The film opens with a scene that is repeated later in the film in which a reporter meets with police searching a cavern. He is told a game of Mazes and Monsters got out of hand.
Robbie Wheeling (Tom Hanks) starts college at the fictional Grant University and soon develops a group of friends, all of whom have their own personal problems and issues. Jay Jay (Chris Makepeace) feels marginalized by his mother, who constantly redecorates his room since she can't make up her mind about the best look. In his "self-decorating", he wears a variety of unusual hats. Kate (Wendy Crewson) has had a series of failed relationships, and suffers from her father leaving home; Daniel's (David Wallace) parents reject his dream of becoming a video-game designer; and Robbie's alcoholic mother and strict father fight constantly, and he is still tormented by the mysterious disappearance of his brother, Hall. They are fans of Mazes and Monsters, a fantasy role-playing game that had previously caused Robbie to get kicked out of his last school when he became too obsessed with it. Though he is reluctant, the other three students convince him to start playing again with them.
Through the course of playing the game, Robbie and Kate begin a serious relationship, in which he confides in her that he still has nightmares about his missing brother. Eventually, Jay Jay, upset by feeling left out by his friends, decides to commit suicide in a local cavern. In the process of planning it out, he changes his mind and decides the cavern would be better suited to a new Mazes and Monsters campaign. He dramatically kills off his character to force them to start a new campaign, in which he describes they will be living out their fantasy. He proposes playing his new game in a disused and condemned cavern, and dismisses the warnings from his friends – who reluctantly agree to participate.
During the actual spelunking, Robbie experiences a psychotic episode involving the last time he saw his brother, and he hallucinates that he has slain a monster, called a Gorvil. From this point forward, Robbie believes he is actually his character, the cleric Pardieu. This leads him to break off his relationship with Kate (to maintain celibacy), and to start drawing maps that will lead him to a sacred place he has seen in his dreams called the Great Hall. In his dream, the Great Hall tells him to go to the Two Towers, and he disappears.
His friends report him to the police while concealing their trip into the caverns. They and police investigators suspect he is deceased. Robbie travels to New York City, where he stabs a mugger whom he imagines to be a monster. He sees blood on his knife, then sees his bloodied clothes in a window and breaks out of his delusions for long enough to call Kate from a payphone. After he agrees to go to Jay Jay's house, a delusion leads him into the subway. Not finding him at Jay Jay's house, the friends deduce Robbie has equated the Two Towers with the Twin Towers of the World Trade Center. Robbie believes that by jumping off one of them and casting a spell, he will finally join the Great Hall. After a search, his friends find him and stop him from jumping off the south tower observation deck using the game's rules, once again pulling him out of his delusion.
The film ends with the friends visiting Robbie at his parents' estate, hoping to pick up their friendship where they left off. Though he is now in regular counseling, it is implied that Robbie will live out the rest of his life trapped in his imaginary world believing that he is still Pardieu, that his friends are really their characters, and that he is living at an inn (actually his parents' home) and paying for his boarding with a magic coin, which "magically" reappears in his pouch each morning. He then tells his shocked friends of a great evil lurking in the forest across the lake, believing that it threatens the lives of the "innkeeper" and his wife. The three, feeling sorry for Robbie and guilty for their role in his psychotic break, decide to engage him in a "game" of Mazes and Monsters, letting Robbie dictate the events to them. In the end, Kate says, "And so ... we played the game again ... for one last time."
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