For the amateur game, I would suggest 5 Days a Stranger. It's relatively long by indie-game standards (though shorter than almost all commercial games), it's widely regarded as one of the best home-made adventures, and it is neatly divided into (you guessed it) five days.
Also, people who are so inclined can donate a few bucks to Yahtzee via Paypal, and get access to a "director's commentary" in the game. This would make the discussion more informed.
Oh, as a commercial game, pick Grim Fandango! I haven't played that yet.
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