Top Ten Characters from 20 Years of The Simpsons: Part One


With The Simpsons’ 20-year anniversary having been on December 18th, you would think that I would make two top 10 lists, but alas my list formats were made to be followed and ten is still a perfectly cromulent number.  After all, being 20 years old isn’t what makes The Simpsons great, its many instances of greatness do.  Of those there are surely more than twenty.  While other soft news locales are writing impacting diatribes about the show’s lasting effects on a generation, I want to take it another direction and celebrate those who have helped our beloved farce of an American family reach this milestone.  Part One of my top 10 will consist of characters 10-6, with Part Two concluding after the holidays.

Watching The Simpsons you come to love the iconic and dysfunctional family, but you also come to love Springfield, from the Tire Dump to the Nuclear Power Plant.  A cast of well-over 100 supporting characters was born in this town, a great many of which helped carry the comedy load while the show successfully bridged four decades.  From the exhausted staff under Principal Seymour Skinner at Springfield Elementary to the grossly inadequate police forces of Chief Clancy Wiggum, Groening and company concocted a bevy of characters so fantastic they can dominate a joke, a scene, or even an entire episode.  Here are the top 10 neighbourhood characters from 20 years of The Simpsons and the episodes that made them great (if I forget your favourite, *annoyed grunt*) :

Lovejoy110. Reverend Lovejoy: Reverend Lovejoy is one of those underrated characters that is consistently brilliant.  It would be really easy and lazy for The Simpsons to make Lovejoy the polar opposite of what a minister should be, some sort of alcoholic womanizer or something, but instead they take a subtler approach to his satire.  He is a devout man of faith, yet he is terribly exhausted by the weight of his own church – shown both in his uniformly boring sermons and his apathetic dealings with Ned Flanders.  Thus, whenever he skirts the line on morality, it is much funnier than if he was simply the worst man for the job.  It makes his reaction to his daughter Jessica’s rebellion (“Well, come on! Use your imaginations!”) and the impending doom of the Bart Comet (“It’s all over, people! We haven’t got a prayer!”) all the more effective.

Bart sells his soul for funny-smelling sponges.

Best Episode – Bart Sells His Soul: The reverend is only really a main character in one episode, “In Marge We Trust,” but Lovejoy really shines brightest in his role uncovering Bart’s prank, switching the choral music and killing the church organist.  Vintage Lovejoy:

LOVEJOY: “Wait a minute.  This sounds like rock and or roll.”

LOVEJOY: “And now please rise for our opening hymn, ‘In the Garden of Eden’ by I. Ron Butterfly.”

LOVEJOY: “Milhouse, you did the right thing by telling me.  Bart, come with me for punishment… you too, snitchy.”

troy_mcclure9. Troy McClure: Let’s just start with a list of titles: Here Comes the Coast Guard, Dial M for Murderousness, The Erotic Adventures of Hercules, The Boatjacking of Supership 79, The President’s Neck is Missing!, Leper in the Backfield, Hydro – the Man With Hydraulic Arms, and, of course, The Contrabulous Fabtraption of Professor Horatio Hufnagel. Who among you would not see these Troy McClure “classics” if they actually existed?  Having been seen in everything under the sun, Phil Hartman’s sell-out schmaltz of an actor Troy McClure is a great character for both movie parodies and home shopping atrocities.  I mean, this is the guy who points out that until now the best way to get juice out of an orange is to crush it against your forehead.  He makes the list because his shtick remains fresh.  Each self-introduction brings a new pair of ridiculous titles without the viewer feeling like the show is bombarding you (with Bible questions!) with the character’s gimmicky catch phrase.


Planet of the Apes: The Musical

Best Episode – A Fish Called Selma:  I don’t think this is much of a surprise, as it features a cavalcade of hilarious faux movie titles and a plot rife with Hollywood phoniness.  Not to mention Planet of the Apes: The Musical.  Vintage Troy:

TROY: “That’s right, boys, Troy’s back from the gutter and he’s brought someone with him.”

TROY: “Hello, Selma Bouvier.  You might remember me from such dates as last night’s dinner.”

WAITER: “Cigarette, Mrs. McClure?”
TROY: “You bet.  From now on, she’s smoking for two.”

drnick8. Dr. Nick Riviera: Another character with an amazingly infectious quotability is Hollywood Upstairs Medical College graduate Dr. Nick.  Though rare to be seen in later episodes of the show, for a few seasons during the golden age of The Simpsons they didn’t need Dr. Hibbert – they had his unqualified Hispanic equivalent.  Incompetence is a great tool for comedy, but it is especially poignant in Nick because of the importance of his profession.  It is also notable that Dr. Nick is basically the town malnutritionist.  In addition to his juicer which comes with laxative sun tan lotion, he helps Homer reach 300 pounds in “King-Size Homer” by providing details on the neglected food groups and non-toxic play doughs.  Dr. Nick is on the list because his character allowed the writers to include a plethora of dark and morbid jokes about America’s health care system or lack thereof.

You are highly skilled... at goofing off!
You are highly skilled... at goofing off!

Best Episode – Homer’s Triple By-pass: An episode about Homer undergoing major surgery is serious enough as far as Simpsons episodes go, but when you add Nick to the equation it becomes both funnier and more intense – particularly when Homer’s insides get stuck to his wristwatch.  Vintage Nick:

Dr. NICK: “Call 1-600-DOCTORB… the B is for ‘bargain!’”

Dr. NICK: “Oh, no. Blood!  They didn’t tell me about this in medical school. (tape fuzzes into People Who Look Like Things)  Oh, no, someone taped over the end of this.”

Dr. NICK: “The coroner?  I’m so sick of that guy.  Well, see you in the operating place.”
REPORTER (scrumming): “Where are the bodies?”
Dr. NICK: “Such a beautiful day.  I think I’ll go out the window.”

milhouse_17. Milhouse Van Houten: Bart’s nerdy best friend Milhouse has been through a lot and has a hard road ahead of him if episodes like “Lisa’s Wedding” prophesied truly.  He’s gotten pummeled as goaltender for the Kwik-E-Mart Gougers, his parents got a divorce in season 8, and he has even spent an episode being chased by the FBI (“Oh, no, not again!”) in “Lisa’s Rival.”  Milhouse has the incredible use of being both Bart’s weak and pathetic friend and a surprisingly tender soul.  For example, we often see Milhouse cry – like when he does long division and has a remainder left over or when Itchy & Scratchy take too long to get to the fireworks factory – but we also have moments where he exhibits a poetic soul, such as when two doves cry in “Lemon of Troy” or  his slow suffering as Fallout Boy in “Radioactive Man.”  Despite all this, I can’t help but think his best moment was getting whacked in the head by the mike of Robert Goulet in “$pringfield.”

You guys wanna see something gross?
You guys wanna see something gross?

Best Episode – Bart’s Friend Falls in Love: The magic 8-ball might have seen this coming.  Samantha Stanky’s arrival in class sets Milhouse and Bart apart and the result ain’t pretty.  The comedy and transition in Milhouse’s character throughout, though, is.  Vintage Van Houten:

MILHOUSE: “How could this happen?  We started out like Romeo and Juliet, but it ended up in tragedy.”

MILHOUSE: “I went to Circus of Values and bought you a ten-gallon tub of Gummi Bears.”


MILHOUSE: “Let me try.  Will I get beaten up today?” (8-ball: all signs point to yes).
NELSON: “That ball knows everything.” (clobbers Milhouse)

SideshowBob26. Sideshow Bob Underdunk-Terwilliger: Though crude and but a cardboard cut-out of his later self for a few seasons, Sideshow Bob truly developed into a very funny and very useful character – which is likely why in later seasons the writers kept coming back to him.  Though he has his share of the comedy load (see: physical comedy – rakes to the face), Bob also adds danger, mystery, and malevolence to any given episode.  Not to mention crisp linguistic phrasings and high-brow pontificating.  Compare this to other guest characters – even main characters – and you can see what a joy Sideshow Bob must be to write.  A lot of menace, a touch of buffoon, and an inescapable fate of having his chances dashed at the last moment, no matter how clever the plot, makes for involved story telling and an involving antagonist.  It must be mentioned that Kelsey Grammer deserves a whole lot of credit for his voice work, because in addition to hopping from articulate to diabolical, sometimes in the same sentence, his take at Frasier likely influenced the decision to let Bob transform into a scholarly dissident waxing poetic.

Bart wanna see my new chainsaw and hockey mask!?!?!
Wanna see my new chainsaw and hockey mask!?!?

Best Episode – Cape Feare: I am a fan of most Sideshow Bob-driven episodes, but his return in season 5 is certainly the most terrifying.  Fitting, since the Simpsons move to Terror Lake.  Or should I say the Thompsons?  The cactus patch scene gets me every time.  Vintage Sideshow Bob:

SIDESHOW BOB: “Oh, I’ll stay away from your son all right.  Stay away… FOREVER.”

SIDESHOW BOB: “Very well, Bart.  I will send you to heaven before I send you to hell.”

SIDESHOW BOB: “No, that’s German for ‘The Bart, The.’”
PAROLE BOARD MEMBER: “No one who speaks German could be an evil man.”

*Part 2, featuring characters 5-1, to come after the holidays.  Any guesses as to who they could be?*


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