Pardon My Zinger - The 10 Greatest Simpsons Episodes Ever

With Amerca's longest running show reaching its 20th anniversary our specialist in all things simpsons, Matthew Kleebauer has compiled his top ten list

1. Last Exit To Springfield

Arguably the finest 22 minutes in the history of television, Last Exit To Springfield is the greatest example of why, for six golden and glorious years, The Simpsons was the funniest and the smartest thing going. Homer becomes leader of the Springfield Nuclear Power Plant Workers Union in a bid to win back their dental plan, and leads his co-workers to strike against the tyrannical Mr Burns. There are episodes with as many laughs in them as this, and there are certainly more moving ones, but what gives this the edge is the incredible volume of cultural references lovingly tucked away inside it: Moby Dick, The Godfather, Hubert Selby Junior novels, Jimmy Hoffa, Yellow Submarine, Batman, Dr Seuss, Charles Dickens, Citizen Kane…and these are just off the top of my head. It’s like an animated history of the 20th century. Anyone still clinging to the ridiculous notion that cartoons are merely for children should take a look at this and hang their head in shame. For many years I have maintained that watching The Simpsons makes you intelligent. Episodes like Last Exit To Springfield help prove my point.

Best bit:

Kent Brockman: Tonight, on Smartline: the power plant strike: argle-bargle, or fooferah? With us tonight are plant owner C. Montgomery Burns, union kingpin Homer Simpson, and talk show mainstay Dr. Joyce Brothers.

Dr. Joyce Brothers: I brought my own mike.

Brockman: Yes, well... Homer, organized labor has been called a lumbering dinosaur... 

[Homer screams.]

Brockman: OK, my director is telling me not to talk to you anymore... 

Homer: Woo-hoo! 

Brockman: Mr. Burns, you mentioned you wanted an opening tirade? 

Mr. Burns :Yes, thank you Kent. In 15 minutes I will unleash a terrible vengeance on this city. No one will be spared! NO ONE! 

Brockman: [chuckling] A chilling vision of things to come.

2. Deep Space Homer

Insert Brain Here. Those three simple words, tattooed onto his head by his mischievous son, are enough to convince Homer that maybe he needs to try and win the respect of his friends and co-workers. Coincidentally, appalling viewing figures for their most recent space launch has convinced NASA they need a new approach to their missions, and maybe sending an “average schmoe” into space will renew American interest in aeronautics. One prank phone call to President Clinton later, and Homer and Barney are suddenly part of a Right Stuff style-training programme to pick America’s newest hero. Deep Space Homer is, in my opinion, the funniest episode ever made, and plays like a highlights reel of classic Simpsons moments. From Homer’s inability to operate a touch-tone phone to Kent Brockman’s infamous on-air declaration (“And I, for one, welcome our new insect overlords”), from Barney relapsing into a drunken stupor from drinking non-alcoholic champagne to the ticker-tape parade for an inanimate carbon rod, from Buzz Aldrin’s meeting with Homer (“Excuse me Buzz, if in fact that is your real name”) to the zero-gravity potato chips sequence, it is hardly a surprise that a copy of this episode was requested by NASA and permanently remains at the International Space Station to be viewed at their leisure. If I were an astronaut I’d be proud of it as well.

Best Bit:

Mr. Burns: Compadres, it is imperative that we crush the freedom fighters before the start of the rainy season. And remember, a shiny new donkey for whoever brings me the head of Colonel Montoya.

3. And Maggie Makes Three

In first place we had the smartest episode ever. Second belonged to the funniest, but the bronze medal goes to far and away the sweetest Simpsons ever made. This is the third and final show detailing the births of Homer and Marge’s three children. During a period of (Marge-initiated) “family time”, they flick through the photo album, only for Bart and Lisa to wonder as to why there are no photos of Maggie. Homer then regales us with the touching story of her birth, and the episode takes the form of a flashback to 1993. Homer, miserable in his job at the Power Plant, is on the cusp of financial solvency for the first time in his life, and thanks to careful budgeting and planning, is able to quit and pursue his dream career: working at Barney’s Bowl-A-Rama. After going out celebrating with Marge, they return home and one thing leads to another, resulting in Marge becoming pregnant again. Marge tries to keep this a secret for as long as possible, but eventually he finds out, and the added monetary strain on the household forces him to return to the Plant, distraught and completely unenthusiastic about the impending birth. Of course, all it takes is one look at Maggie for him to fall instantly in love with her, but the true beauty of this episode lies in its final shot. Bart and Lisa still don’t understand how this story explains the lack of any Maggie baby pictures, but Homer clarifies that the pictures do exist, its just that he keeps them where he needs them the most. You see, on returning to the plant Burns issued him with a “special demotivational plaque to break what's left of your spirit”, which sits directly in front of his seat at work, and reads “DON’T FORGET, YOU’RE HERE FOREVER”. The episode ends with us looking at Homer’s workstation, and the plaque has been covered in pictures of his youngest daughter. Through careful placing of the photographs, the inscription now reads “DO IT FOR HER.” Gulp. I’m welling up just thinking about it.

Best Bit:

Announcer: We now return to "Knightboat: the Crime-Solving Boat".

Michael: Faster, Knightboat! We’ve gotta catch those starfish poachers.

Knightboat: You don't have to yell, Michael, I'm all around you.

Michael: Oh, no! They're headed for land. We'll never catch them now.

Knightboat: Incorrect: look! A canal.

Homer: Go, Knightboat, go!

Bart: Oh, every week there's a canal.

Lisa: Or an inlet.

Bart: Or a fjord.

Homer: Quiet! I will not hear another word against the boat.

4. Marge Be Not Proud

The Simpsons have always produced the best Christmas specials, ever since the very first full-length episode way back in 1989, Simpsons Roasting On An Open Fire. Somehow the two have become intrinsically linked in my mind; Christmas just wouldn’t be Christmas if I didn’t have a drink and watch at least a few classic episodes with my brother. Marge Be Not Proud definitely helps to explain this phenomenon. Obsessed with the newest beat-em-up videogame Bonestorm, Bart is dismayed when Marge tells him she thinks it glorifies violence and refuses to buy him a copy. At his lowest ebb, Bart visits the local Try-N-Save supermarket and shoplifts a copy, only to be caught in the process. The security guard takes pity on him though, and doesn’t press charges, on the grounds that he never returns to the store. Sadly, said Try-N-Save is where Marge intends to have the family Christmas portrait taken, and when Detective Broka spots the family, the inevitable happens. Marge’s steadfast refusal to believe her only son could be guilty of such a thing, only to be confronted with the security footage that proves otherwise is a genuinely heartbreaking moment, as is Bart’s angst when his loving and protective mother suddenly becomes cold and distant to him afterwards. Like all good Simpsons though, things end well and Christmas is saved, but for the audience to go through such a maelstrom of emotions, and in such a short space of time at that, is further proof that in spite of their skin colour the Simpsons truly are the most realistic and genuine family to ever appear on television.

Best bit:

Homer: Stealing! How could you?! Didn't you ever listen to that guy who gives those sermons at church, Captain What's-his-name?! We live in a society of laws. Why do you think I took you to all those "Police Academy" movies, for fun!?! Well I didn't hear anybody laughing, Did you!?! Except at that guy that made sound effects! [Homer proceeds to imitate Michael Winslow. He laughs, then...] Where was I? Oh, yeah, stay outta my booze!

5. Cape Feare

The freedom allowed to the creators of the show by choosing an animated series over live-action means that nearly every whimsical idea they have can be indulged in one way or another. This has resulted in some of the greatest movie tributes of all time, my favourite of which has to be Cape Feare, a episode –length tribute to the 1962 Robert Mitchum and Gregory Peck movie Cape Fear, as well as the 1991 Martin Scorsese remake (plus a host of other classics, including Psycho and The Night Of The Hunter). Bart’s nemesis, the deranged Sideshow Bob, is somehow released from prison, and mirroring the plot of said films, embarks on a campaign of terror against the family that wronged him, which results in them having to up and leave Springfield and move to the appropriately named Terror Lake, unaware that Bob is making the journey with them, strapped to the bottom of their car. Cape Feare is one of my favourite episodes because in spite of all the wonderful movie references, it’s some of the throwaway jokes that you may have missed the first time, like Homer’s ill-conceived “Witness Protection Programme” t-shirt, or the sign outside Springfield Penitentiary that proudly reads “America’s Fastest Growing Prison!” that get the biggest laughs. No other show rewards the eagle-eyed viewer quite like The Simpsons, and thanks to the gloriously-produced DVD box-sets you can revisit classics like Cape Feare again and again, hopefully each time spotting something new.

Best Bit:

Lawyer: Robert, if released, would you pose any threat to one Bart Simpson?

Sideshow Bob: [faking innocence] Bart Simpson? [chuckles] The spirited little scamp who twice foiled my evil schemes and [maliciously] sent me to this dank, urine-soaked hellhole? 

Officer: Uh, we object to the term, "urine-soaked hellhole," when you could have said, "peepee-soaked heckhole." 

Sideshow Bob: Cheerfully withdrawn. 

Lawyer: But what about that tattoo on your chest? Doesn't it say, "Die, Bart, Die"? 

Sideshow Bob: (conciliatorily) No, that's German for "The, Bart, The." 

[The spectators laugh] 

Officer: No one who speaks German could be an evil man! 

Judge: Parole granted.

6. Lisa On Ice

Another aspect of The Simpsons that makes me cherish it so much, and marks it out from other, inferior, American cartoons (Family Guy, American Dad, and, to a lesser extent, South Park) is the emphasis placed on female characters. In what is traditionally a male-dominated and male-orientated industry, it is refreshing that one of the most beloved, and certainly the most intelligent characters is an eight-year-old girl. Lisa Simpson is a truly remarkable individual, yet in spite of all the marvellous and admirable things she has done in her short life (creating a feminist doll to rival the sexist Malibu Stacy figurine, becoming the youngest ever member of the Springfield chapter of MENSA) it is an episode that highlights the baser aspects of her personality, or her more “Simpson” side that I have chosen to single out. After an F in gym class threatens her with academic failure for the very first time, Lisa, in an attempt to salvage the grade, joins an out-of-school team and discovers a natural ability at Hockey. Soon she is the star player of Apu’s “Kwik-E-Mart Gougers”, but alas, all is not well. Used to being overshadowed intellectually by his brighter sister, Bart has never been eclipsed by her athletically before and reacts badly. The intense sibling rivalry is pushed even further by their father’s constant goading, and pretty soon the whole town is obsessed with the outcome of the impending fixture between their two teams, with even Moe the bartender stopping by at dinner to try and ascertain any information “that may have been kept from the gambling community.” Lisa, who so often represents the moral centre of the show, for the first time reveals a truly dark side; wearing the dismembered head of Bart’s treasured childhood toy Mr Honey-Bunny round her neck for good luck, and encouraging her team mates to “hack the bone” when Ralph Wiggum loses a shin guard. With four seconds to go in a tie game, Bart faces his sister with a penalty shot, yet is the male Simpson child who saves the day with an act of solidarity and love towards his younger sister. Marge is overcome with pride, Homer starts to weep with shame, and like all good episodes it finishes with a riot, this one instigated by Chief of Police Clancy Wiggum.

Best bit:

Marge: (flicking light switch on and off to stop the children fighting) Stop it! Stop it! Stop it! 

Bart: Mom, that is really annoying!

Lisa: Bart started it.

Bart: Uh uh, Lisa started it.

Marge: I don't care who started it. I don't ever want to see you two fighting like that ever again. We love you both: you're not in competition with each other. Repeat: you are not in competition with each other.

Homer: (running in) Hey! Apu just called. This Friday, Lisa's team is playing Bart's team. You'll be in direct competition! And I don't want you to go easy on each other just because you're brother and sister. I want to see you both fighting for your parents' love! Fight! Fight! Fight! Fight! (Starts flicking light on and off).

7. $pringfield (Or How I Learned To Stop Worrying And Love Legalised Gambling)

Despite the insanity of most episodes, The Simpsons does paint a fairly traditional and even conservative picture of American life. For all his failings, Homer is a diligent and loving husband and father, and Marge is a truly wonderful mother. Like most families (or certainly in my own) she is the glue that keeps everyone else together, so it is hardly surprising that the closest the family has ever come to catastrophe is when Marge is either away, or pre-occupied. With the local economy close to ruin, a suggestion by Principal Skinner at a town meeting to legalize gambling is immediately approved, and never one to miss an opportunity (“By building a casino, I could tighten my stranglehold on this dismal town!”) Burns opens a casino with “sex appeal and a catchy name” calling it “Mr Burns Casino”. Initially everyone seems to benefit from it’s opening, Homer gets a job as a blackjack dealer, Bart converts his tree-house into a rival, complete with Robert Goulet performing “Jingle Bells, Batman Smells” and “alternative” gambling (bets can be placed on the following: Mrs Krabappel nervous breakdown: 2-1, Fat kid popular: 50-1, Bart gets his own TV show: 1000-1) but when Marge develops an addiction to gambling, the very fabric that holds the Simpsons together is almost ripped apart. When Lisa has a nightmare about the Boogeyman Homer nails the windows and doors shut, and lies in wait for him, shotgun in hand. The suffering family reaches their depths of despair when Lisa elicits her father’s help with designing her Florida costume for a school geography pageant. Homer’s handiwork is so atrocious that she receives a special award for “Children Who Received Absolutely No Help From Their Parents”. Her humiliation over the incident is enough to make Homer finally confront Marge about her problem (“You promised Lisa you’d help her with her costume. You made her cry. Then I cried. Then Maggie laughed...she's such a little trooper!”) and soon enough the family is back to normal, with their loving matriarch restored to her rightful place.

Best bit:

Lisa: I’m not a state, I’m a monster!

Homer: No Lisa. The only monster here is the gambling monster that has enslaved your mother! I call him Gamblor and its time to snatch your mother from his neon claws!

8. Mother Simpson

And now we move seamlessly from (almost) ever-present Mothers to absent ones. More so than any other character, Homer sees to have gone through the whole-range of human emotions, sometimes within the space of a few minutes. Being as insatiably impulsive as he is would clarify this phenomenon, but the one emotion we rarely see on his part is genuine sadness. This is what makes Mother Simpson such a unique and special episode, as for the very first time in the shows history we are exposed to a vulnerable side of Homer that makes us love him all the more. After successfully faking his own death to get out of working on a Saturday, he is reunited with his long-lost mother, a hippy activist who was forced to flee Springfield in the sixties after destroying Mr Burns’ chemical warfare lab. Her arrival reawakens the child in Homer, while Lisa finally manages to understand where her intellectual curiosity originated and bonds with her immediately (“You didn’t dumb it down! You said rapport!”). Trouble is in store though, for after being spotted at the Post Office by Burns, Mother Simpson is again forced to flee Springfield, and Homer’s reunion with the parent he had lost for 27 years is all too brief and fleeting. The episodes conclusion is far and away the most profound moment in the shows illustrious history, even more so than And Maggie Makes Three. Homer, having said a tearful goodbye to his mother (“At least I’m awake for your goodbye this time”), delays going home to his family and decides to sit on the hood of his car watching the stars instead. Like all episodes included here, it contains the three criteria that constitute the best of what the show has to offer: genuine emotion, good jokes and a great story. The less said about the two hideous sequels, My Mother The Carjacker, and Mona Leaves-a, the better. If anything highlights the difference between the Golden Age of the show, or the shockingly unfunny gag-fest it has mutated into now it is these two episodes. Someone, somewhere, made the ill-fated decision of turning America’s best TV show into a cartoon. Idiots. 

Best Bit

Mr. Burns: I'd like to send this to the Prussian consulate in Siam by aeromail. Am I too late for the 4:30 auto-gyro?

9. Homer The Vigilante

After a string of cat burglaries terrorise the residents of Springfield, justice is demanded but Chief Wiggum and his inept police force are unable to assuage anyone’s fears, and so a vigilante group is formed, which Homer is misguidedly elected to lead (“We don’t need a thinker. We need a doer! Someone who’ll act without considering the consequences!”) Things start well enough as his “drunken posse” cuts down on minor crimes like leaf-burning, but with violent sack beatings up 400% (“I’d be lying if I said my men weren’t committing any crimes”) and no end to the string of burglaries, it becomes obvious that the influence he now wields has gone to Homer’s head, and so when the towns pride and joy, the World’s largest Cubic Zirconia is stolen from the Springfield Museum with him asleep at the switch, he is stripped of his title. It is left for Grandpa to finally catch the burglar, and strike a blow for senior citizens everywhere (“Dad, you've done a lot of great things, but you're an old man now, and old people are useless”), but the true magnificence of Homer The Vigilante, coming as it did smack bang in the middle of the Golden Age, is the surrealistic edge that so much of the comedy has. Once you’ve spent years developing characters in as much detail as the Simpsons writing staff did, people will be more than willing to follow you wherever you wish to take them, no matter how fantastic it may seem at first, or how ridiculous some of the dialogue may look on paper. From another infamous on-air Kent Brockman declaration (“Professor, without knowing precisely what the danger is, would you say it's time for our viewers to crack each other's heads open and feast on the goo inside?), to Homer replacing his daughters saxophone with a jug (“Lisa, never, ever stop in the middle of a hoedown!), from Mayor Quimby delivering his monthly kickback to Chief Wiggum while he is in the middle of a lecture on law and order (“You just, you couldn’t have picked a worse time”) to Nelson calling up Bart to mock the fact that the burglar stole his stamp collection (how could he have possibly heard the prior conversation that took place?), like all classic episodes, Homer The Vigilante gleefully blurs the line between fiction and reality, then reverses over it and sets it on fire.

Best bit:

Homer: So I said to him, "Look, buddy, your car was upside down when we got here. And as for your Grandma, she shouldn't have mouthed off like that!" 

Lisa: Dad, don't you see you're abusing your power like all vigilantes? I mean, if you're the police, who will police the police? 

Homer: I dunno. Coast Guard? 

Marge: Homer, wasn't the whole point to catch the Cat Burglar? 

Lisa: And I still don't have my saxophone. 

Homer: Lisa, the mob is working on getting your saxophone back. But we've also expanded into other important areas. [reads a list] Literacy programs, preserving our beloved covered bridges, world domination.

Lisa: World domination? 

Homer: Oh ho, heh, that might be a typo. 

Homer's Brain: Mental note: the girl knows too much.

10. Who Shot Mr Burns (Parts 1 and 2)

Technically I’ve cheated by including the only two-part Simpsons episode to date as a single entry, but they represent such a monumental achievement, for two distinctly different reasons, that to not include them would have been madness. The elementary school strikes oil, only to have it stolen from them by Burns, one of a series of truly Machiavellian deeds he wages against the town and it’s people, the culmination of which is the erection of a sun-blocking device, leaving Springfield completely dependent on Burns Brand electricity. Part 1 finishes with Burns having been shot, and the whole of the disgruntled town as potential suspects. If Part 1 is all about developing tension (which it does remarkably, the ominous sounds of Burns’ drilling company going about his dastardly work makes this almost a pre-cursor to There Will Be Blood) then Part 2 is about unravelling the numerous loose ends and solving the crime, in a manner of which Raymond Chandler would be proud. Like all great mysteries, all the clues are up there on-screen for you making it a genuine whodunit, and while it is impossible to relive the joy of seeing it for the first time, this still holds up to repeated viewings by virtue of how many red herrings are subtly hidden away (my personal favourite, just before entering Burns's office to spray paint his name, Homer stands in front of a sign that says "IN ONLY", but his head blocks all of the letters except "NO", and a small arrow can be seen pointing at him). Part 1 is possibly the most intense Simpsons ever produced, while Part 2 contains more MacGuffins than Hitchcock at his best.

Best Bit:

At the town meeting, where all the people wronged by Burns have gathered to vent their anger.] 

Mayor Quimby: All right, settle down, people. We are all upset by Mr. Burns' plan to block out our sun. It is time for decisive action! I have here a polite but firm letter to Mr. Burns' underlings who, with some cajoling, will pass it along to him or at least give him the gist of it-- 

Mayor's Bodyguard: (whispering) Sir, a lot of people are stroking guns... 

Mayor Quimby: Also, it has been brought to my attention that a number of you are stroking guns. Therefore I will step aside and open up the floor.

Matthew Kleebauer