After Homer saves Mr. Burns from drowning in a mall fountain, Burns thanks him by taking him on a whirlwind trip to Chicago on his private plane. Homer is smitten with the luxury jet and all the perks that come with it, including flying with song legend Lionel Richie, who serenades him with a customized version of "Say You, Say Me." After returning home, Homer makes it his mission to find a job that offers him the chance to fly on a corporate jet and enlists a life coach, guest star Stephen Colbert, to help fulfill this dream.
"Homer of Seville"
Homer injures himself in a fall, and while in the hospital he develops the ability to sing in a beautiful, operatic voice whenever he is lying on his back. Mr. Burns overhears Homer during one of his singing sessions at the hospital and immediately hires him to sing the lead in his production of La Bohme. Although Homer has to lie down during the performance, he wows the crowd at the Springfield Opera House. Homer becomes an enormous celebrity, especially with the ladies; much to Marge's chagrin. While running from a mob of crazed fans, Homer is saved by a mysterious woman named Julia (Maya Rudolph), who turns out to be a little too concerned for Homer's wellbeing.
Feeling that Maggie is getting too clingy, Marge hires a counselor to teach her the "C.R.I.E. Method," a counseling program that helps parents raise their children to be very independent at an early age. But the method works a little too well, leaving Maggie with no need for Marge at all. Meanwhile, Homer goes in search of milk for Maggie in Mookington and ends up having his car towed by a tow truck driver named Louie (Matt Dillon) who introduces Homer to the joy of towing cars for a living. Louie invites Homer to be the tow truck driver for Springfield on one condition: that Homer stay off of Louie's turf in Mookington. When Homer gets a little too "tow happy," the residents of Springfield set Homer up to look like he's towing in Louie's territory, and Homer must suffer the wrath. With Homer missing, the newly independent Maggie is spurred to action.
"I Don’t Wanna Know Why the Caged Bird Sings"
While waiting in line at the bank, Marge strikes up a conversation with a strange man named Dwight (Steve Buscemi) who later attempts to rob the bank. When the police show up, Marge convinces a cornered Dwight to turn himself in by promising to visit him in prison. As Dwight eagerly awaits Marge’s visit, Homer assures her that Dwight will not expect her to actually visit. But when Dwight receives a phone call and the caller (Ted Nugent) isn’t Marge, he escapes to find her. Watching the news report about Dwight’s jail break, she wishes she had kept her promise.
"Treehouse of Horror XVIII"
The frightfest begins in "Mr. and Mrs. Simpson"” as Homer and Marge leave for what appears to be an ordinary day. But Homer is living a double life as a secret agent, and he is assigned to eliminate Kent Brockman. When a mysterious woman blocks Homer’s shot and tries to kill Brockman herself, Homer finds that his competition "hits" a little too close to home. In "E.T. Go Home," Bart and Lisa come to the aid of Kodo the space alien, who’s hiding from the government. Kodo asks them to help him obtain a long list of devices so he can reconnect with his home planet, but his intentions prove to be anything but friendly. In the final Halloween scare, "Heck House," Bart, Lisa and their friends spend Halloween night pulling pranks on unsuspecting people in Springfield. But when they go too far, Flanders decides he’s going to spook them straight. Transforming the church into the "Heck House," Flanders is filled with supernatural power and subjects the children to his wrath of seven deadly sins.
"Little Orphan Millie"
When Milhouse's parents are lost at sea and presumed dead, Milhouse decides it's time to begin acting like a real man, and his new attitude makes him more attractive and popular than ever. Bart can't stand that Milhouse has become cooler than him, and he devises a plan to win back his cooler-than-Milhouse status. Meanwhile, Homer finds himself in hot water when he can't remember the color of Marge's eyes, and Marge vows not to let Homer see her eyes again until he remembers their color.
"Husbands and Knives"
Much to the Comic Book Guy's chagrin, Bart, Lisa and Milhouse check out a new comic book store called Coolsville, where they are treated like royalty by a friendly comic book buff named Milo (guest voice Jack Black). Coolsville attracts some real-life comic book creators, such as Alan Moore, Art Spiegelman and Dan Clowes (guest-voicing as themselves), and the Comic Book Guy wages war on Coolsville in an attempt to win back his customers. Meanwhile, Marge decides her middle-aged physique could use some help, and she launches a gym for "regular women." Marge's gym becomes wildly successful and as her fame grows, Homer fears she will dump him for a younger, more fit guy. Homer decides to take matters into his own hands to get into shape.
"Funeral for a Fiend"
Kelsey Grammer returns to guest-voice as the infamous Sideshow Bob, David Hyde Pierce as Sideshow Bob's dubious brother Cecil Terwilliger, and John Mahoney as their father, Mr. Terwilliger. Marge dreams that Keith Olbermann (guest-voicing as himself) chides her for fast-forwarding through television commercials. Marge tries her to make restitution by watching hours of advertisements, and she and the Simpson family take particular interest in an ad for Wes Doobner's World-Famous Family-Style Rib Huts. They drive to the restaurant, only to find Sideshow Bob waiting for them, triumphant in his elaborate hoax to lure them to their doom. When Sideshow Bob's attempt to terminate the family is foiled, he is put on trial, where his father blames Sideshow Bob’s psychosis on Bart. During the proceedings, Bart accidentally kills his old nemesis, and Bob's brother Cecil invites Bart to attend the memorial service for Sideshow Bob to bury the hatchet for good.