95, Backyard Soccer or something, I was like 8 and it worked for a while but then somehow it decided my computer needed more RAM when I got a certain distance into the tournament mode.