Homer's Enemy
In a new segment of "Kent's People", Kent Brockman tells the heartwarming story of Frank Grimes, a man who had to struggle for everything he ever got, including a correspondence degree in nuclear physics. After seeing the show, Springfield Nuclear Power Plant owner Mr. Burns is so happy that he asks Smithers to hire Grimes as his Executive Vice President. However, the following day, Burns sees a sentimental story concerning a heroic dog and demands that it instead be appointed Executive Vice President. Consequently, Grimes is shuffled into Sector 7G, where he must work alongside Homer, Lenny, and Carl. Settling into his new job, Grimes is amazed and aghast at Homer's bad manners and general irresponsibility. When Grimes prevents Homer from drinking a beaker of sulfuric acid, dramatically slapping it out of Homer's hands into a wall, a passing Mr. Burns admonishes Grimes for destroying the wall and spilling his acid. Grimes is demoted and later angrily declares to Homer that the two of them are now enemies.

Homer attempts to appease Grimes by inviting him to his home for a lobster dinner in order to make him and his enemy co-worker a friend. Grimes' visit to the Simpson house only fuels his resentment; he is incensed by Homer's ability to live such a comfortable life despite his slothful and ignorant ways. Declaring Homer a "fraud", a bitter Grimes storms away in anger. The following day, Homer, after getting advice from Marge, makes further attempts to earn Grimes' respect by acting as a model employee, but his efforts fail. Grimes rants about Homer to Lenny and Carl, both of whom insist that Homer is an essentially decent person. To prove Homer's lack of intelligence, he tricks Homer into entering a nuclear power plant design contest intended for children, by carefully cutting away all references to them in a promotional poster which he leaves at Homer's control panel. Homer, unaware that the contest is only open to kids, eagerly takes on the challenge to prove his professionalism. At the contest, Grimes is shocked when Homer's model, which is almost exactly the same as the current power plant with only a few modifications, easily wins against Ralph Wiggum's Malibu Stacy dream house, and Martin Prince's futuristic model that supplies power to the room. The audience's applause and cheers for Homer cause Grimes to finally snap and he runs amok through the plant, mimicking Homer's habits. Entering Homer's office, Grimes sees a machine labeled "Extremely High Voltage", sarcastically declares that he does not need safety gloves, grabs the high voltage wires and is killed by electrocution. At Grimes' funeral, Homer falls asleep and in a drowsy state tells Marge to change the TV channel, causing all the attending mourners to laugh as Grimes' casket is lowered into the ground.

Meanwhile, Bart becomes bored during a visit to Springfield Town Hall and buys "35 Industry Way" for a dollar during a foreclosure auction. It turns out to be a run-down old factory, which he and Milhouse spend the day wrecking it until the next morning Bart returns to find it has collapsed during the night while Milhouse was on watch duty, leaving the rats to swarm Moe's Tavern.

Bart the Fink
After the death of great aunt Hortense, the Simpson family attends a will reading. Each member of the family discovers they will receive $100 to do with as they like, but only after spending the night in a haunted house (which is surprisingly pleasant). Though Bart wishes to buy a hundred tacos from the TacoMat and Lisa to contribute to the Corporation for Public Broadcasting, Marge has them open bank accounts at the Bank of Springfield. Bart is excited with his new checking account, and begins writing checks for his friends.

Bart attempts to get Krusty the Clown's autograph, but Krusty is having a new sandwich named after him and has to leave. Just before he does, Bart slips a check for twenty-five cents into Krusty's pocket, figuring that he will receive a copy of it endorsed with Krusty's signature with his monthly bank statement. However, when Bart receives the check, it is endorsed with a stamp ("Cayman Islands Off-Shore Holding Corporation") instead of a signature; dismayed, Bart takes the check back to the bank so that they can force Krusty to sign it. The bank teller informs Bart that stamping the back of a check is perfectly legal, but becomes suspicious after analyzing the stamp and excuses himself to make a phone call. Five minutes later, Krusty is arrested for tax evasion, though Bart is not made aware of this for several hours.

The IRS takes control of Krusty's assets and his show (renaming it Herschel Krustofsky's Clown-Related Entertainment Show and turning Krusty Burger into IRS Burger, with meals named with tax-related terms and a six-to-eight-week wait to the customers, who apparently must report their income with every order as Homer asked Marge how much she lost on gambling), reducing his lifestyle to that of an average citizen. One evening, as the town watches, a depressed Krusty pilots his airplane into a mountainside. He is later pronounced dead.

A memorial service is held for Krusty at which Bob Newhart offers condolences. While everyone assumes that Krusty is dead, Bart believes otherwise when he begins to see a Krusty look-alike all over town. With Lisa's help, he soon discovers that Krusty has gone into hiding under the disguise of Rory B. Bellows, a grizzled old longshore worker. With Krusty leaving on a boat heading for the ocean, they supposedly convince him to return to his former life. However, Krusty had insured the life of his pseudonym and rigged his boat with explosives; returning to shore with Bart and Lisa, "Bellows"'s boat explodes, allowing Krusty to collect the insurance cash and end his tax woes.

I watched Bart the Fink the other night in prep for this matchup, and it's funnier than I remember. And Homer's Enemy is sort of dark and upsetting.

Homer's Enemy is a classic. I love how brutally dark the ending is.