The oldest game I've played lately is Civ V.  Once Civ VI comes out and if it's a true successor, then Civ V will collect digital dust in my Steam library.

Bought a couple more old big box PC games.
1) Jetfighter III by Mission Studios, never used, complete in box.
2) Aces over Europe by Dynamix, complete in box (has 3 3.5" floppies).
3) Traitors Gate by Dream Catcher Games, never used, complete in box.
 
The first two are for my very small collection and Traitors Gate is to be played (read that it works fine on Windows 7, haven't tried it yet).

I dug this out this morning. Great game with awesome music. Wish somebody would remake with good graphics.
 
 
 

I finally got Tachyon: The Fringe working on Windows 7.

I played older Games but only after 2007.
I play Left4Dead2 orderly.

Brad_Hawthorne

fearpoint
Absolutely not. Way too many good games constantly being released on PC to fart around with games that old.

I'm not a fan of paying to beta test new releases for the first 6 months of a game title. I've found much more fun in playing 1-2 year old titles where you know what you're actually getting vs throwing money at the hype machine.

OP mentioned a game over a decade old. That is far different than 1-2 year old games. My fav game right now is coming up on it's 1 year anniversary.
 
What I currently have installed
 
Anno 2205
Cities Skylines
Battlefleet Gothic
The Crew
Killing Floor 2
Overwatch
GTA5
Total Warhammer
Mordheim
Battlefield 4

Tribes 2 for me

I'm not sure this qualifies as an older game.... Skyrim. Every time i exit, the screen goes black, and i cannot get back into windows. Only way around it is to hard reset. If i CTRL+ALT+DEL and go into task manager, close it that way, that works too. I have done the whole file file verfication within Steam, didn't do anything. If i use windowsed mode while running skyrim, it will close fine. This is the only game it's doing it in. Anyone have any ideas? 

New PC games, whats that?

So does Baldurs gate count? Skyrim might not count anymore once the new version drops, but the content is certainly old. Now to wait for mods and skse to update for it.