The Simpson family visit R. Bradbury's Traveling Night Circus and Lisa expressed her disappointment at being taken there, as she dislikes them and having three of them shutdowns in the past months. However, Lisa discovers the Illustrated Man where the manager fired him, a man with tattoos that transport individuals to alternate realities. Thus, the first story starts as the Illustrated Man shows the first tattoo to Lisa.

Bart heard noise from a woman screaming from beneath the earth in the woods. He runs home to get help, but Homer and Marge don't believe him, recalls that he previously claimed there was a boy in the woods crying wolf, yet they only found a large wolf upon investigation and no boy. Bart calls Milhouse with a tin can telephone to ask for help, but Milhouse is at his grandma's house and is unable to help. Consequently, Bart starts searching for missing woman every house and arrives at the Van Houten's home. There, Luann welcomes him and listen to his story, but she offers him excessive amount of milk, causing him to sleep.

However, Bart wakes up by stabbing himself with a sugar pixie stick and goes back to the grave, where he heard from a woman singing. He runs back home to inform Homer about this, who recognizes the song as one that Kirk used to sing a Double Beef Burger. They proceed to the grave and excavate it. The police arrested Luann for burying him alive for allowing Ms. Hoover to witness him purchasing her hair dye. Therefore, Wiggum releases her, citing that a murder in the 1950s is considered more acceptable than divorce. Marge assures him without doubt him again, and he informs them that Lisa is a communist, which leads Wiggum to take her away.

Back at the circus, the first story finished, and the second story begins, initiated by a tattoo of cogs. In the future, Chalmers finds himself in Skinner's office, where he soon becomes tired of its dullness. To relieve his stress, he visits Moe's, where Carl proposes a solution to his dilemma: a new technology involving a robot that resembles a human which he utilizes to evade interacting with Lenny. Chalmers gives a call to the "Marionettes Frinkorporated" company to place an order. Upon unboxing, the machine powers on itself as Chalmers stated, and takes them to the school. However, upon returning to the street, he finds Skinner there as well and chasing after him.

Getting tired, Skinner tells Chalmers that he purchased a robot as well to avoid being around him due to his mean manner. Soon, Carl finds them and instructs them to destroy the robot before it's too late, as it has become sentient and is experiencing emotions. He refuses to allow the original to go to Niagara Falls to enjoy time with Lenny, resorting to violence, which forces him to kill the robot. Chalmers and Skinner head to the school quickly, but they're too late; the robots have already forged friendships, and the children are now addressing their teachers by their first names.

Skinner kills his robot but accidentally kills the real Chalmers since he couldn't tell him and the robot apart. He is horrified by what he had done and holds the dying Chalmers who forgives him but soon befriends the robot Chalmers.

In the distant future, Homer is part of an arsonist organization called "Springfield Firehouse" specialized in burning all entertainment videos. While breaking in to arrest Groundskeeper Willie, he himself becomes interested in a funny video about a goat biting a farmer in the crotch. Willie convinces Homer not to burn the tape and even gives it to him to watch in secret before being arrested. However, Bart catches Homer watching the tape in the attic and rats him out.

The Springfield Firehouse break in to arrest Homer for breaking their rules by watching an entertainment video, but Homer escapes after switching clothes with Barney. He finds the Resistance hiding in a secret passageway behind Comic Book Guy's store, but the Firehouse break in and burn everything inside, having followed Homer. Homer escapes with the fugitives while the arsonists are distracted burning everything.

Lisa tries to leave after hearing all the stories, only to realize she herself has somehow become one of the Illustrated Man's arm tattoos. She panics and begs to be let out, but the Illustrated Man assures her she'll make friends with the other tattoos. Lisa tries to befriend the sun tattoo, only to panic again when the sun tattoo starts singing "Santaria" by Sublime.