Blue Chairs

One of my favorite games, Blue Chairs is surreal at its best. It's not surreal for its own sake, but to underpin the emotional state of the protagonist. You are Dante Hicks (no, not the one from Clerks), and you begin the game by drinking a bottle of unknown liquid from a strange man. From there you drift from reality to dream to nightmare to who-knows-what state you're in and back again, but it is all amazingly cohesive.

Dancing in the Dance
You can go anywhere you want. You can see anything you want. Where are you? There are five hundred people crammed into this room -- it's a miracle of genetic instinct and secular humanism that no one's bumping into anyone else, except when they want to, which is always... Why don't you touch people more? You never hug people except when they hug you first. Your grandmother leaving for a trip to New Orleans, to see where her body will reside once she's gone up to wherever it is that grandmothers belong after they die...

Like an interactive fiction version of a David Lynch movie, Blue Chairs manages to be confusing, provocative, beautiful, and in the end packs a surprising emotional punch.