With help from a few Vanity Fair editors, this list was compiled by John Ortved, a contributing editorial associate at V.F. and the author of the August article “Simpson Family Values,” a behind-the-scenes oral history of the show. (For a more in-depth and democratic rating system, check out NoHomers.net, the unofficial home of all things Simpsons.)

All images © Fox.

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.