There must be a disturbance in the Force, my turn again and it isn't the 10th yet!
For my first game I would like:
Chessmaster XI: Grandmaster Edition (PC)
I too was looking for a chess game to take, and this is a very highly rated series. From wiki:
For the second pick, I think I want to take a truly 6 degree of freedom game:
Descent II: The Infinite Abyss (1997) for the PC.
I loved the original Descent and this one when they came out, zipping along underground corridors blasting enemy ships to bits. The 6 DOF means you can hover in place and move in any direction, including up and down, independently (like a space ship or helicopter). You can also get very disoriented easily, so it takes a strong stomach and sense of direction to play this. Ooodles of fun. The newer version has fancier graphics, but isn't as much fun to play based on what I have read (haven't tried that one myself).
This version of the game includes the expansion pack, so more corridor-flying goodness for me!