5. A Confederacy of Dunces
What's the story? Ignatius J. Reilly is 30, lives with his mother, and believes that Medieval philosophy justifies his obscene flatulence and astounding dickhelmetry. He spends 400 pages making life miserable for everyone he meets. Toole killed himself before the novel was published, and Will Ferrell has been trying to make a movie happen since 2003. Hell with it, just make the game already.
How might the game look? Want to give audiences quirky characters in offbeat adventures? Make Confederacy of Dunces a SCUMM-style point-'n'-click. Just put your highbrow literary-pedigree hat on and add a meter that determines how badly the character needs to fart.
Until then... The amount of games known for being genuinely, quotably, laugh-out-loud funny is still pretty low. There's Monkey Island, of course, and Sam and Max, and Day of the Tentacle... Basically, familiarize yourself with the entire LucasArts back catalog while you wait for this one to get off the ground.
4. Naked Lunch
What's the story? A series of loosely-connected anecdotes about getting crunk in a variety of inventive ways, Naked Lunch is pretty big on “individual interpretation” at the expense of “making a damn lick of sense.” In any given college dorm, there is one guy who can explain Naked Lunch to you better than we could; never, ever party with that guy.
How might the game look? Naked Lunch the game would bring back the “text adventure” genre for a whole new generation of impressionable youngsters. It would then kill the genre stone dead by making said youngsters type “ingest Mugwump semen” in order to get to the final area.
Above: It's always a treat when we get to run screenshots this exciting
Until then... Infocom's Steve Meretzky cranked out a slew of these sort of titles in the 80s: pairing up sci-fi satire Leather Goddesses of Phobos with futuristic political thriller A Mind Forever Voyaging would probably feel a bit like playing Naked Lunch. Particularly if you were tripping balls at the time.