The short version: The Phantom Tollbooth, given the psychological treatment of American McGee's Alice. Scroll to the bottom for a complete list of pictures, which I will update as I upload them.
The Lands Beyond were Milo's wonderland growing up - the happy place representing his loves and fears in life, where he retreats when life seems pointless to remind himself of his goals and interests - the fantasy reflecting his reality.
Milo grew up. So did the Lands Beyond.
Life has slowly driven it into him that there are things that ought to be more important to him, that a dreamer and a visionary is not well-enough adjusted to the world around him to live. And so he has slowly cut ties with the Lands for the sake of his own well-being - sacrificing his sense of wonder for socialisation, his sense of adventure for financial security, his sense of purpose for a certificate of achievement.
Halfway through college, it falls apart. No matter where he is he wishes he were someplace else, doing something else. He feels no connection with his 'friends' and no accomplishment in appeasing the ceaseless demands of his teachers or his ever-changing supervisors at work. He locks himself in his room for a week and does nothing. If anyone tries to get his attention, he doesn't notice. He wraps himself in his bed sheets and drifts in and out of consciousness, watching everything around him gather dust.
After who knows how much time has passed, he's visited by the Whetherman - his curiosity/boredom, whom he has ignored since well before this little episode, unkempt and unfocused and clad in a prison uniform and chained to balloons. He wants to do something. Anything. It doesn't matter what because anything would be better than this mindless idiocy. Milo, of course, doesn't see a point, but the Whetherman manages to rile him into a fight (a combat tutorial section, but he starts blowing exploding bubbles once sufficiently damaged), then kicks him through the door. Nothing is outside; Milo plunges through the sky from what now resembles the Castle in the Air, clutching to a few of the Whetherman's balloons, as the Whetherman himself floats gleefully up and away.
He lands in the Doldrums - a mute grey wasteland of dust, battered by winds carrying ash and scraps of cloth, concealing fantastic ruins and massive rusty detritus that just barely protrude above the dunes. The chief enemies to be found here are the Lethargarians, brass-shelled snails with human faces that don't move except to latch on when you bump into them (Milo's first weapon is a magnifying lens he took from his room, which he uses to smack at things as well as to reveal invisible secrets). The place is a wide-open quicksand box - a beautiful scrapyard of the centuries, but no obvious goal other than to evade Malice, the bobbing gorgon who slowly pursues you. Progress only comes by choosing to explore; the ruins are vertical, an enormous dustbin of history with ruined skyscrapers and half-buried passenger planes on top and architecture that becomes steadily more ancient the deeper you manage to go, funneling you towards a barren circular structure resembling a mixture of Stonehenge and the Delphic Tholos. A familiar-looking pile of worn brass clockwork and filigreed plates in the shape of a forlorn Doberman is asleep in the middle, with a prominent key protruding from his back that practically begs "Wind Me".
Tock is very happy to see you! He knew you'd return eventually no matter what the rest of the kingdom thought, and now that he's waited so patiently and you've finally returned he's sure he'll be able to help you get everything straightened out because, wow, have things really gone to pieces again while you were away. He accompanies you throughout the rest of the game, filling multiple roles as an assistant, hint provider, save point, and weapon - something of a combination of the Cheshire Cat of American McGee's Alice with Huey of Haunting Ground. He is loyal, vicious, sensible, straightforward, more than a little passive-aggressive, and appreciates simple pleasures. Like automobile rides. On the subject of which... He herds Milo over to a nearby dune and starts to dig, revealing a small teal motorcar. After a puzzle or two to get it working and clear the exit - the very bottom of the funnel of history is obstructed by Hate, who with Malice signifies Milo's self-loathing and self-destruction - he and Milo set off to more civilised districts...
At this point the concept starts to get fuzzy - there are a lot of ideas I've thought of but not settled on (which is probably okay because this entire thing is so far beyond my skill level to create that it's not even funny):
- The various domains visited would include Dictionopolis; Digitopolis; the Wilderment, including the Forest of Sight and the Soundkeeper's Castle; Ruined Wisdom; Conclusions and the Sea of Knowledge; and, of course, the Mountains of Ignorance. Probably not in the same order as the book - I've an idea that Ruined Wisdom is actually the final area, now that the Senses Taker has moved in and set up his headquarters there, attempting to build a skyscraper tall enough to catch the Castle in the Air.
- I'm not sure yet what's become of Rhyme and Reason - I think perhaps they're not on speaking terms with each other. (Rhyme without Reason is a dispassionate, babbling Ophelia; Reason without Rhyme is a paranoid and obsessive moody wreck.)
- The Wilderment is a mixture of memories and feelings Milo has revolving around his various abortive attempts as an artist. (Chroma is an optional boss, caricaturing an art teacher with whom Milo had creative differences.) Milo is guided through the domain with the help of Alec Bings to the Soundkeeper's Castle, which resembles a blend of art gallery and Animusic performance hall, with undertones of Aperture Science, and is patrolled by the Awful Dynne. (Your reward in this section are the Gatling Bagpipes. They work like Alice's Pepper Grinder, with a cool-down based on Milo's lung capacity, which slowly grows the more you use them.)
- Conclusions is a flying island - hence why you usually have to jump there - suspended by propellers and filled with whimsical science, with heavy reference to Myst and Gulliver's Travels. Canby is here, as despondent as can be, and Milo convinces him to fight off an invasion of the demons of ignorance led by Hindsight - an enormous, hulking bipedal toad, fought in Conclusion's engine room, which is full of moving parts and other hazards to both he and Milo. He invariably leaps before he looks, so the object is to lure him into mangling his tongue between gears or landing on something painful.
- Azaz's strategy to defeat Ignorance entails accumulating all the knowledge and information into the royal library - for it is these things that make our kingdoms bastions of civilisation rather than the demons' lands of lawless savagery! - but in reality he has abandoned his officials to fend for themselves. Parts of Dictionopolis are claimed under the conflicting jurisdictions of Officer Shrift's police force, the Cabinet's palace guards, and Madame Macabre's market regulators (carrying Chicago typewriters and dressed sharply in pinstripes and fedoras, with a little slip marked (R) tucked in the brim), all fighting the subversive influence of the agents of the Everpresent Wordsnatcher. Azaz must take his archives and put them to use, if the city is to be saved before the Wordsnatcher deems it ready for the Flame Doctors.
- Digitopolis is a triangular prismatic skyscraper, surrounded by pit mines in the shape of the Mandelbrot Set. The way in is by the Number Line - a tarnished silver maglev powered by crystals and steam, conducted by the Dodecahedron (tall, slender, and angular, in a white uniform; his large head is dark translucent blue, and each of the twelve pentagons has an emoticon printed on it in white). The Mathemagician very much loves his job and has no delusions about the threat posed by Ignorance, but is frustrated by constantly having to subordinate his love of puzzles to practical considerations and feels that while he's done what was necessary to keep his kingdom from succumbing to Ignorance he questions whether giving up so much of his love and pursuit of knowledge in the meantime has not just made him indistinguishable from them. He detests how Azaz has turned inward and just tidies his books, letting his kingdom be overrun around him, but also envies him and longs to pursue the subjects that actually fascinate him.
- With his Pen and Pencil, in a kilt
- With the Perspective Lens
- With the Gatling Bagpipes
- With Aunt Faintly's Box of Letters (Combat Modes)
- The Knight of Mirrors
- The Starving Artist
- The Doldrums
- The Mountains of Ignorance
- The Wilderment
- King Azaz, the Unabridged
- Sergeant Shrift
- Aunt Faintly
- The Cabinet
- The Everpresent Wordsnatcher
- Flame Doctors
- Ruined Wisdom
- The Dilemma
- The Senses Taker