Like a great many of my friends I speak a second language known as Simpsons quotes. We can recite the most arbitrary and unrelated lines yet still know exactly what we were talking about. You’d be amazed how many times I’ve actually said “Major Nougat, Gooey, Cocoa put down those entertaining Mattel products. It’s seems Colonel Captaffy is up to his old tricks”. No idea how that would ever be in context, but if you speak Simpsons that makes sense.
That said The Simpsons has entered it’s 40th season? I don’t know I stopped counting just like everyone in Chicago stopped counting how many years it’s been since the last Cubs World Series, point is it’s been awhile. So I will apologize in a sorry not sorry way that every one of the episodes featured on this list is from season 3-9. Let’s not kid ourselves, this is the golden age of what was the greatest show of all time, and I choose to largely ignore all the episodes that have followed. There are certainly some worthy moments in seasons 10-15, but the age of every episode being phenomenal clearly ended sometime in 1998.
I just watched these 7 seasons over again, and feel like they’re all fresh enough in my mind to arbitrarily rank them. I apologize in advance for missing your favorite episode on this list, trust me there were some great episodes that got the axe like Groundkeeper Willie in Treehouse of Horror V, but what’s left is pure gold like Chester J. Lampwicke’s solid gold rocket car. Forgive me if my commentary for each episode is little more than a sampling of some of my favorite lines.
30. Homie the Clown - Season 6
There are two reasons why this episode is appearing on this list. For starters there’s the scene early on when Homer pictures his entire family as smiling dancing clowns and interjects “This family has stood in my way long enough, I’m going to Clown College”. The other involves Homer’s many failed attempts at performing the tiny bicycle trick. Along the way are countless Krusty throwing his money away jokes, speed holes, Batman references, and all the other things that made every moment of season 6 amazing.
29. Homer’s Enemy - Season 8
This is perhaps better known as the Frank Grimes episode. The Simpsons found a way to make tragedy hilarious. Frank Grimes is the man who had to struggle for everything, who naturally finds a way to resent everything about Homer’s dumb luck. Homer is at his most irritating and hilarious simultaneously in this episode, stealing Grimes pens, causing several near meltdowns, and winning a children’s model building contest. Grimes on the other hand just can’t catch a break, and his suffering is pure comic gold. This also features Bart owning his own factory which offers it’s own great subplot.
28. The City of New York vs. Homer Simpson - Season 9
This episode has garnered a bit of notoriety in last 14 years as an homage to the Twin Towers. Barney is the designated driver and proceeds to go on a month long bender leaving Homer’s car parked between the World Trade Center buildings. Homer has his own disastrous feelings towards New York City that only get reinforced, while the rest of the family makes the most of their day. This also is responsible for me referring to Mountain Dew as “Crab Juice” for the past 17 years, and laughing every time I hear Flushing Meadows.
27. The Springfield Files - Season 8
One of the few memorable crossovers the Simpsons did, this time featuring agents Mulder and Scully of the FBI. Homer gets drunk, sees an alien, and hilarity ensues. This episode starts with a bang with the TGIF opening montage, including Homer describing the plot to Speed and calling it “The Bus That Couldn’t Slow Down”, and features such quotable lines as “Whoever thought a whale could be so heavy?”, “His jiggling is so hypnotic”, and the late Leonard Nimoy’s “Surprise me”.
26. This Little Wiggy - Season 9
Ralph episodes were few and far between in the early days. There were some great moments for sure, but season 9 featured just the second episode starring Ralph Wiggum, the first being I Love Lisa from season 4. After the initial Knowledgeum segment, Ralph introduces Wiggle Puppy, which I thought was the funniest god damn thing I ever saw at the time. Bart reluctantly hangs out and makes good use of Chief Wiggum’s master key, until Mayor Quimby almost gets electrocuted and a leprechaun tells Ralph to “Burn the house down. Burn ‘em all!” I also can’t even estimate how many times I’ve yelled “Woo-hoo, beer beer beer, bed bed bed!”
25. $pringfield (Or How I Learned to Stop Worrying and Love Legalized Gambling) - Season 5
The title might be another of the million or so Stanley Kubrick references the show has made over the years but this one is all about gambling. It features Homer’s faultless memory recalling the town hall meeting, and one of the few times Marge is the one with a problem. The highlight to me is still Homer’s panic about the boogie man or possible “Boogie men”. This also has the great breakfast recipe of frozen pie crust, vodka, and cloves. It’s worth it alone for Lisa’s costume and Ralph delivering the immortal line “I’m Idaho”.
24. I Love Lisa - Season 4
As far as I can tell this is the first time we got a proper introduction to Ralph Wiggum. Until this episode he was more of a background character who had a completely different voice in Lisa’s Pony. There were probably a dozen awkward dates in my life when I wanted to say “So, do you like stuff?” thanks to this episode. This has the great clip of Sideshow Mel whacked out on wowie sauce, and plenty of Chief Wiggum sex appeal. My friends quoted this episode so much we even got a non-Simpsons watcher to start regularly saying “Away with thee, lest my cane find your backside”. This episode’s homage to the mediocre presidents is still one of the best musical moments in the shows history.
23. Bart Sells His Soul - Season 7
“I need a soul Ralph. Any soul. Your soul (flashlight) hissssssssss”. That segment right there is 100% of the reason this episode made my list. That doesn’t mean “Remember Alf? He’s back, in pog form” isn’t it’s own gem, but Bart hissing is damn near the best thing ever. The subplot of this episode involves Uncle Moe’s Family Feedbag which is it’s own source of awesomeness. “Oww my freakin’ ears”, “40 seconds, but I’m hungry now”, “Way to breathe no breath”, and “Help he’s spraying funny smelling water on me” are all highlights.
22. Burns, Baby Burns - Season 8
How do you make the greatest show on TV better? Put Rodney Dangerfield in it. Rodney plays Larry Burns, and proceeds to be Rodney Dangerfield all over this episode. Like his legendary appearance in Caddyshack, literally every single line he has in this episode is brilliant. Working at a bar that sold cider I must have said “If it’s clear and yella you got juice there fella. If it’s tangy and brown, you’re in cider town” a few hundred times thanks to this episode. This has so many great Dangerfield lines that it takes several viewings to get them all down, but I gotta say “I hope I look that good when I’m 200” has got to be the winner.
21. Last Exit to Springfield - Season 4
As a kid when I first saw this episode this was the “Dental plan! Lisa needs braces” episode. In the years since no other episode has been cited as the best ever by numerous sources. I’ll admit the episode is nearly flawless, but so are the other 20 episodes ahead of it. Grandpa telling a story about tying an onion to his belt, “Which was the style at the time”, and Burns reading “It was the best of times, it was the blurst of times? You stupid monkey”. I’d be lying if I said I didn’t wake up this morning thinking “That’s a nice a donut”, despite not having any donuts in house. This is definitely one of the most packed episodes and there seems to be a pop culture reference every 30 seconds including Batman and How the Grinch Stole Christmas.
20. Homer the Heretic - Season 4
This episode is one of those somewhat forgotten gems that you realize later is just pure gold. The Simpsons might have been considered controversial in their day, but the idea of Homer simply abandoning church for all the right reasons always made this episode stand out for me. For someone growing up in Chicago I can certainly sympathize with Homer’s desire to stay in a warm comfy bed during a brutal winter morning. The fact that he has the greatest day in his life all thanks to skipping church always gave me a chuckle. Perhaps Homer dancing around a crashed beer truck stands out as perhaps the best visual gag. One of my many, many favorite Homer lines is still “Everyone is stupid except me.”
19. Selma’s Choice - Season 4
Another season 4 episode this is perhaps better remembered as the Duff Gardens episode. Like many other great episodes there are too many awesome moments to mention. Lisa delivers perhaps her best line of the series with “I am the Lizard Queen”. Few things have been as consistently hilarious as Homer’s giant sub that he keeps eating no matter how disgusting it gets, “Duff Gardens hurrah!”. Let us not forget another randomly quotable line like “Homercles cares not for beans.” As a kid this is probably the first time I encountered the phrase drunk glasses, which are employed to hilarious effect. Thanks in part to Minnesota’s best brewery the line “Hey Surly only looks out for one guy, Surly” has taken on a second life.
18. Homer’s Phobia - Season 8
This is another gem from the 8th season that features a memorable guest voice actor, one more still to come. John Waters plays the owner of a store of random knick-knacks and vintage memorabilia that I always wanted to visit as a kid. Along the way we find out Homer is a bit of a homophobe and in a time when that was still the subject of great comedy, Homer’s intolerance leads to greatness. The gay steel mill is still one of the best things in any show ever and all the increasing Bart might be gay moments only help fuel Homer’s recklessness and the humor. We also get a rare glimpse that Mr. Smithers might not just be into Mr. Burns. Like most times Homer is horribly wrong he does eventually come around making this rather progressive for the time.
17. The Joy of Sect - Season 9
This came as a bit of a delayed reaction the Heaven’s Gate nut jobs and that random mid-90s fascination with cults. I remember running through the halls of my high school yelling “Out of my way, jerk ass” after this episode premiered and that never got old. Like Last Exit to Springfield a good chunk of humor is had early on by making Homer out to be some incorruptible genius. Marge is the voice of reason, and like many times before it, beer saves the day. Marge’s escape from the Movementarian compound is great including a Prisoner reference that was lost on 14 year old me. One of the gags often cut from syndication showed Lenny worshiping a box of Special K that he holds up after Mr. Burns’ failed attempt at starting his own religion.
16. Last Temptation of Homer - Season 5
There was a time when damn near every second of every Simpsons episode was awesome, and this is one of those. Before Mindy is hired, Burns horrible hiring practices are shown including Stuart the duck and damn near my favorite anything foreigner Zutroy. The main story has it’s share of laughs including Homer and Mindy’s horribly awkward elevator ride together. The secondary story however features Bart the nerd which might even be better. It’s hard to think of another episode with more references, everything from Barney singing the theme of “I Dream of Jeannie”, Mr. Burns’ disastrous flying monkeys, Hogan’s Heroes, Jerry Lewis, The Birth of Venus, and a Buddhist chant that I only recently caught on to.
15. You Only Move Twice - Season 8
Albert Brooks, brother of show’s producer James L. Brooks appeared on a number of Simpsons episodes, always as a different character. As much as I like Brad Goodman, his turn as Hank Scorpio is easily his best. The episode makes the quite hilarious suggestion that maybe a Bond villain could be a really awesome guy. Few episodes show Homer excelling so readily and their new life turns out nearly perfect. Marge starts drinking, Lisa is allergic to everything, and Bart is put in special ed classes. Watching the commentary I found that the whole hammock scene was completely improvised by Brooks and Dan Castellaneta which is just pure genius. I always had a laugh at Homer ending the episode as the owner of the Denver Broncos, who one year later would wind up winning their first of back to back Super Bowls.
14. Duffless - Season 4
Before this episode, and truth be told after it, alcohol and beer were usually just comedic jumping off points. For the first time the negative effects of Homer’s drinking are brought up, but still hilarious. I couldn’t help but appreciate the Queen reference in Homer’s rendition of “It Was a Very Good Beer”. Like nearly every episode from this season there is a Stanley Kubrick reference, when Bart reaches for two cupcakes and collapses in the fetal position like Alex in A Clockwork Orange. This has one of my many favorite Milhouse moments when he says “Behold gravity in all it’s glory” during the science fair. I will say no matter how much I’ve wanted a beer I can’t say I’ve ever pulled a Homer and ate the dirt under the bleachers.
13. Hurricane Neddy - Season 8
This was an odd episode for me in one regard, I missed it’s initial premiere. I didn’t see it until about two years later in syndication, and was probably several more years when I saw it completely intact. It didn’t take long though for this to become one of my absolute favorites and it was the first episode that let me know how irritating it can be to watch a Simpsons episode with people who have seen it way too much. A friend of mine in the Marines and I decided to recite every single line of this episode for our fellow Marines and despite how hilarious it was to us, they weren’t as amused. Flanders losing his shit is just priceless, calling out the entire town and finally snapping after years of near perfect behavior was one of the shows most satisfying moments. Naturally any reference to Ned’s beatnik parents is also worth the price of admission. To date I still can’t look at a rubix cube and think “spin it topwise, topwise”.
12. Cape Feare - Season 5
You can feel free to scroll ahead, seriously don’t though that’s a dick move, but this is my favorite Sideshow Bob episode. For years it was Sideshow Bob’s Last Gleaming, but this hilarious parody of Cape Fear is just brilliant. This has Homer’s infamous “Bart you wanna see my new chainsaw and hockey mask” moment, and of course Terror Lake saluting Hannibal Crossing the Alps with elephants. Two particular gags never, ever get old here; the first is Homer trying to learn his new identity with the incredibly frustrated witness relocation agents, the other is of course Sideshow Bob stepping on 13 rakes. It’s a wonder of comedic timing that takes a funny gag and stretches it to absurdity and back to hilarity. Family Guy has made an entire show of stretching jokes out too far, but nothing quite matches this.
11. And Maggie Makes 3 - Season 6
In the Simpsons golden age every season had a few themed episodes. There was usually a Lisa episode, a Marge episode, a vacation episode, Sideshow Bob, and a flashback episode. As much as I love Lisa’s Sax (which just missed the cut for this list), And Maggie Makes 3 is the best of the bunch. The flashback starts with Homer saving the plant from terrorists, Die Hard style. Once forced to tell the story right, he winds up quitting the Nuclear Power Plant in the most satisfying way possible, including playing Mr. Burns’ head like a bongo and literally burning his bridge while leaving. Aaron L Aronson and Mr. Zublikowski is one of my favorite Patti and Selma moments, and you can’t beat how slow Homer is picking up the hints that Marge is pregnant again.
10. 22 Short Films About Springfield - Season 7
The genesis for this episode was the end of the Season 4 episode The Front, which had an ending segment “The Adventures of Ned Flanders”. So with a loosely tied together narrative Milhouse and Bart wonder if anything interesting happens to the other residents in town. By my count there are more like 19 short films about Springfield, but that’s far from the point. Naturally with the structure of the show every segment is too fast to really catch everything on first, second, or 40th viewing. This introduced such memorable lines as “Donuts, I got donuts”, “Mmm, steamed hams”, and “You took four minutes of my life and I want them back, eh I’d just waste them anyways”. This is a masterpiece of multiple stories, writers, and characters brilliantly woven together. Like most of the best episodes, I could go for another 2 hours of this.
9. Homer vs. the 18th Amendment - Season 8
It wasn’t until I recently finished revisiting Season 8 that I decided this was my favorite episode of the season. The Simpsons have had numerous laughs at the expense of drunkenness, and I would say the beginning of this episode perfectly sums up why I hate St. Patrick’s Day. Marge also makes a good point that Homer’s bootlegging operation is by far the most clever thing he ever did. Dave Thomas plays Rex Banner and he embodies every stereotype of G-Men from 30s movies to a T. The first time I saw him ask Barney “Where’d you pinch the hooch? Is some blind tiger jerking suds on the side?” I was in tears. This also features possibly the truest line in Simpsons history, “To alcohol, the cause of and solution to, all of life’s problems.”
8. Homer Bad Man - Season 6
“Just thinking about her sweeeeet can.” “I think we need less Homer Simpson, and more funding for public schools.” “Homer sleeps nude in an oxygen tent, which he believes gives him sexual powers.” Candy shaped rat poison convention. Homer shaking up pop rocks and buzz cola. “Oh yeah, oh baby.” “Ben, no!!!!” “Can you introduce me to the Sasquatch, I like his style?” “Ooh portrait, sounds classy.” “That’s your solution to everything, live under the sea.” I think I’ve made my case.
7. Homer at the Bat - Season 3
The earliest episode on my list, this is in my opinion the first phenomenal episode of the show. In a wonderful parody of The Natural, Homer makes his own bat and proceeds to be a star on the plant’s softball team. Mr. Burns decides to make things interesting by hiring ringers, as always some laughs are had at the expense of Mr. Burns dated references including Honus Wagner, Cap Anson, and Mordecai “3 Finger” Brown. I’ve probably quoted every line of this episode over the years watching baseball, particularly “Hey you, hit a home run.” Damn near the best sound effect the show had is when Mr. Burns has Smithers massage his brain. When Roger Clemens and Ken Griffey Jr. who respectively suffer from hypnotism gone awry and gigantism finally retired it was the end of an era in baseball. To date I can’t watch a Dodgers game without thinking “I thought I told you to trim those sideburns Mattingly, that’s it you’re off the team.” Jose Canseco might be best known as the living embodiment of steroids in baseball, but I’ll always first think of him as the player who helped save a burning woman’s house, including her player piano.
6. Lemon of Troy - Season 6
The second but not last season 6 episode in my top ten. Lemon of Troy is one of those classic episodes where nearly every time you watch it you discover a new favorite moment. Like Homer Bad Man I could probably just rattle off every favorite line and I think I will. “Hey, there’s a lemon behind that rock.” “I thought you said you could read lips.” “I assumed I could.” “But Milhouse is my name”. “Your wussiness better come in handy.” “Run faster boy, he’s got the taste for meat.” “That’s a crud rock, it belongs in crud town.” “You’re stupid, you stupid weak baby.” This is about as idyllic as The Simpsons ever got towards Springfield and it’s hard not to love the origin of Springfield and Shelbyville.
5. Lisa the Vegetarian - Season 7
Paul McCartney was the last of the Beatles to make a guest appearance on The Simpsons, but he picked the best episode, as much as I do love Homer’s Barbershop Quartet. Before I get to Lisa I’d like to point out that this has my favorite Ralph Wiggum line ever “Oh boy, sleep! That’s where I’m a Viking.” I’ve had more than one birthday celebration invite named “Homer’s big backyard BBBQ, the extra “B” is for BYOBB”. I’m sure every person who has seen this episode has at one point in their life sang “You don’t win friends with salad.” This episode is remarkable in sitcom history for actually instituting a permanent character change, where Lisa has remained a vegetarian since. Apparently this was one of the requirements for Paul McCartney to appear in the episode. There are some great set up jokes here, like Mr. Burns charity joke about when pigs fly, and Apu singing “Sgt. Pepper’s Lonely Hearts Club Band.” Another classic example of a great show getting countless laughs out of a somewhat important issue.
4. Lisa on Ice - Season 6
I could easily flip-flop these two episodes as my favorite Lisa episode, but once upon a time Lisa on Ice was my absolute favorite. “Look that kids got bosoms.” “Hack the bone!” “We paid for blood.” “Me fail English, that’s unpossible.” Homer randomly biting air before hitting his head on the stove and taking Marge’s pie never gets old. Lisa’s cutaway to Monster Island is also great, especially the line about it being a peninsula. I also love Marge’s attempt to bond with Bart offering play “the basketball. I’m no Harvey Globetrotter”. Lisa deflating her volleyball teams only ball is a perfect bit of animation. This does get the slight edge over Homer at the Bat as the shows best sports related episode.
3. Itchy and Scratchy Land - Season 6
The best of the many vacation episodes the Simpsons have had. Perhaps the greatest bit of animation in the shows history comes from the reaction shot of Bart and Lisa as Marge explains their upcoming trip to the Bird Sanctuary as opposed to Itchy and Scratchy Land. “Everything’s too damn expensive, like this bible. $15, and talk about a preachy book, everyone’s a sinner. Ooh except for this guy.” I’m not sure I’ve pronounced the word “possibly” correctly since this episode premiered. I’ve never been a fan of personalized items, but this episode got a good deal of mileage out of Bort license plates. In my younger beard-less days my looks were compared to John Travolta often, and I would naturally reply “Yeah, looks like.” This is the episode that just keeps on giving. “My children need wine.”
2. Rosebud - Season 5
My favorite all time episode hasn’t changed over the past 15 years or so, but I had no idea what would take the second spot. This episode may begin with a Citizen Kane reference and end with Planet of the Apes, but the Simpsons were never funny solely because of their references. Homer sitting down and eating 64 slices of American cheese in the middle of the night is pure disgusting comic gold. The Ramones make a brief appearance at Mr. Burns’ birthday party. Homer’s impersonation of Mr. Burns at his birthday is that perfect mix of low brow humor that makes the show so damn brilliant. It may be the fact that Citizen Kane is my favorite movie and there is just enough parody here to satisfy my film nerd heart.
1. A Star is Burns - Season 6
Anyone who has hung out with me during a long Simpson’s quote-a-thon won’t be surprised that this is occupying the number one spot on my list. I was a huge fan of the show The Critic, and despite the fact that it was cancelled criminally early, Jay Sherman got a bit of a second life with this episode (and a very brief cameo in Hurricane Neddy). Probably the two best sound effects in the history of the show are in this episode. The first being clearly Hans Moleman getting hit in the groin by a football, and the other Jay Sherman’s legendary belch. This has Mr. Burns saying “An ogre, I outta club them and eat their bones”, Barney’s greatest line “Just hook it to my veins”, and of course “You suck, McBain”. In the dozens of times I’ve seen this episode since declaring it number one it’s just reinforced itself as the right choice. So argue away, and feel free to let me know if there’s any reason to watch an episode from the last decade or so.
