The stories are subtly about the Baby Boomer generation, specifically King's view that this generation (to which he self-consciously belongs) failed to live up to their promise and ideals. Significantly, the opening epigram of the collection is the Peter Fonda line from the end of Easy Rider: "We blew it." All of the stories are about Baby Boomers, and in all of them, the members of that generation fail profoundly, or are paying the costs of some profound failure on their part. The closing "Heavenly Shades of Night are Falling" is clearly meant as a eulogy for the promise of the Baby Boom generation, with the hint of redemption.
The first, and longest, part, "Low Men in Yellow Coats", takes place in 1960 and revolves around a young boy, Bobby Garfield. He lives in Harwich, Connecticut with his self-centered mother, Liz, a widow, and he really wants a bicycle. His mother claims they do not have the money for a bike, despite her constant purchases of new clothing. For his eleventh birthday, Bobby's mother gives him a birthday card containing an adult library card. During this time, Bobby doesn't realize that his mother is having a relationship with her boss. Bobby spends his time with his two best friends, John "Sully" Sullivan and Carol Gerber.
An older gentleman named Ted Brautigan moves into an adjacent apartment on the floor above Bobby and his mother. It is obvious from the start that she doesn't like Ted, but Bobby does. Ted spends a lot of time discussing books with Bobby and gives him Lord of the Flies, which makes a huge impression on the boy. Bobby's mother claims to be worried that Ted might be sexually abusing Bobby, though in fact she feels guilty about neglecting her son. Bobby, understanding the situation but unable to articulate it, solves the problem by keeping the two apart.
Ted speaks to Bobby as one would speak to another adult, which makes a great impression on Bobby. Ted offers Bobby a small amount of money to read him the paper daily, claiming his eyes are not what they used to be. Bobby witnesses Ted "blanking out" several times, and realizes that he possesses psychic abilities, which he is able to pass on to others by coming into physical contact with them. Ted places his hands on Bobby's shoulders one morning and later on that day, Bobby is able to win a three card monte game at the beach because he could read the mind of the card dealer. As the two grow closer, Ted confesses to Bobby that he is being stalked by "low men" or more accurately they are the Can-toi, evil workers for the Crimson King (a recurring villain in King's novels). The signs of these men include "lost pet" signs, and chalk drawings of stars and moons. Ted asks Bobby to keep an eye out for their signs and to let him know when they are near. It is revealed (although it is only understandable to readers of King's other works) that Ted is in some way connected to The Dark Tower. He is hiding in Bobby's town as a means of escaping the struggle revolving around it. Ted makes occasional references to both the tower and its beams, including the field of rose petals that it is situated in.
Bobby does begin to see the signs but doesn't say anything to Ted, not wanting to lose his new friend. One day, he finds Carol lying in a grove of trees with a severely injured arm. She tells him that two bullies, Richie O'Meara and Willie Shearman, held her down while a third, Harry Doolin, beat her badly with a baseball bat. He carries her back to his apartment house, where Ted is waiting. They go inside the Garfields' apartment, and Ted has to cut off Carol's blouse to reset her arm, which turns out to be dislocated but not broken. Just as he manages to reset her arm, Liz, also looking badly injured, enters the apartment. It turns out that her employer and colleagues invited her to a supposed real estate seminar, which was an excuse for them to try and take advantage of her, something that Bobby dreamed of and Ted was able to describe to her due to his psychic abilities. Seeing Carol on Ted's lap, sporting a naked torso, immediately causes her to think Ted has been sexually molesting Carol.
Eventually, Liz calms down, takes Carol home, and decides to sit in the local park to gather her thoughts. Bobby takes a long nap, and when he awakes he finds his mother asleep in her bed, and Ted long gone. Bobby looks into his mother's purse and finds a "lost pet" poster appealing for information on a dog named Brautigan. He realizes that his mother has telephoned the "Can-Toi" (low-men) and told them of Ted's whereabouts. Bobby eventually catches up to Ted, just as the "low men" are about to take him away. They want to take Bobby with them too, but Ted offers to work for them if they let Bobby go. They give Bobby the final choice and, faced with going with Ted, wherever that may be, or staying behind, Bobby chooses to stay.
The remainder of the story details, in brief, Bobby's adolescence. He beats up Harry Doolin with a baseball bat, and moves away from Harwich with his mother, and is twice put in a juvenile detention facility. When he arrives home after his second incarceration (at this point it is 1965), he receives a letter from Carol, with another envelope that she tells him is from Ted. Bobby opens the envelope and finds it is full of red rose petals, the ones which surround the Dark Tower, and he knows that somewhere Ted is free of the low men once again.
The next part of the book, Hearts in Atlantis, takes place in 1966 and is narrated by Peter Riley, who has just started at the University of Maine. He has been a good student before, but he is drawn to the interminable card game of Hearts that is going on in the communal room in the all-male dormitory where he lives.
The story explores how the university of the 1960s was an "Atlantis", an imaginary kingdom isolated from the troubles of the world. However, as more and more of the students become addicted to playing Hearts, their grades begin to suffer...and the only way they are escaping the draft for the Vietnam War is through their student deferments. If they flunk out of college, they will be drafted and sent to the war in Southeast Asia.
Peter Riley quickly falls behind in his studies, but even though he knows he might flunk out, he is unable to stop himself. Meanwhile, he meets Carol Gerber, Bobby Garfield's friend and childhood sweetheart from Low Men in Yellow Coats. Peter Riley falls in love with her, and with her help tries to cure himself of the addiction to Hearts. However, he is too self-involved and therefore unaware that Carol herself has become caught up in an escapist addiction of her own: student terrorism. As Peter Riley and his friends' self-destructive addiction to Hearts continues, the Vietnam War grows closer, drawing Carol into an activist group and taking part in bloody demonstrations.
Blind Willie is about a Vietnam veteran's penance after the war. The main character in this story is Willie Shearman, and the story takes place over a single day in December 1983. At first we see him commuting from Connecticut to New York City like any normal businessman; we then discover that he elaborately disguises himself as a blind beggar who takes hundreds of dollars a day in donations from passersby, keeping the bills for himself and distributing the coins to various churches and charities. We also learn that he was in combat with John Sullivan, and saved his life; and that Willie keeps a scrapbook about Carol Gerber, and has never forgotten the day that she was beaten up by Harry Doolin while he and Richie O'Meara held her down.
Why We're in Vietnam describes a reunion of two veterans, one being John Sullivan, at the funeral of a third and recounts an incident that almost escalated into a My Lai Massacre involving a former student and player in the Hearts game in Hearts In Atlantis, Ronnie Malenfant. Throughout the story, Sullivan sees an old Vietnamese woman, "mama-san" whom Ronnie killed during this incident. In the end Sullivan dies of an apparent heart attack during a traffic jam on the way home.
In Heavenly Shades of Night are Falling, Bobby Garfield returns to his hometown after almost 40 years to attend John Sullivan's funeral, and finds closure to his relationships with Carol Gerber and Ted Brautigan.
Insofar as The Dark Tower Series' overall plot is concerned, it is revealed in the seventh book that Ted is essential to the Crimson King's quest to break the beams that hold the Dark Tower up, in turn, holding the universe together. Roses are repeatedly mentioned in the Dark Tower novels.
Carol's reference to a man teaching her how to be dim, and taking in "confused, angry kids," is an implied reference to Randall Flagg. The man's name - "Raymond Fiegler" - follows King's pattern of giving Flagg aliases with the initials "RF". The act of being dim is a trait shared by Flagg in Eyes of the Dragon.
When Bobby and Ted encounter a car and sense the low men that have been chasing Ted, Bobby describes feeling "his heart spin as a top did, with its lines rising and disappearing into other worlds. Other worlds than these." In The Gunslinger, Jake Chambers says "Go, then, there are other worlds than these" to Roland as he falls to his death. The two characters are also roughly the same age, and play similar adopted-son roles in their respective novels. This connection is further explored in the seventh Dark Tower novel.