After Homer saves Mr. Burns from drowning, Mr. Burns rewards him with a dinner and a flight on his corporate jet. Enjoying the luxury and special features, Homer loves Mr. Burns's corporate jet so much he vows to never fly the regular way again, which prompts a pitying Marge to hire a personal life coach named Colby Kraus to help Homer achieve his dream of flying. However, when Homer is unable to get the job, he feigns going to work so his family would be proud of him.
After a freak accident, Homer lands in the hospital where Doctor Hibbert informs him he developed an ability to sing in an operatic voice, only when he's lying on his back. Mr. Burns immediately hires Homer to sing the leading role in his production of La bohème. Homer soon becomes an enormous celebrity, and after running away from a throng of crazed fans, Homer is saved by Julia, an obsessive and dangerous stalker who Homer is blackmailed to hire as his manager.
After touring neighboring town Guidopolis, Homer ends up having his car towed by a tow truck driver named Louie, who introduces Homer to the joy of towing cars for a living. However, after going "tow crazy", the residents of Springfield plot a revenge. Meanwhile, Marge begins to feel Maggie is getting too clingy and hires a counselor. The method works too well, leaving Maggie with no need for Marge at all, causing a depressed Marge to bond with a sack of potatoes.
"I Don't Wanna Know Why the Caged Bird Sings" (JABF19)
While waiting in line at the bank, Marge befriends a man named Dwight (Steve Buscemi), who later holds up the bank. Marge manages to convinces him to turn himself in, with the promise that she would visit him in prison if he does. Despite his turning himself in, Homer convinces Marge that Dwight will not expect her, so Marge, too frightened to go to prison, does not fulfill her promise and Dwight breaks out looking for her. After stalking her in various places, Dwight kidnaps Marge.
After remarrying, Kirk and Luann go on a honeymoon cruise; however, the boat tips, causing the two to topple into the sea and are later presumed dead. As such, Milhouse decides to act like a real man. As a result, his new attitude makes him more popular than ever, prompting to Bart decide to find a way to regain his popularity. Meanwhile, Homer finds himself in trouble when he can't remember the color of Marge's eyes, who vows never to show him her eyes until he remembers.
When a new comic book store, "Coolsville Comics & Toys" owned by a friendlier owner named Milo (Jack Black) opens up directly across the street from Comic Book Guy's store, Comic Book Guy competes for his customers. When he finally gives up, he sells the Android's Dungeon to Marge, who opens up her own women-only workout center called Shapes. Marge becomes rich and famous, which promps a self-conscious Homer to get stomach staples. Still feeling useless, he goes to get plastic surgery.
The Simpson family agrees to go to a rib restaurant advertisement, and after arriving, they discover Sideshow Bob attempts to murder the entire family. When Bob is captured by the police, he is put on trial, where Bart throws away his vial of medicine, inadvertently killing him. Bob's brother Cecil invites Bart to pay his last respects to Sideshow Bob. Although Bart doesn't know it, it turns out to be an elaborate plot devised by Bob's entire family to murder Bart instead. John Mahoney voices Dr. Robert Terwilliger, Sr., reuniting him with his Frasier co-stars Kelsey Grammer (Bob) and David Hyde Pierce (Cecil).
Homer wakes up in the snow with no memory from the night before, and Moe informs him he drank a "Forget-Me-Shot", a drink powerful enough to rid the previous 24 hours from a user's mind. With his family missing, Chief Wiggum and Ned Flanders tell him of a domestic disturbance from the night before, prompting Homer to worry he may have done something awful and tries to regain his memories with help from Professor Frink. After gaining portions of his memory, Homer believes Marge cheated on him.
Homer burns down Springfield's fast-food restaurants. In order to rebuild them, Mayor Quimby moves up election day, making Springfield's primary election the first in the nation. The candidates in the election are not compelling and voters instead write in "Ralph Wiggum" on the ballot and he wins. As a result, both candidates embrace Ralph, even though it is not known which party he is running for.
After discovering Marge's diploma, Homer recounts the story of how he gave up his dreams of being a musician so Marge could attend Springfield University. However, after she became attracted to one of her professors Homer started focusing his emotions into music and formed the first grunge band called Sadgasm. But after Homer's band breaks up, Marge must decide between a glum and miserable Homer and or her pretentious professor.
On Valentine's Day, the Simpson family gets stuck in a tunnel; to pass off time, Homer to begins to tell a romantic tale about Bonnie and Clyde, Marge tells her take on Lady and the Tramp, and Bart tells a tale about Sid and Nancy, where Nelson Muntz is Sid Vicious, Lisa is Nancy Spungen and Bart is Johnny Rotten from the Sex Pistols.
A new kid named Donny (Topher Grace) comes to Springfield Elementary and Bart thinks he's found the ultimate partner for pranks. However, these pranks backfire and Bart begins to suspect that there is a rat amongst his group of friends. Meanwhile, Marge wrecks the family car and Homer gets a new loaner vehicle, to which he becomes attached.
Homer goes on a diet, but cheats on it, and Marge hires a TV show to keep track of his diet and make sure he is being honest. Meanwhile, Bart and Lisa play a prank on Martin Prince which backfires, subsequently leading them to believe that they have killed him.
Lisa becomes a ballerina at an academy and discovers that her natural talent is enhanced by second hand cigarette smoke from the other dancers. Meanwhile, Homer reveals that he has secretly been making beef jerky and is dismayed when a family of raccoons steals it.
Lisa discovers that the town of Springfield hasn't collected millions of dollars worth of taxes. As a result, the town starts collecting from most of the evaders and the only remaining debtor is Lurleen Lumpkin (Beverly D'Angelo). As the police try to find her, Lurleen stays with the Simpson family. Lurleen is reunited with her father, however, he sells her song to the Dixie Chicks.
When Bart and Lisa save a cow, Lou, from going to the slaughterhouse, they give it to Mary, a farm girl (voiced by Zooey Deschanel). Her father mistakenly believes it as a token of marriage, prompting Homer and Marge to break the two up.
When Lisa creates a hit documentary about her family for a school project and enters it into the Sundance Film Festival, Homer, Bart and Marge become embarrassed by the candid behind-the-scenes look at their lives.
Homer's mom (Glenn Close) returns, and says her days of activism are over. But when she unexpectedly passes away, Homer feels guilty for not expressing his love for her before her death. He decides to fulfill her wishes by scattering her ashes over Lake Wastershare at Springfield Monument Park.
Lisa becomes Krusty the Clown's new assistant and steals his spotlight. She soon gets her own show and wins Entertainer of the Year at the Springfield Media Awards, but realizes that she may not be cut out for showbusiness after all. Meanwhile, Bart and Homer start coin-collecting.