The quest begins when the Hero agrees to help three "wizards" with their game of Hollows and Hobbes. The Hero is shrunk via a magical orb and placed onto the game board. The Hero has to save the Princess and defeat the evil Baron to win the game.
The game begins in Lightwater Village, a small hamlet with very few citizens and no services for the player to use. The "wizards" immediately begin commentating, and continue to do so throughout the quest. The Hero can choose to talk to the villagers (game pieces that are voiced by the three wizards), or skip ahead to Arturo the gate-keeper. He directs the Hero to the baron's "eerie castle" on a nearby hill.
Once the Hero reaches the fortress, two of the commentators complain that the castle is too pretty. One of them fixes this by changing the weather from sunny day to misty night and summoning wolves. After defeating the wolves, the Hero can enter the castle.
The first room of the fortress is a teddy bear making factory (again the third summoner's creation). The baron enters the factory with the captive princess and taunts the Hero before disappearing further into the castle. There is a chest on the left side of the factory, out of which a "wise old man" appears. After a short argument, the commentators decide to skip the customary riddle and give the Hero the "Scimitar of Baron Slaying +3" for free.
After exiting the factory, the Hero comes to a room that is completely empty, save for an inconspicuous and hardly noticeable lever in the centre of the room. Pulling the lever does... nothing. The commentators have a brief conference and decide to start a Hollow Man encounter. During this encounter, the Hero unlocks the "+30% Sense of Self-Importance" upgrade for the scimitar. Defeating the Hollow Men opens the door into the next area.
The next area is a hellish chasm inhabited with Demon Chickens. Either kill all of the chickens, or run past them to proceed.
The final area is back outside the castle. The baron summons waves of elite Hobbe guards to attack the Hero. After defeating the Hobbes, the Hero confronts the baron. The baron warns that he has only one weakness: the Scimitar of Baron Slaying +3. The Hero cuts him down, spurring an argument between the commentators. Two of them complain that you can't kill the final boss in one hit (probably referencing Fable 2), while the other blames the others for giving the Hero the sword so easily. The fighting stops when the commentators decide that to end the game, the Hero must kiss the princess, regardless of the Hero's gender. Once the Hero either kisses or insults the princess, the quest ends.
WARNING: If playing co-op be warned: during the final fight against the elite Hobbes, there is a ledge you must jump off. Be certain player one jumps off first, as letting player two jump first can cause the game to not spawn the next wave of Hobbes. If this glitch occurs, reload your game (you must exit to the dashboard and relaunch), as you are unable to teleport out of the area to restart the quest
- It is a spoof of the fantasy RPG board game "Dungeons and Dragons."