@JesseSanX That's probably the disabled Safedisc/SecuRom thing. Microsoft basically decommissioned the system all of that generation's games use as CD copy protection check system. Apparently they deemed it a security risk. By doing that, they inevitably broke a ton of older games.
More info: http://www.howtogeek.com/230773/how-to-play-pc-games-that-require-safedisc-or-securom-drm-on-windows-10-8.1-8-7-and-vista/
Cleanest way around is to change your Windows Update settings to not install new updates automatically, then find the "installed udates" list, and uninstall update "KB3086255". Then, check for updates and it'll reappear, and then you can disable it permanently in the list so it won't be automatically reinstalled. After that's done, you can set the updates back to fully automatic (if you had them that way).
It's even worse on Windows 10; the system isn't disabled there but actually completely missing. The only way to get these older games running there is basically, a no-cd crack 🤨