We Asked Experts for 10 of Their Most Memorable Simpsons Episodes of All Time

Raisa Bruner

This week, The Simpsons celebrates its 30th anniversary of being on air. That’s three “D’oh-” and donut-filled decades of Homer’s mishaps alongside Marge, Bart, Lisa and Maggie as they scheme through the years in Springfield in brilliant cartoon color. The show has also picked up a collective 34 Primetime Emmy Awards over its expansive run, making it a critical hit too.

Despite the longevity of the series, none of the citizens of the Simpsons world have aged a day. But their comedy has grown up around us and become an indelible part of the American cultural landscape.

Sometimes, the show has seemed to tell the future. Other times, it has been a wry reflection of present and past.

Originally created as an offshoot of cartoon interludes on FOX’s Tracey Ullman Show by Matt Groening in 1987, it is developed by James L. Brooks, Matt Groening and Sam Simon.

To celebrate and consider the show’s hefty legacy, TIME spoke to three Simpsons scholars and experts who have written extensively about the show over the years, particularly about its lauded first decade. Journalist John Ortved, who wrote The Simpsons: An Uncensored, Unauthorized History, considers it one of our most powerful cultural forces in television. “I’d put The Simpsons right up there — I think it’s as or more powerful than Saturday Night Live,” he told TIME. Chris Turner, another journalist and author of Planet Simpson: How a Cartoon Masterpiece Defined a Generation, agrees. For Ray Richmond, critic and co-author of The Simpsons: A Complete Guide to Our Favorite Family, it’s one of the classics.

Most critics accept that the second half of the show’s run hasn’t hit its early subversive highs. But it still claims respect. “Even at its lowest, it’s been greater than almost every comedy,” Richmond says. The trick was that it took a traditional family sitcom and added the cartoon twist. “At its core it’s just a feel-good show about this wonderful family. It’s a combination of character development, great guest stars, sight gags and homages to the past and to films,” he explains of its longstanding appeal.” As for its future? “It will never go out.”

Here are ten of the most memorable of the show’s episodes according to those who have studied the iconic show over its run, focusing primarily on its acclaimed first 15 years.

10. “Rosebud,” Season 5, Episode 4. 1993.

This Citizen Kane homage gets into the backstory of Mr. Burns, recalling his beloved childhood teddy bear, Bobo, that he discarded in exchange for ascension to a life of wealth — and his lifelong quest to recover the treasured object. “It’s as perfect an episode of television as I’ve ever seen,” Ortved says. There are extensive historical references as Bobo’s journey is traced from Mr. Burns through the hands of Adolf Hitler and an expedition to the North Pole before miraculously ending up in the arms of Maggie, Homer’s daughter — leading, of course, to a Homer vs. Mr. Burns showdown. To top it off, there’s voice acting from the Ramones (yes, the rock star Ramones), adding an official layer of punk rock cool to the show. “On some level The Simpsons is a kind of punk rock TV show, or certainly was,” Ortved says. That irreverence has only enabled its long life.

9. “Cape Feare,” Season 5, Episode 2. 1993.

This is what Richmond calls the “ultimate Sideshow Bob episode.” It’s primarily a play on the Oscar-nominated 1991 movie Cape Fear, a psychological thriller from Martin Scorsese. In the Simpsons version, Homer and his family are terrorized by Homer’s nemesis Sideshow Bob, voiced by actor Kelsey Grammer; they end up entering the witness protection program and relocating to a new town and a houseboat to try to escape. But despite the dire context, they’re still able to mine plenty of comedy out of the circumstances. One of the most memorable parts of the episode is a comic bit that’s become Simpsons legend: Sideshow Bob keeps stepping onto rakes that continually whack him in the face. “It was one of those things where they were almost testing the theory that anything repeated enough becomes funny,” Turner says. “It becomes kind of repetitive and tedious, but by the seventh or eighth time it’s funny. It’s a comedic exercise.” And it worked.

8. “Homer’s Enemy,” Season 8, Episode 23. 1997.

This episode explores what happens when reality — or something like it — bumps up agains the Simpsons fantasy. In it, Mr. Burns hires a hard-working man named Frank Grimes to join the power plant. But when Grimes is stuck with Homer, he is driven to madness and, ultimately, death. “It’s quite dark,” admits Ortved, “but you and I laugh so hard, because you realize everyone in the Simpsons world has become so inured to Homer’s stupidity, gluttony and downright parasitic laziness. And you realize that these people have become not only OK with it, but charmed by it — and so have you.” Ortved calls it the “Hannah Arendt episode” for its wry portrayal of the banality of evil — a timeless term originally coined by the German-American theorist following the Holocaust. “Homer’s Enemy” also has its share of critics who see it as a bit too on the nose in its unusually clear-eyed depiction of Homer’s faults, making it one of the show’s more controversial episodes.

7. “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer),” Season 8, Episode 9. 1997.

In this foray into a newly surrealist realm — or a “spirit quest acid trip,” as Turner describes it — Homer wins a hot-pepper-eating contest only to start hallucinating due to the strength of the peppers. While on his metaphysical journey, strange things happen; he shatters the sun, for instance. (“It’s one of the few old-school cartoon things they did in the show,” Turner recalls.) He also encounters a coyote spirit guide, voiced by country icon Johnny Cash. Ultimately, Homer’s quest leads him to question his relationship with Marge — but by the end of the episode, he has seen the light and re-confirmed Marge as his soulmate, a touching moment of romance in a show not always best known for its sensitivity to love. The unusual visuals in the animations make it particularly memorable in the show’s run.

6. “Deep Space Homer,” Season 5, Episode 15. 1993.

In this take on 2001: A Space Odyssey, Homer heads to the cosmos after being selected as an average-Joe astronaut to give NASA better ratings. In typical Homer fashion, he manages to mess up the navigational instruments with a smuggled bag of chips and unleashes an ant farm upon the shuttle, which he erroneously ends up believing are giant, alien ants. Predictably, mayhem and near-death mishaps ensue, although Homer is safely returned to earth. Memorably, astronaut Buzz Aldrin and rock star James Taylor make voice cameos. And as for the jokes? “It’s still got some of my favorite single lines in the show,” Turner says, and Richmond concurs that he’s still got a soft spot for the episode.

5. “Homer at the Bat,” Season 3, Episode 17. 1992.

In order to win a softball game, Mr. Burns hires major league baseball stars to staff up the company’s team. Notably, the Simpsons team managed to get the actual celebrities themselves to voice act their characters, from Roger Clemens to Ken Griffey Jr. “It’s amazing in retrospect that they managed to get these celebrity athletes,” explains Turner. “But the episode isn’t in thrall to whoever it is. It’s really held up.” Thanks to the nine players who contributed, it’s an iconic episode that showcases the power of the Simpsons‘s allure to draw in unusual cameos.

4. “The President Wore Pearls,” Season 15, Episode 3. 2003.

Clever, precocious Lisa becomes student body president of Fairfield Elementary School in this episode that parodies the opera Evita, with Lisa even singing a spin on “Don’t Cry For Me, Argentina” as she goes on to rule the school. “It’s a really careful and smart satire and tribute to a musical, a great exploration of Lisa,” Ortved explains, “and it gets into a character’s weakness and darker sides — and her hunger for power.” Beyond that, the episode is full of small jokes and gags that keep it memorable, including a cameo from filmmaker Michael Moore as himself. “It’s highly watchable, the songs are good, the pacing is great, and it has these wonderful moments that explore the tension between kids and adults,” he says. For instance, there’s a point at which Lisa, as president, has access to the teacher’s lounge. Awed by her power, the other students suggest the teachers must make fun of the kids in their private chamber. And sure enough, when Lisa peeks in on the teachers, she discovers Willie the groundskeeper making fun of the students — a cutting commentary on the cruelty of adults, as explored by a child. “There’s no single episode after that that holds up as well,” Ortved says.

3. “Treehouse of Horror V,” Season 6, Episode 6. 1994.

In their fifth installment of the annual — and much-loved — Halloween-themed “Treehouse of Horror” episode, the Simpsons creators parodied a number of famous scary stories to sharp comic effect. “The Shining,” which is the segment that’s most well-remembered, sees the family get hired by Mr. Burns to take care of his mansion. Homer quickly deteriorates under the circumstances, to murderous effect. Richmond says the Halloween episodes are “always a great highlight,” but this one stands out for the specificity of its homages — and the quality of the animation, for which The Simpsons doesn’t always get a lot of credit, but which improved by the time this episode came around. Turner agrees, calling the 3D animation a “huge deal at the time.” Besides its play on The Shining, there’s also an homage to the musical Sweeney Todd involving the students in the school cafeteria that delights in the macabre.

2. “The Itchy & Scratchy & Poochie Show,” Season 8, Episode 14. 1997

In this self-skewering episode, a popular kids’ show in the Simpsons’s universe — The Itchy & Scratchy Show — decides to make an attempt to inject fresh energy into its world with the addition of a new character, Poochie, to keep the attention of the audience. The show was not afraid to take a mirror to itself, with this episode as proof. “The Simpsons has always been good about tracing their own line, and commenting on their own success and their own failures,” Ortved notes. “The fact is, you can’t be that funny for that long, and comedy moves on. It’s a brilliant comment and takedown of popular television,” he says. “It’s both prescient and really critical.” Turner agrees: “It’s a satire of the show itself in a lot of ways. The discussion that leads to the invention of Poochie has to be the most cited criticism of bad TV writing.” At the end of the episode, the character of Poochie is summarily dispatched — a cautionary tale of how quick fixes to grab more eyeballs are not a true solution for waning attention in the entertainment industry.

1. “Marge vs. the Monorail,” Season 4, Episode 12. 1993.

In one of the show’s finest homages to classic theater, a traveling salesman named Lyle Lanley, voiced memorably by Phil Hartman, comes to Springfield and sells the town on the concept of a monorail, á la the musical The Music Man. The townspeople are quick to fall for his song-and-dance routine, and naturally Homer ends up as the conductor of the faulty — and highly unnecessary — new form of transportation. Written by Conan O’Brien, it’s a fast-paced, joke-filled episode that turns The Simpsons from a quirky sitcom into a surreal social critique.

“The voice of reason is completely thrown out the window for something quite funny and fun and imaginative,” explains Ortved, identifying the reason this episode stands out: “The Simpsons have always kept this kind of Aristotelian unity; they only did stuff that could happen in the real world, despite the fact they were a cartoon. And then all the sudden you have this whole thing that explores the imaginative possibilities of animation and the elasticity of the characters. The writers had to make their reaction to something this big make sense, which is a tribute to them.” From the musical numbers to a cameo from the legendary Leonard Nimoy (who plays himself, but with his role referencing Mr. Spock) to the comic spin on dangerous group psychology, it’s an eminently thoughtful episode that has stood up over time.

To stream some of the best episodes of The Simpsons included here, FXX kicks off a 15-day long marathon of 661 episodes of The Simpsons from the first 30 seasons starting Tuesday.