I've got some DOOM WADs I have been meaning to play so I would probably grab Trench Foot, Total Chaos, and the sequel to Ashes 2063, Ashes: Afterglow with a portable install of GZDoom to play them.

After that I'd probably bring Star Trek TOS and a MOBI copy of Neuromancer by William Gibson combined with a portable install of VLC and Calibre in case the computer didn't have applications that support the file format.

What about you?

I wanted to phrase this in a way where it isn't a prolonged or desert island style question where the responsible idea would be to bring Wikipedia ZIMs and educational PDFs. It's just an awkward amount of time to kill. The mid 2000s office desktop stipulation is just an additional challenge so you can't just bring in a copy of Baldur's Gate 3 or Cyberpunk 2077.

Edit: By mid 2000s I meant around 2005; the XP or Vista.