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[beorn080]

If it has a vid card, give Mechwarrior 4 a try. It should work.

[nichaey]

Well see how he likes the games on there, but next round (assuming he wants more) I'll probably throw stronghold, warcraft 3 and mechwarrior 4.
I might try that dungeon crawl stone soup, if it's as easy to learn as you say I'll put it on as well.

[Tarran]

Stone Soup is still a roguelike though. Make sure your friend likes dieing first before introducing him to it.

[Lokii]

Umm... Morrowind worked on my (incredibly low end) 2000 desktop. It may work on his laptop, if you turn all the settings down to the very lowest, although the water may flash white.

[Bouchart]

Civ 2?  Simcity 2000?

[nichaey]

I actually own a simcity 2k disc...and 3k, their installation is pending my lazyness/cd key

[Helmaroc]

I was running a pretty old computer for a while, here are some suggestions. Keep in mind these old games can be kind of abstract, clunky, and a lot of them you either will love or hate. Mid-post EDIT: I just read your update. If your friend doesn't like them maybe you will.

All the early Maxis stuff, SimLife (my favorite), SimAnt (also great), SimFarm, SimEarth.
Any kind of roguelike should run...Nethack, ADOM, ToME, IVAN, maybe Incursion.
Liberal Crime Squad.
If Morrowind is too shiny, maybe Daggerfall would work and it is free now. They even give you DOSbox instructions.
Doom. This may or may not be a valid download, but worth a try.
Wolf, Lion.
UnReal World will probably run, and is dirt cheap (demo is available also).

If I think of more I'll add them to this post.