Homer saves Mr Burns life once more and gets a free dinner as a result. Burns flies him to Chicago in his private jet. Home falls in love with the private jet and becomes depressed by the rest of his life. Marge hires a Life Coach to help him get what he wants in life. Homer goes for a job interview at a company where he will be able to fly their private jet. But when he doesn’t get the job he lies and says he did.

Homer hurts his back and while at the hospital discovers that while lying down he has a powerful singing voice. Mr Burns makes him the lead for the Springfield Opera House. Stardom has its pitfalls though as he and Marge are bothered by his fans. A mysterious woman, Julia, becomes president of Homer’s fan club. She tries to seduce him and when he rejects her she tries to kill him.

Homer is out looking for milk in Guidopolis when his car gets towed. He is so impressed by Louie’s towing lifestyle that he becomes one. He irritates the people of Springfield so much that they set him up to betray Louie who traps him in his basement. Meanwhile Marge is worried that Maggie is too clingy. She calls in help from C.R.I.E. who help Maggie become more independent. Maggie eventually tracks down Homer and rescues him.

Marge gets stuck at the bank during a robbery. She promises Dwight the robber (Steve Buscemi) that she will visit him in prison. But she can’t bring herself to do it. He escapes and forces her to take him to the theme park where his real mother abandoned him.

Three Halloween stories as usual. First is a Kang and Kodos story modelled on E.T. Next is a parody of Mr and Mrs Smith with Homer and Marge as the married assassins. Finally Bart, Lisa, Nelson and Millhouse cause terror in Springfield in Heck House.

The Van Houten’s get remarried and Milhouse is finally happy again. But they are lost at sea on their honeymoon and Milhouse is forced to toughen up to cope with the loss. He becomes the coolest kid in school and Bart tries to regain his popularity by contacting Milhouse’s uncle. Meanwhile Marge is shocked that Homer doesn’t know the colour of her eyes and won’t let him see them until he can remember.

A new comic book store puts the Androids Dungeon out of business. Marge then rents the space to open a gym for women. The gym is so successful that Homer starts to believe she will leave him for a more attractive man.

The Simpsons get Tivo. Marge feels guilty skipping the adverts and the family end up going to a new restaurant opening. There they discover it was all a trap by Sideshow Bob. His plan is foiled of course but during his trial he dies. Bart goes to pay his respects and Bob pops out of his casket and traps Bart in it. Lisa figures out Bob’s plan and leaves him and his family locked up in prison.

Homer comes home after a night of drinking to find no one is at home. He goes to Moe who tells him he gave him a special drink to forget. Thanks to Chief Wiggum and Grandpa, Homer goes to see Professor Frink. He helps Homer travel through his memories and discover most of what happened. But Homer thinks Marge cheated on him with Duff Man and tries to kill himself. But as he falls off a bridge he remembers what really happened and then he lands on a boat below where his surprise birthday party is taking place.

Homer’s greed leads to the destruction of Springfield’s fast food district. In order to raise money with a bond issue Mayor Quimby moves up election day. Springfield's primary election becomes the first in the country causing the media and candidates to descend on the city.

Homer didn’t pay the heating bill and as the heating gets fixed Marge and Homer tell the story of the 90s. The Simpsons’ back story is rewritten so that Marge goes to college and Homer pays for her tuition. She falls for her professor while Homer becomes the founder of grunge music. In the end they get back together and conceive Bart.

Marge and Homer get stuck on a carnival ride on Valentines Day. So they begin telling some of the great love stories: parodies of Bonnie and Clyde, Lady and the Tramp and Sid and Nancy.

Principal Skinner and Superintendent Chalmers bring in a new kid to be their inside man on Bart’s pranks. Bart discovers there is a rat in his gang and tries to find out who it is. Marge crashes Homer’s car and Homer becomes enamoured with the much nicer loaner car he is given.

Marge makes Homer start a new diet. When she thinks he is cheating on his diet, she calls a reality show called Sneakers to help her catch him. Bart and Lisa accidentally knock Martin Prince off a cliff and think they have killed him. Their guilt grows as Nelson (as Columbo) investigates.

Marge tries out for a ballet school but fails. So she pushes Lisa into trying to become a ballerina. Lisa finds the only way she can succeed is to join the other ballerinas in smoking. Homer gets Bart to help him with his beef jerky business. But racoons steal all the jerky. Homer uses the racoons to try and steal the ballerina’s cigarettes and manages to ruin their recital.

Springfield is broke. Lisa discovers that many people have unpaid back taxes owing. In the course of collecting them authorities discover that Lurleen Lumpkin owes a lot from her country music career but no one knows where she is. She appears in Homer’s car and moves in with the Simpsons. Marge discovers that her father abandoned her when she was young and goes out to find him. She does and Royce Lumpkin returns to her life. He then steals one of her songs and gives it to the Dixie Chicks. Marge helps Lurleen confront him and she gets her career back on track.

Bart joins the 4-H club. There he rears a cow called Lou with the help of farm hand Mary. Lisa helps him rescue Lou from being slaughtered and they take him to Mary’s farm to live in safety. But her father Cletus sees this as an a proposal and makes plans for the wedding. Marge switches Lou for Homer so that Bart doesn’t have to get married. Homer avoids being killed and Lou is sent to India.

Lisa makes a movie for film class and Principal Skinner encourages her to make a documentary about her family. She does and she enters it for the Sundance Film Festival. The family goes as do Skinner and Chalmers who produced the film. The festival loves it but the Simpsons family is reviled and Lisa feels guilty. They all get over it though when Nelson’s film steals the festival buzz the next day.

Homer’s mother returns but he refuses to believe that she won’t abandon him again. She dies and he feels terrible that he didn’t make peace with her. Her video will asks him to deposit her ashes from the highest point of Monument Park. When he does he realises she has sent him on one final protest.