If you want to get into some free gaming history, one thing I noticed is there are a lot of community projects maintaining the more popular games on MyAbandonWare.

Check the links and comments on the game page and do some research online about any game you want to download.

The games I've downloaded from MyAbandonWare have been fine, but they've been original rips of the CDs with only a few cracks and patches. Sometimes they just crash on startup or are missing some dependency.

The more popular games have maintained versions made to work on newer hardware with better resolutions.

There are downloads of all the Need For Speed games on MyAbandonWare on other sites with mods and updates preinstalled to work better on current systems. The same goes for games like the No One Lives Forever series, Tribes, Midtown Madness, and the original Silent Hill 2.

There's even projects for other free games like Marathon, Bungiee's FPS before Halo. Marathon is free on Steam now as well, but you can play it off platform on more systems through the community maintained freeware version.

These are also great ways to play older games without needing to use an emulator, so you can play them without the resource overhead of later emulators because you're running a native version or at least a port of the game instead.

That way you only need to worry about compatibility mode or trying to get games working through WINE for obscure titles that don't work and have no support.