Okay, Apos…I’m gonna assume you’re still familiar with the basic premise.
Roland trailed the Man in Black, Walter, through the desert in “The Gunslinger.” Along the way, he killed the residents of a town (whose name is eluding me) in self-defense. He met up with Walter, after meeting Jake (a child who died in New York, and awoke in a way station in Roland’s world). He sacrificed Jake in his pursuit of the tower. He holds palaver with Walter, and falls asleep. When he awakens, Walter has been dead for many years.
Roland is attacked by lobster-like creatures at the beginning of “The Drawing of the Three.” He loses the first two fingers of his right hand, and his right big toe to one of these creatures. Infection sets in. Roland stumbles upon a door to New York, with the words “The Prisoner” written on it. He opens the door, and steps into the mind of Eddie Dean, a herion junkie. After a shootout in New York, Roland draws Eddie into his world.
He has to perform a similar feat with Detta Walker/Odetta Walker, a woman with multiple personality disorder (her door reads “The Lady of the Shadows”). She is also wheelchair-bound from an accident years before in which she was pushed in front of a subway train. Turns out the same man that pushed her, Jack Mort, also dropped a brick on her head years before, which led to her developing her multiple personalities.
Roland successfully draws her into his world, and succeeds in merging her personalities into a new one: Susannah Dean. She and Eddie fall in love.
Roland finds a third door, “The Pusher.” Upon entering, he is in Jack Mort’s mind. Mort is also responsible for Jake’s death, where he was pushed in front of a car.
Roland forces Mort to commit suicide by jumping in front of a subway train.
At the end of “The Drawing of the Three,” Roland has completed his task of drawing Detta/Odetta/Susannah out of the shadows, and has started training Eddie and Susannah to become gunslingers.
In “The Wastelands,” Roland is slowly going insane. When he killed Jack Mort, he stopped Jake’s death. However, he had already encountered Jake (at the way station). Jake is in a similar situation in the New York of his time. Jake finds a key, and keeps it (also a book of riddles and a book called “Charlie the Choo-Choo”). Eddie has a vision, and starts whittling a key of his own. Both of these keys are necessary when Jake is drawn into Roland’s world, as well.
During their travels, they discover a billy-bumbler named Oy. Jake adopts him as a pet. When crossing a bridge, they run into a man named Gasher, who appears to be dying from what Roland calls “whore’s blossom.” He forces the party to hand over Jake, to take to a man called the Tick-Tock Man. Roland does, reluctantly.
Roland and Oy trail Gasher and Jake, while Roland sends Eddie and Susannah to find Blaine the Mono, a monorail that should help them in their quest to get to the Tower.
Roland and Oy manage to rescue Jake, and meet up with Eddie and Susannah at Blaine’s station. Blaine, however, is at least semi-sentient, and is suicidal due to the death of his companion train, Patricia. Roland convinces Blaine to spare their lives if they can win a riddle contest against him. “The Wastelands” ends with the foursome on Blaine, about to start the contest.
At the beginning of “Wizard and Glass,” the contest is won when Eddie starts asking “dead baby” riddles. Upon their departure from Blaine, Roland starts to tell some of his past. His romance with a girl also named Susannah, and the trouble that followed, as she was to be the “consort” of a nobleman in Gilead.
It’s been a while since I’ve read “Wizard and Glass,” so I need to refamiliarize myself with it before I try to tell you more.