While on a family trip to Shelbyville, Marge is dismayed to see how Springfield residents are perceived as hicks in a production of "Song of Shelbyville." At the next Springfield Cultural Activities Board meeting, Marge convinces the townspeople to fund a Frank Gehry designed concert hall, which goes bankrupt opening night. The ever generous Mr. Burns assumes the debt of the hall and turns it into The Montgomery Burns State Prison. When Mr. Burns pressures Chief Wiggum to increase capacity from 99% to 100% Homer finds himself imprisoned for kicking a can down the street 5 times in a row. Homer becomes a snitch after accidentally ratting on Snake during a breakout. Homer enjoys the benefits of snitch life until Fat Tony puts a mark on his head for selling out the mob. As president of the Activities Board, Marge uses her concert hall key to sneak into the prison and convince Homer that snitching is wrong. National Guardsman swoop in at the last moment to save the cornered couple and Homer decides to use his snitch powers for good by having the prison shutdown.
Professor Frink uses an astrology machine to show Bart and Lisa what their last days as high school students will be like if they dont mend their ways. In the not-so-distant future, robots are a part of life, Moe has a clone, Homer and Marge are separated, Lisa is dating a muscle-bound Milhouse and Bart is dating the girl of his dreams, Jenda. Bart and Jenda sneak away to an abandoned Frinks house where Bart uses the astrology machine to peer further into the future. Bart is dismayed to see an unhappily married Lisa and Milhouse caring for geriatric versions of Homer and Kirk. Barts conscience causes him to leave Jenda, stop Milhouses advances and return the Yale scholarship from Mr. Burns to his sister. In the present, Bart and Lisa see how the selfless act reunites Homer and Marge.
Don't Fear the Roofer
The perfect storm hits Springfield causing the Simpson roof to leak. Marge doesn't approve of Homer's "Hot Wheels" gutter system and questions what type of father can't keep a roof over his family's head. A downtrodden Homer seeks companionship at Moe's, however, he is quickly driven away for accidentally announcing Lenny's surprise party. Homer's last option is Knockers, a Hooters-style bar, where he befriends a beer and Curly-Joe-Derita-loving roofer, Ray (voiced by Ray Romano.) Ray and Homer attempt to repair the roof while Marge and the kids visit the Retirement Castle. Ray never shows and just before Dr. Hibbert drugs him with a syringe, Marge sweetly tells Homer that Ray is a figment of his imagination. Homer awakes in a mental hospital to "Fight Club"-styled testimonials from Bart, Ned and the Knockers' bartender (all people who allegedly saw Ray) that confirm the initial diagnosis. After a round of electric shock treatment, a cured Homer and family see Ray in the hospital lobby who explains the errors in the previous testimonials. An outraged Homer finds reparations as he and Ray sit on lawn chairs drinking beers while a malpractice shy Dr. Hibbert fixes the roof.
The Heartbroke Kid
When new vending machines are installed in Springfield Elementary, Bart quickly becomes a junk food junkie. Barts steady diet of processed foods shockingly leads to a massive weight gain and ultimately a heart attack. He is then put on a strict diet, but is unable to adhere to it. The Simpsons perform an intervention and he is shipped off to Serenity Ranch. He cheats on his diet there as well, until he finds out that his family has turned their home into a hostel working day and night to please demanding and unfriendly foreigners to pay for his stay at Serenity Ranch. In the end, Bart smashes the vending machine that made him fat in the first place and gives the money to his family.
A Star Is Torn
Aside from Lisa, everyone in the family contracts food poisoning after eating organic produce from a farmers market. After nurturing the family back to health, Lisa agrees to participate in a Krusty sponsored "Lil Starmaker" competition, with the first-prize winner being animated into an "Itchy and Scratchy" episode. Lisa panics during the competition when a girl (Fantasia) performs a better rendition of "Mocking Bird," and Homer saves the day by hammering out a manipulative tune about Springfield that leads Lisa to victory. With a win under his belt, Homer becomes a stereotypical star-crazed parent and manager who ultimately drives Lisa to fire him. A distraught Homer counters by taking Lisas rival, Cameron, under his wing and grooming him for the finals. Lisa comes to realize that her relationship with Homer is more important than the competition and performs an apologetic song. Homer reunites with his daughter before Cameron performs an egotistical song Homer prepared to sabotage the young boys performance.