I'm not including DOS based games that may have been re-issued for Windows, but games that were created for the Windows platform.
1. The oldest I think I have loaded is the original Panzer Commander, which was developed and published back in mid 1998 by the now defunct Strategic Simulations
When I bought my new rig last year, I kept my old WinME based rig with an older ATI card to maintain as a legacy rig just to run these old games. I have also purposely not upgraded the graphic drivers for this older rig in over two years just to help avoid graphics anomalies that can happen with these older games.
The resolution for this game is fixed at 640 by 480, so the terrain and structures are pretty simplistic, but it still plays well and all the German tanks are just as much fun as i remember to operate.
2. I also loaded up an old EA game called RECOIL from 1999. It's a sci-fi tank shooter by Zipper Interactive (they also did the first Crimson Skies for Microsoft). The cut scenes are live action videos shot real fuzzy with lots of static to make them look like some sort of strange transmissions from underground rebels.
As you progress through the game your tank gets upgraded to also operate as a hover craft, an air boat, and a submarine.
3. Next I have the above mentioned Crimson Skies that came out in 2000 loaded and play through the levels occasionally. IMHO it is still one of the most fun and entertaining arcade flight games ever made.
4. Another that I have loaded that came out in 2000 is the original SeaDogs by Akella. It was one of the first and in my opinion still the best attempt to take the original Sid Meiers "Pirates" style game to full 3D with campaigns for each of the colonial powers and outstanding "age of sail" pirate naval battles.
I also play it off and on with a neat mod that adds several new campaigns, quests, and other features to the game.
5. Finally, I just loaded up Freespace 2 by Interactive, also from 1999on my new rig. It was a bit more sophisticated in the graphics area for the time and it seems to run with no poblems on my new rig.
I have never finished the entire campaign, but I have vowed to do it this time. It is still consider by many be one of the best, if not the best, space sims ever made. Original copies of the game are scarce and used to sell for $100 and up on E-Bay. I think the code was finally made open source, and it may be available as freeware now.
So--what's your oldest PC game that you play on a regular basis?
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