Top Ten Simpsons Episodes of All Time

Our look at The Simpsons ends with my ten favorite episodes. In a way it slightly saddens me that all 10 episodes come from seasons 3-8. I wasn’t surprised that none of the episodes from the first two seasons made it – they were still finding their stride in the early years. But I cannot believe that it has been 13 years since the last of my absolute favorites came out. Of course, when you have a show that 445 episodes and counting, it’s tough to come up with 10, but I did and here they are.

10. Homer at the Bat (Season 3)
What is there not to love about this episode? From Homer’s flashback to the night of the thunderstorm when he made Wonderbat (“Grabbing a large piece of sheet metal, I took cover under the largest tree I could find”), to eight of the nine ringers meeting some sort disaster which keeps them out of the big game (I love Ken Griffey Jr’s enlarged head, Roger Clemens squawking like a chicken, and Wade Boggs getting into a fight over who England’s greatest Prime Minister was with Barney best of all). Daryl Strawberry of course was the star of the show, getting to play a squeaky clean version of himself that everyone but Homer loves. The tear running down his check as Bart and Lisa taunt him is classic. Great references to classic movies The Natural and The Pride of the Yankees were also spot on. The Simpsons have done many episodes based around a sport (Bart in Pee-Wee football and Little League, Bart and Lisa going head to head in hockey), but this is the best of the bunch. Sing it with me know “We’re talking softball…”

9. Bart of Darkness (Season 6)
Season 6’s Season Premier was this twisted, hilarious send up of Alfred Hitchcock’s Rear Window. Bart and Lisa convinces Homer to get them a pool, and while Lisa becomes popular because of it, Bart breaks his leg and becomes increasingly withdrawn and scary, writing his own, and staring out the window with his telescope. He hears a woman scream next door and then sees Ned Flanders act suspiciously, eventually crying out “I’m a mur-diddily – urdler”. Sending Lisa to investigate, leads to consequences as Flanders comes home and starts stalking through the house with an axe, as Bart tries to get to her, and winds up dragging half the things he encounters on the way with him. The homage to Hitchcock is brilliant, using the same musical cues as the master’s film, and the episode even features a Jimmy Stewart caricature trapped in his wheelchair with a camera looking at Bart. While most of the best Simpsons episodes have a series of memorable quotes, this one doesn’t really have one that stands out (although I do love it when Homer sounds sarcastic at the end of the episode, or when he says “Doh-eth” when the Amish guy correctly tells him that they built a barn and not a pool. Instead, this episode is all about storytelling, and on that level, it has rarely been topped in The Simpsons cannon.

8. Duffless (Season 4)
If The Simpsons has always been a marriage between the more anarchic spirit of Matt Groening, and the sentimentality of James L. Brooks, then Duffless is one of the episodes that get the balance perfectly. Homer goes on a tour of the Duff Brewery with Barney, and then gets busted for drinking and driving. He agrees to go to AA meetings, and give up beer for a month for Marge. Meanwhile, Lisa uses Bart as her science experiment wondering if he is any smarter than a hamster. The episode is full of classic homages to films – Bart reaching for the cupcakes is a reference to A Clockwork Orange, Moe’s final dialogue where he points at the camera comes from Reefer Madness, the Raindrops Keep Falling on My Head sequence comes from Butch Cassidy and the Sundance Kid, and Bart stroking the hamster is a reference to the classic Bond villain Ernst Stavro Blofield. The film also has many classic moments, like Homer riding Lisa’s bike, and Ned Flanders confession that he was more animal than man when he drank that raspberry schnapps and called Ann Landers a “boring old biddy”, Chief Wiggum rolling down the hill in a giant beer stein, and later mixing up DOA and DWI. The ending of the episode, where Homer chooses Marge over beer, and the two go on a bike ride together is one of the most beautiful moments in the shows history. In lesser hands, it would have been overly sentimental, but here it is just about perfect.

7. Rosebud (Season 5)
In this classic homage to “the greatest movie ever made”, Citizen Kane, all Mr. Burns wants is his cherished childhood bear Bobo, that has found its way into Maggie’s possession. The film brilliantly plays off the legendary movie, with Burns and Smithers walking around in Burns’ own personal Xanadu, with his cherished possessions, including “King Arthur’s Excalibur, a nude photo of Mark Twain and that rare first draft of the constitution with the word suckers in it”. The episode also features a memorable cameo by The Ramones, who rattle Burns so much that he order Smithers to have the Rolling Stones killed. My favorite quote is Apu’s when Bart tells him that there is a head in the bag of ice and he replies “Oh, a head bag. Those are chock full of… heady goodness”, although Homer saying he’ll never wag his ass in public again, and Lisa’s response “I’d like to believe that this time, I really would”, is a close second. Rosebud does what The Simpsons does best – mixing intelligent references with stupidity and coming up with comic gold.

6. I Love Lisa (Season 4)
I cannot help but love Ralph Wiggum. He is so gloriously clueless, that almost every word out of his mouth is comedy gold. This is far and away the best “Ralph” episode. Lisa, feeling sorry for Ralph on Valentine’s Day gives him a Valentine when no one else did, making Ralph fall in love with her. She then breaks his heart on national TV (Bart relishes watching it in slow motion where “you can pinpoint the exact moment when his heart rips in half”). Then Ralph and Lisa have to do a school play where they play George and Martha Washington. So many great lines in this episode – Ralph’s “The doctor said I would have less nose bleeds if I just kept my finger out of there”, Miss Hoover’s line to Bart “Do you want to act like a madman, or do you want to play John Wilkes Booth”. There are other classic moments – Skinner’s Apocalypse Now inspired Vietnam flashback, Chief Wiggum chasing a duck to try and get his badge back, Skinner making Willie water down the orange and of course the DJs on the radio constantly playing Monster Mash by mistake on every holiday. I Love Lisa is a perfect Simpsons episode, as it combines everything that is great about the show in one episode.

5. Sweet Seymour Skinner’s Baadassss Song (Season 5)
I choose this episode for a spot on my top 10 list for one simple reason – it has my favorite Simpsons quote in history. Bart gets Skinner fired accidentally, and Flanders is hired to replace him. The place quickly turns chaotic as Flanders refuses to discipline the students, but Superintendant Chalmers doesn’t really care – that is until Flanders goes on the PA system to thank the lord for a another beautiful school day. That is when Chalmers utters the line “That sounded like a prayer. A prayer in a public school. God has no place within these walls, just like facts have no place within organized religion”. Best. Line. Ever. The rest of the episode is also great with Groundskeeper Willie ripping off his shirt and telling the lunch lady to “Grease me up, woman” so he can squeeze into the air ducts, and Skinner’s response to Bart’s suggestion of making a pass at his commanding officer to get out of the army. “Done and done. And I mean done”. The brilliant Aliens homage in the air ducts, Skinner’s confession that he was shot in the back in Vietnam at a USO show trying “to get Joey Heatherton to put some pants on”, and his idea for a novel that sounds suspiciously like Jurassic Park called “Billy and the Cloneosauras” that Apu rants on and on about. In short, the producers made the right decision to make this the 100th episode, even if my favorite character Homer is barely in it.

4. Homer’s Phobia (Season 8)
In this episode, a trip to the mall leads to The Simpsons meeting John (John Waters), who loves campy things who Homer takes an immediate liking to. That is until he finds out that John is gay, and then worries that hanging around him will turn Bart gay as well. Homer hilarious takes Bart around trying to do manly things – making him stare at a billboard of two scantily clad women having a pillow fight and smoking, and then taking him to a steel plant, only to find out that the entire steel industry has gone gay (“There’s a spark in your hair”, “Get it out, get it out!”) The episode culminates with a hunting trip, that goes awry, and Homer, Moe and Barney taking Bart to Santa’s village to kill a reindeer, only to be saved by John. The best line in the episode is Moe’s (“Saved by a sissy. Looks like it’s suicide again for me”). Along with being one of the funniest episodes the series ever made, this was also quite a daring look at homophobia, a subject that remains taboo all these years later. This one is pure genius.

3. Last Exit to Springfield (Season 4)
“Lisa needs braces.” “Dental Plan.” “Lisa needs braces.” “Dental Plan.” “Lisa needs braces.” “Dental Plan.” “Lisa needs braces.” “Dental Plan.” “Lisa needs braces.” “Dental Plan.” “Lisa needs braces.” “Dental Plan.” “If we give up our dental plan, I’ll have to pay for Lisa’s braces!” That is one of classic bits in Simpsons history, as it shows just how slow Homer’s thought processes really are. But this episode is far more than just one brilliant joke. Last Exit to Springfield combines The Simpsons gift for lowbrow humor, with its incredible intelligence. The episode is a brilliant send up of labor unions, and has too many classic scenes and lines to mention them all. I love Lisa’s visit to her horrible dentist (who was supposed to be played by Anthony Perkins, before he got sick and died), the negotiations between Burns and Homer, where first Homer thinks Burns is coming on to him, and then later contains the most intelligent urine joke ever written. Grampa’s story about onions that goes nowhere is another highlight, as is the flashback where a young guy tells Burn’s grandfather that if they’re not careful the Japanese will overtake them to which he replies “The Japanese? Those sandal wearing goldfish tenders? Haha! Bosh! Filmshaw” (I like it, because I’m pretty sure that’s the only time I have ever heard the word Filmshaw). This episode is absolute genius.

2. Homer’s Enemy (Season 8)
One of the worst kept secrets in Springfield is that Homer is incompetent and lazy, but no one ever seems to mind or notice. That is until Frank “Grimey” Grimes gets hired at the power plant, and is amazed at just how stupid Homer really is. Grimey becomes more and more infuriated at Homer’s incompetence, even as Homer tries to win him over. But a trip to the family house only makes Grimey angrier, as Homer lives in a nice house, while Grimes lives in an apartment above a “bowling alley and below another bowling alley”. Finally snapping, after Homer enters a contest for children and wins (“Homer beat their brains out”), Grimey goes on a rampage through the power plant, eventually killing himself. Everything about this episode is absolute perfection. Hank Azaria’s brilliant work as Grimes, Homer eating like a duck and even the subplot about Bart owning a factory downtown that eventually collapses (“I was watching. First it start to fall over. Then it fell over” Milhous tells him). I particularly loved the scene when Grimes comes over to the Simpson house and is amazed by all the stuff Homer has done. Also love that Homer doesn’t know what a 513 is and keeps checking his watch, or Homer admitting he didn’t even know what a “nuclear paner plant was”. Homer is the most lovable oaf in television history, but I loved this episode where someone finally called him out on being an idiot.

1. Cape Feare (Season 5)
At its best, The Simpsons is the best show in television history for poking fun at pop culture. Nowhere did they do this better then in this brilliant send-up of the Martin Scorsese remake of the classic thriller, Cape Fear, which is much better than either movie version. In his third appearance on the show, Kelsey Grammer as Sideshow Bob starts sending Bart threatening letters written in blood from jail. When he gets out, he starts stalking the Simpsons – going to movies with him and laughing hysterically at the latest Ernest movie, or lying in the middle of the street, just before a parade comes by. The episode ends as Bob tracks the Simpsons down on their new houseboat and tries to kill Bart. There is hardly a scene in the episode, or a line that isn’t a classic. Homer not understanding the FBI agents when they tell him he’ll have a new name in witness protection, Sideshow Bob wanting Marge to repeat her last line because he came up with a better response, the drive through the cactus patch, The Simpsons singing the Mikado, Bob singing HMS Pinafore, and then being captured by the police because they drifted by a brothel. Chief Wiggum telling Lou and Eddie to “Bake away toys”, or the parole board asking Bob to change his wording from “urine soaked hellhole” to “pee-pee soaked heckhole” before concluding that “No one who speaks German can be evil”. All of this would be enough to put this episode high on the list of the best in history. But we all know what puts the episode over the top, and vaults it into my number 1 spot. The rakes. Never have a seen a more gloriously stupid, or hilarious gag, then Sideshow Bob getting out from under The Simpsons car and stepping on rake after rake then grimacing. Pure, unadulterated genius.