Vanity Fair Pick Their Top Ten Simpsons Episodes

10. The President Wore Pearls (Season 15, 2003)



A parody of Andrew Lloyd Webber's Evita. Lisa replaces Martin as school president, beating Nelson in the election. The teachers, unhappy with the election result, turn Lisa's public against her by eliminating art, gym, and music classes. The final act (where the episode loses some steam) is an homage to the student strikes in Paris in 1968.

It may seem ludicrous to include anything later than Season 8 in this list, but this one is brilliant. The musical numbers are astoundingly good, and Lisa's comeuppance is so well constructed it harkens back to the golden years of the show (Seasons 3 through 8).

Great moment: The students are anxious about President Lisa's access to the teacher's lounge. "Is it true they make fun of students in there?" Milhouse asks. Lisa waves away this suggestion as preposterous, and opens the door to the lounge. Inside, Groundskeeper Willie is mocking Milhouse: "Look at me, I'm Milhouse. I tuck my T-shirt into me underpants. I have no friends, so I confide in Willie."


9. Krusty Gets Kancelled (Season 4, 1993)



When Krusty is pushed off the air by a new children's show starring a talking puppet, Bart and Lisa help Krusty arrange a star-studded comeback special featuring Bette Midler, Luke Perry, Johnny Carson, Hugh Hefner, and the Red Hot Chili Peppers. (Liz Taylor declines to participate.)

This is Krusty's best episode—better than the reunion with his father, or the Bar Mitzvah episode, which won an Emmy much later on. The incorporation of guest stars as themselves is top-notch, and we get to see the really dark side of Krusty's flailing showbiz career. Hollywood, television, celebrities, and fans are all beautifully skewered here.

Great moment: When Perry, who is Krusty's half-brother, pleads to be a part of the show, Krusty imagines shooting him from a cannon into a brick wall. Later, when Krusty actually does shoot him from a cannon, Perry flies through several buildings, including a sandpaper museum, shouting, "My face! My valuable face!," before landing in a pillow factory, which is then demolished.



8. Bart the Murderer (Season 3, 1991)


After a lousy day at school, Bart falls down some stairs and into the hangout of local mobsters, who give him an after-school bartending job. Principal Skinner disappears after causing problems for Bart at work; when the mobsters are put on trial for Principal Skinner's murder, Bart discovers there is no honor among thieves.

An oldie but a goodie. Here we're introduced to Fat Tony, voiced by Joe Mantegna, who is one of the most reliable recurring guest voices. This episode makes the cut because of the inspired Mafia satire (GoodFellas, The Godfather) and because it goes deeper into Bart's ongoing conflict with authority figures.



7. Homer's Enemy (Season 8, 1997)

Mr. Burns is touched by a news story about an unfortunate man named Frank Grimes, who suffered terrible hardships as a child but went on to earn a degree in nuclear physics. Mr. Burns hires him at the nuclear plant, where Homer's buffoonery and laziness earn Grimes's ire.

Perhaps the darkest Simpsons episode ever. Grimes works hard, is honest and unselfish; he is quite literally everything Homer is not. To see him fail, and ultimately be destroyed, once he enters Homer's world is hilarious and satisfying. Longtime scribe George Meyer once jokingly speculated in an interview that it was after this episode that the show lost its moral grounding.

Great moment: Homer: "Hi, Grimey, old buddy." Grimes: "I'm not your buddy, Simpson. I don't like you. In fact, I hate you! Stay the hell away from me, because from now on, we're enemies!" [Grimes turns to leave.] Homer: "O.K. Do I have to do anything?"



6. The Itchy & Scratchy & Poochie Show (Season 8, 1997)



When the producers of Itchy & Scratchy realize that viewers have become tired of the show, they introduce a new character, Poochie, a dog, voiced by Homer. Poochie, cobbled together by network executives, is resoundingly rejected by the public.

This episode, the 167th, marked the moment that The Simpsons surpassed The Flintstones as the longest-running animated sitcom ever. A classic satire of network influence, obsessed TV fans, and programs that survive long after the shark has been jumped, the episode is a meta-celebration, a tongue-in-cheek rebuttal to everyone who claimed that the quality of The Simpsons had declined over the years.

Great moment: After the ratings come in and the Itchy & Scratchy executives discover that everyone hates Poochie, Homer shares his ideas about how to improve the show: "One, Poochie needs to be louder, angrier, and have access to a time machine. Two, whenever Poochie's not on-screen, all the other characters should be asking 'Where's Poochie?' Three …"

Tidbit: George Meyer voices the writer who insults the network executives and mocks their corporate-speak. Also animated in that scene are show-runners Bill Oakley and Josh Weinstein. (Oakley is later roughed up by Krusty.)



5. Two Bad Neighbors (Season 7, 1996)



Homer goes to war with his new neighbor, George H. W. Bush. The former president steals Homer's title of "King of the Neighborhood," then spanks Bart after the unruly child destroys his memoirs (which conclude, "Since I've achieved all my goals as president in one term, there was no need for a second").

Conservatives ended up loving The Simpsons, because the show extolled the importance of family, church attendance, and distrust of institutions. But George H. W. Bush and his family-values cronies were originally against the show. Barbara Bush once called it "the dumbest thing I've ever seen." While the Simpsons people have always claimed evenhandedness in their satire, the show is, after all, hardly right-leaning, and it's hard to miss how gleefully the former president is mocked here.



Great moment: Marge finds a rhinestone jacket in the attic with the words disco stu printed on the back. Homer explains that he meant to write disco stud, but ran out of space. Later, at a garage sale, a dancer named Disco Stu refuses to buy the jacket, insisting that "Disco Stu doesn't advertise."



4. Cape Feare (Season 5, 1993)



After Sideshow Bob is paroled, the Simpsons go into the witness-protection program, becoming the Thompsons and moving to a houseboat on Terror Lake, where Sideshow Bob tracks them down. Bart is saved by H.M.S. Pinafore. This episode's masterful integration of filmic parody and a recurring character puts it near the top.

Great moment: Prosecutor: "What about that tattoo on your chest? Doesn't it say die bart die?" Sideshow Bob: "No, that's German [unveils tattoo] for the bart the." [courtroom murmurs in collective understanding.] Female parole-board member: "No one who speaks German could be an evil man."

3. Marge vs. the Monorail (Season 4, 1993)

A tribute to The Music Man, written by Conan O'Brien. A straw-hatted huckster blows into town and, using a catchy song-and-dance routine, manages to sell Springfield an unnecessary monorail of dubious safety. Homer becomes conductor.

An amazing musical number; Leonard Nimoy in a random guest appearance. What else could you want? Besides being replete with excellent jokes, this episode reveals the town's mob mentality and its collective lack of reason. This is the episode that defines Springfield more than any other.

Great moment: Homer is watching television. TV commercial: "Are you squandering the precious gift of life in front of the idiot box? Are you on your third beer of the evening?" Homer: "Does whiskey count as beer?"

2. Bart vs. Australia (Season 6, 1995)

Bart causes an international incident when he makes a collect call to an Australian household to see if the water in the Southern Hemisphere drains clockwise; the phone bill turns out to be astronomical. The Simpsons travel to Australia so Bart can make a public apology, but are betrayed by the State Department, which fails to inform them that Bart's punishment will also involve "a booting" (a kick in the rear end, with a boot).

Great moment: A Paul Hogan–ish man approaches Bart, who is playing with a penknife. Aussie: "You call that a knife? [thrusting out a spoon] This is a knife." Bart: "That's not a knife, that's a spoon." Aussie: [with admiration] "I can see you've played knifey-spooney before."

Tidbit: The family and staff fleeing the embassy is an allusion to the fall of Saigon.

1. Rosebud (Season 5, 1993)

A perfect episode. Mr. Burns's lamentations for his childhood bear, Bobo, lead to a show-long parody of Citizen Kane. (Maggie has the bear and refuses to give it up.) At once a satire and a tribute, the episode manages to both humanize Mr. Burns and delve deep into Homer's love for his oft-forgotten second daughter, Maggie. Also, the Ramones guest-star.

Great moment: Mr. Burns has tried to bribe Homer to get the bear, but Homer has resisted, for Maggie's sake. Here, he is trying to coax the bear away from Maggie.

Homer: Maggie, I know you like the bear, but wouldn't you be just as happy playing with … [looks around, then picks up a cardboard box] this box! [plays with it] See Maggie? See the fun box? Do-do-do-do-do-do!
Maggie reaches for the box.

Homer: No! My box! My box!
He runs to the other side of the room and plays by himself. Later, in the bedroom, Marge enters, her hair a mess.

Marge: Mmm, I think we need a new hair dryer.

Homer: Marge, you must hate me for not taking Mr. Burns's money.

Marge: I don't hate you, I'm proud of you! You came through for your daughter when she needed you the most.

Homer: Aw, thanks, Marge. But it'll take a lot more than that to comfort this tortured soul. [he picks up his box, and his mood changes immediately.] Hee boxy!

Marge: [snatching the box] Gimme that!

Homer: Awww …