Bart and Lisa go off for the summer to Krusty's camp for kids, but instead of meeting Krusty they meet his bean-counting surrogate, Mr. Black. With their children gone, Homer and Marge enjoy a romantic summer, but Bart and Lisa are put to work making crummy merchandise, until Krusty returns and sets things right-by taking the kids to Tijuana.
Marge wins the lead in a musical production of "A Streetcar Named Desire", in which Ned Flanders plays Stanley Kowalski. Marge is infuriated by Homer's brutishness and insensitivity during preproduction, until he sees the play and reveals to Marge that he has grasped its meaning. While rehearsing, Marge sticks Maggie in the Ayn Rand Day Care Center, where her pacifier is immediately taken from her, and a la "The Great Escape", she must struggle to win it back.
Homer decides not to attend church one Sunday and has the time of his life and vows never to return to church again, however one Sunday after falling asleep while smoking a cigar he accidentally sets fire to The Simpsons house, Flanders spots the flames and rescues him, Homer comes to his senses and turns up at church the following Sunday(asleep).
With her self-esteem shattered by a school carnival cartoonist, Homer decides to enter Lisa in a local children's beauty contest, which she ends up winning by default. But when she finds out how heavily involved Laramie Tobacco is in using the contest to sell cigarettes, she uses her position as a platform against the tobacco industry and other establishments of power and corruption.
In "Clown Without Pity", a Krusty the Clown doll goes berserk in the Simpson home. In "King Homer", Marge is wooed by a giant ape. And final story, In "Dial 'Z' for Zombies", Bart's attempt to bring back the family cat turns the town of Springfield into a pack of bloodthirsty zombies.
Homer buys a truck with an attached snow plow after he destroys his car, and to pay for it, he starts a snow shoveling business, calling himself Mr. Plow. It all goes off without a hitch, until he finds himself in competition with The Plow King, a.k.a. Barney Gumbel. Now begins the winter of discontent.
Years of poor eating habits catch up with Homer when he suffers a massive heart attack. The family can't afford the triple bypass operation he needs from Dr. Hibbert, so they go to a discount quack named Nick Riviera.
After receiving a considerable donation of money, the people of Springfield decide what to spend it on. Enter Lyle Langley, a jocular salesman who gets Springfield hooked on a monorail system. After the monorail is up and running, and with Homer as the conductor, it's time for the maiden voyage. Little do the people know they have just boarded a one-way train to Hell.
After Homer forgets to pick up Bart from soccer practice, Bart joins a mentor program called Big Brothers presenting himself as an orphan, and is assigned a big brother called Tom. When Homer finds out, he joins the program too as a big brother.
Feeling sorry for Ralph, Lisa sends him a Valentine card. Having developed a crush on her, Ralph invites Lisa to go see the Krusty the Clown show. She accepts but after Krusty asks them if they are boyfriend and girlfriend, Lisa lets Ralph know that she just wants them to be friends.
Homer plays a series of (childish) practical jokes on Bart. To get even, Bart uses a paint mixer at a local hardware store to shake up a can of Homer's beer. Homer opens the can, resulting in a huge explosion that seriously injures the Simpsons patriarch.