- "This is not good. Definitely not good."
- —Richard Tyler's catchphrase
- "Good. That was definitely good."
- —Richard's new catchphrase when he makes the courageous new jump across the bike ramp.
Richard Tyler is the shy, later courageous, hero from "The Pagemaster". This is Macaulay Culkin's first and only G-rated role, as he portrayed both his live-action form and his voice in animated form. Richard is a young pessimistic boy who is panphobic (fearing just about everything), and lives his life based on statistics. His exasperated parents (Ed Begley, Jr. and Mel Harris) have tried multiple ways to build up the courage of their son, but to little success. Richard is sent by his father to buy a bag of nails so that he can build a treehouse. However, Richard gets caught in a harsh thunderstorm and takes shelter in a library. Here, he is met by Mr. Dewey (Christopher Lloyd), an eccentric librarian who tries to find a book for Richard and gives him a library card. However, Richard does not want any books; he just wants to call his parents and go home. Mr. Dewey points the boy towards a payphone. Richard wanders off and finds a large rotunda painted with classic fictional characters. Richard slips on some water that had dripped from his coat and falls down, hitting his head and knocking him unconscious. He awakens and finds the rotunda paintings melting, forming a wave of color that transforms him and the library into illustrations.
Richard is approached by the Pagemaster who sends him on a journey into the fiction section to find the "exit". Along the way, Richard befriends three anthropomorphic books: Adventure (Patrick Stewart), a swashbuckling pirate-like book; Fantasy (Whoopi Goldberg), a sassy but caring fairy tale book; and Horror (Frank Welker), a fearful "hunchbook" with a misshapen spine. The three agree to help Richard to find his way out if he checks them out with his library card. Together, the quartet encounter classic-fictional characters. They meet Dr. Jekyll (Leonard Nimoy) in a haunted house where he then turns into Mr. Hyde and terrorizes the group, driving them to the roof where they then head out into open waters to the Land of Adventure. However, the group are separated after an attack by Moby Dick. Richard and Adventure are picked up by the crew of the Hispaniola, captained by Long John Silver (Jim Cummings). The pirates go to Treasure Island, but find no treasure, nearly causing a mutiny between the captain and crew. Fantasy and Horror appear and defeat the pirates. Silver attempts to take Richard with him, but he retreats when Richard threatens him with a sword. Adventure insults Horror, causing the hunchbook to get captured by Lilliputians from Gulliver's Travels. Adventure saves him and they make up.
As the group travels through the fantasy section, Richard sees the exit sign on the top of a mountain. However, a sleeping dragon is awakened and chases Richard and his friends. Richard fights the dragon off with a sword and shield, but the dragon wraps its tail around him, shaking his armor and weapons off of him before swallowing him whole. Richard finds books in the dragon's stomach and uses a beanstalk to escape, he then jumps and the Dragon bites the beanstalk defeating him. The heroes arrive at the top and enter a large dark room where the Pagemaster awaits them. Richard berates the Pagemaster for the horrors he has suffered, but the Pagemaster reveals that the journey was intended to make Richard face his fears. Dr. Jekyll, Captain Ahab, Long John Silver, and the dragon reappear in a magical twister congratulating him. Richard then awakens, discovering that he had been "unconscious" all along. Adventure, Fantasy, and Horror all appear next to his body as real books. Mr. Dewey finds him, and, even though the library policy only allows a person to check out two books at time, lets him check out all three books "just this once" as Richard may not have been unconscious and may actually have witnessed all the events that happened, thus making Mr. Dewey the Pagemaster. Richard returns home a braver kid, sleeping in his new treehouse. Adventure, Fantasy, and Horror appear as silhouettes on a wall talking.