If you weren’t a kid in the 80’s or 90’s you may find the following crazy: The Simpsons, in it’s prime, was the greatest television show of all-time. That prime has come and gone and pretty much ceased before the beginning of the millennium, but when the show was firing on all cylinders it was impossible to beat. Because of it’s amazing core of young writers, which included Conan O’Brien, it was hilarious and socially relevant; two things that you can’t say about the show today. So, with that, we at BabbleTop had the horrible task of finding the Top 15 episodes of all-time, all of which occurred between seasons three and nine.
15. Lemon of Troy
The Lemon of Troy is one of those episodes that shows why The Simpsons is such a great show. Few shows have had such a diverse range of characters, not in regards to skin color (since they’re all mostly yellow) but in regard to which character or characters they’ll follow in a given episode. Seinfeld, for example, always focuses on one of the four main characters whereas The Simpsons can focus on the main family, their friends or even their enemies. Lemon of Troy focuses on Bart and his friends as they enter the Bizarro-Springfield to essentially fight Bizarro-versions of themselves (and to get their beloved lemon tree back). While it is pretty similar to a Seinfeld episode, it’s one of the great episodes in the show’s history because it builds upon the history of the town of Springfield and it’s rival, Shelbyville. For anyone who grew up in a town with a rival (which is most of us), it’s hilarious to see the kids get freaked out by yellow fire hydrants or watch them hate another group of kids for acting too much like them: “He said radical, I say radical! I feel like I’m gonna explode!”. The jokes here are on another level and show that when The Simpsons was firing on all cylinders it was hard to beat.
14. Radioactive Man
The episode responsible for the terrible band “Fallout Boy”, Radioactive Man is peak Simpsons where pretty much every other line is quotable and hilarious. It’s a knock on the Hollywood machine and what happens when small towns come in contact with that machine; essentially ripping on the phony Hollywood types and the people and industries that attempt to rob them blind. This is one of a handful of Milhouse episodes, in which he is cast as Radioactive Man’s sidekick, Fallout Boy. This episode has aged extremely well with all of the superhero movies that have come out in recent years and is responsible for one of the greatest quotes in television history. “My Eyes… The goggles do nothing!”, outside of that it explores some of the seedier sides of Springfield (the abandoned Spirograph factory, for example) and shows the dark side of child acting (Mickey Rooney might show up to your treehouse – scary!).
13. Bart Sells his Soul
The Simpsons don’t shy away from important topics like religion or politics and typically when they do (or rather, did) focus on those topics you knew that they were going to have something important to say (as opposed to shows like Family Guy that typically just make the easy jokes without raising any important questions). In this episode, Bart sells his soul to Milhouse for $5 and immediately regrets it. It’s a really deep episode that shows why there are classes at colleges that study The Simpsons and it touches on what it means to be religious, to be spiritual and to be human. Like every episode in Season 7, there are countless quotables from this episode, but it’s the plot and philosophical side to this episode that showcase that not only was The Simpsons the funniest show on television at the time (and ever), it was also one of the deepest. This is The Simpsons at it’s very best.
12. King Size Homer
Homer has always been a heavy-set fellow but when he learns that he can essentially work from home if he reaches 300 pounds, he goes for it and ends up crushing his goal weight. With all the hilarity that you’d expect to ensue from Homer attempting to gain weight (“Towel rack!”) the episode ends up being unexpectedly poignant as his wife, Marge, struggles to deal with her husband’s new-found size. While he ends up realizing that it was a mistake and pledging to lose the weight, it’s his size that ends up saving the day and Springfield as a whole as his girth helps block the venting of radioactive gas. As Bart so brilliantly points out, it’s ironic that for once Homer’s butt was responsible for blocking the release of radioactive gas. One of the many meta-jokes that showed why the show was untouchable in it’s prime (Homer driving by in that stolen ice cream truck after Lisa defends him as not some sort of “food crazed maniac” is another example)and is funny on so many levels that it’s actually almost a crime that this episode isn’t rated higher.
11. 22 Short Films About Springfield
This episode, which was essentially a spoof on Pulp Fiction, showed why The Simpsons in it’s prime was better than any show on television and it’s because of its amazing supporting cast. The city of Springfield is the supporting cast of the show and while a lot of movies say things like “New York City was a main character!”, The Simpsons really means it when they say that an entire town is the supporting cast member of their show. There are countless supporting characters with rich backstories on the show and in the seventh season, it really begins to take advantage of the fact that there are a lot of characters that fans know and love. Essentially going around town from story to story and town member to town member, 22 Short Films About Springfield is The Simpsons at it’s most diverse as well as it’s best.
10. Bart of Darkness
Bart of Darkness is one of the most perfect examples of how the show’s early writers did a take on classic Hollywood cinema, in this case being the classic Alfred Hitchcock/Jimmy Stuart film Rear Window. After Bart breaks his leg attempting to jump from his Treehouse into the Simpsons’ new pool, he ends up spending the summer mostly alone in his bedroom as his sister deals with the popularity that comes from being the kid with a pool. This episode is great because it has a murder mystery at the core of it, even if the least guilty person in the whole town is the main suspect, i.e. Ned Flanders (which is what makes it all the more brilliant). Despite the fact that his sister has been shunning him all summer (and who can blame her? His play is TERRIBLE), he races to her side when he thinks that Flanders is closing in on her which shows at the end of the day that Bart is a good brother. Those tiny moments are what, again, distinguish this show from other shows about cartoon families (Sorry, Flintstones fans!).
9. Homer’s Barbershop Quartet
Homer’s Barbershop Quartet is essentially the story of the greatest rock band of all-time, Smash Mouth. I mean, The Beatles. It’s one of the first times that Homer has been in a band (We won’t talk about the “Sadgasm” episode) and it’s such a great episode because it masters one of the tropes that early Simpsons did so well (before things got all confusing and convoluted by contradictory backstories which will happen when you’re on the air for almost 30 years). After finding their fathers record for sale at a Flea Market, Homer sits his kids down to talk about the year in his life where he was essentially a part of the biggest band in Springfield. The bands rise and break-up ends up mirroring the Beatles story, beat for beat, leading up to an amazing finale where they all get back together on top of a building to perform their biggest hit “Baby Onboard”. If you’re a Beatles fan this episode is probably ranked a lot higher, especially when Moe has The Simpson‘s version of Yoko Ono’s drink on standby (A single plum floating in perfume, served in a man’s hat).
8. Deep Space Homer
While some may claim that this episode was the beginning of the goofy, out of this world adventures that the family got into (to the detriment of the show especially when compared the grounded realism of the initial episodes), it’s still a really, really funny episode (“HAIL ANTS”). Another amazing example of the show using celebrity cameos the right way, the sight of Homer and the flight crew silently floating in space while listening to James Taylor would make even Frank Grimes laugh. The Second Homer vs. Barney episode on this list; while the plot is literally out of this world, the show does a great job of explaining why it makes sense in The Simpsons world. Something that they haven’t done a great job of as of late. This was The Simpsons giving zero F’s and mocking shows on its own network (Married with Children) and others (Home Improvement), while also essentially showing that as long as the writing is crisp, witty and perfect they can send Homer anywhere and the show will be good.
7. Homer Goes to College
Another episode written by Conan O’Brien, Homer Goes to College is just… Perfect. After somehow causing a meltdown in a simulation with no nuclear material, Homer ends up having to cheat his way through his only class to maintain his job. A perfect example of The Simpsons writers understanding common tropes and turning them on their head (in this case with the “crusty old Dean” who also used to be the bass player for The Pretenders). This episode is like a mash-up of every bad college comedy from the past few decades… It’s not only good, but great. This episode is one of the first to also explore the idea of the ancillary damage that Homer and his family cause and what that means to other people. In this case being his roommates who end up getting expelled after running over the Dean in a “prank” (the funny thing is, some people on YouTube would call that a prank these days). While the next episode on this list does it better, this episode is just a gem and shows that Conan was peak… Conan back in the early 90’s.
6. Homer’s Enemy
Speaking of episodes that explore how Homer’s… Everything affects other people, Homer’s Enemy focuses on Frank Grimes a new hire at the nuclear plant who has had a pretty rough life. The point of this episode is to show how a real person would react to Homer’s dangerous stupidity and dumb luck. It’s done so well that you actually end up feeling bad for “Grimey” up until the point that he kills himself mocking Homer. It’s funny, The Simpsons gets such high marks for focusing on real-world issues and topics but at the same time it’s completely unrealistic and hilarious and it’s this episode that highlights the delicate balance between the two. While it’s a lot darker than episodes that preceded it, it’s still hilarious.
5. A Star is Burns
Perhaps the most polarizing entry on this list, A Star is Burns is one of the few examples of The Simpsons doing a cross-over show (or as Bart puts it, “A cheesy cartoon cross-over”). Co-Starring the main character of a long forgotten Fox cartoon in Jon Lovitz’s The Critic. That show was a cousin of sorts of The Simpsons as it was created by Al Jean and Mike Reiss, two former showrunners from The Simpsons. While the family from Family Guy stopped by and The Simpsons were a sort of running gag on Futurama, it was this episode that best took advantage of the cross-over by really treating it like any other episode. Sure, they referenced the fact that it was a cross-over but that wasn’t the main point of the plot. It came in the form of a film festival that Marge cooked up in the hopes of fighting off some bad press and getting more tourists to come to Springfield. Another gem that took advantage of the shows super deep cast of characters; there are numerous jokes that have zero to do with the Simpsons family and it’s because of that that this episode rates so high and the show is so great.
4. Mr. Plow
If you were to ask five of your friends to sing the Mr. Plow song I’d bet that more than half still know the words. That’s a testament to this episode that, while one of the oldest on this list, is still fresh in many people’s minds today. In this episode, Homer ends up getting talked into buying a pick-up truck at an auto-show and initially finds a lot of success in his plowing business (which he picks up to afford payments on the truck). It’s only after his best friend Barney Gumble steals his idea and buys a bigger truck (and does commercials with Linda Ronstadt) that the episode really takes off. There are almost too many great quotes to count here but the best parts of this show come from the Simpson families attempt to create their own television commercial, which runs once at three or four in the morning. Despite the fact that Homer ends up losing his truck to repo-men, he does get to keep his Mr. Plow jacket and that should make Marge happy for a long, long time.
3. Marge vs. the Monorail
Marge vs. the Monorail was written by none other than Conan O’Brien and it’s his work on The Simpsons combined with his Saturday Night Live, Late Night, Tonight Show and now work on Conan that goes to show that he’s one of the most brilliant comedic minds of all-time. While this episode is primarily a Homer episode, it also shows one of the ways that The Simpsons used to do celebrity cameos the right way (unlike that 50 Cent episode… Ugh). The late, great Leonard Nimoy is the celebrity that Springfield invites to its maiden monorail ride and the few minutes he spends on the show is filled with laughs (“Ahh, a solar eclipse, the cosmic ballet… Goes On…” “Does anyone want to switch seats?”) and the show isn’t cheapened because he’s there (which isn’t the case in more recent years). This episode was also probably the best use of Phil Hartman’s talents as well, as hard as that is to claim as his work as Troy McClure and Lionel Hutz are still missed to this day. It’s just a great episode and is probably Conan’s best work during his time on the show.
2. Krusty Gets Kancelled
Speaking of doing celebrity cameos the right way, Krusty Gets Kancelled was a play on the end of Johnny Carson’s run on The Tonight Show (and all the hubbub surrounding that). The show has countless celebrities on it as the Simpsons kids attempt to help Krusty get his show back on the air after a new children’s show titled “Gabbo” comes into town and steals all of his ratings. From Johnny Carson himself to Bette Middler (“We owned a race horse together… Kruddler”) or Elizabeth Taylor, the show is a who’s who of 20th Century Hollywood royalty. Yet, despite all of those famous faces, the show doesn’t allow them to take over or push their own agendas and it’s stuff like that, that should make the current showrunners ashamed of some of the move’s they have made in recent years (that Kesha “Tik Tok” cover immediately comes to mind). Krusty is always a win and while it came down to this episode or Homie the Clown in terms of the better Krusty episode, this episode wins because of it feels like a huge event even though you’re just watching a cartoon. That’s how invested you end up feeling with all of the characters on this show.
1. Lisa on Ice
For those of us that grew up playing hockey, The Simpsons gets no better than the hockey based episode, Lisa On Ice. While the Simpson’s children have pretty much played every sport, it’s the least popular of the four major sports that is the most brilliant as it essentially pits Lisa and Bart against one another in a battle for what amounts to their father’s love. Perhaps it’s most underrated and quote-filled episode, there are so many things that The Simpsons writers nailed here – most pop-culturally significant being the “air punching/kicking” fight between Bart and Lisa and Homer’s similar attempt with that pie. Ugh. So good. Beyond that, this is probably the best episode that explores the dynamic that exists between brothers and sisters and how parents can play favorites, especially when it comes to sports. It’s the small things like that that make The Simpsons the greatest sitcom of all time. While this isn’t even close to their most emotional episode ever, it is still leaps and bounds ahead of other “Best Show(s) Ever” like Seinfeld or Family Guy. And, because this episode so adeptly balances those elements it’s the best representation of The Simpsons at its peak.