That at least fits into the picture of the game being fun is basically only true on a meta level.

Yes, but in a way they were quite ahead of their time: Just take any random game from today with at least a bit of storytelling and chances are high that you will get such "dilemmas" with similarly pointless results.

My issue with these is that they finally discourage free exploration of the game world. The more you move around, the more you are obstructed by those ultimately pointless questions. So actually they punish you for playing without a walkthrough.

Well, I eventually switched to a virtual machine too, because I just want to play my games in full screen mode.

Some further impressions:
-) The choppy character movement was kind of irritating at first, but come to think of it, it really suits the show. Just think of all those Terry Gilliam sections!
-) It might get a bit tedious after a while, but at least at the beginning it is fun clicking at random things and discovering pure weirdness (Oh fishy fishy…).
-) I love that moral dilemma questions! Just textbook examples for how stupid those normally are.
-) That Live Organ Transplant section… wow, don't know what to say. Seems really dark to me, cannot imagine that this would pass any kind of censorship today. But it reminded me of a game that left quite an impression: "Life and Death". Now that is one I have to dig up sometime and review.

I think I last played it in a Windows 98 virtual machine.

Let us know how far you get - but save often, it becomes gradually more unstable.

Since I am currently rewatching the series I am a bit curious about the game, but I cannot seem to get it started. What setup did you use? Wine starts the game and plays a bit of music, but shows absolutely nothing, Windows does not even want to start the installer (just complains about needing "at least" Windows NT4.0) and I don't want to setup a virtual machine until there is no other option.

Edit: Got it working by emulating a virtual desktop with 640x480 ratio in wine. Wow… what a strange game. Especially those cardboard cutout characters.

Feel free to share anything about Monty Python's The Meaning of Life (1997) here!