Top Ten Characters From 20 Years of The Simpsons: Part Two


Before the holidays I embarked on the perilous journey of choosing the ten ‘greatest’ Simpsons characters from the show’s last 20 years, not including the principle family itself.  Check selections 10 through 6 out here.  A perfectly cromulent list thus far, if I do say so myself.  The final five are even harder to decide upon because they have to stand above those already mentioned.  No easy task.  Without further ado, here are the Top 10 Simpsons characters part 2, numbers 5 to 1.  I make no apologies this time!  After all, I voted for Kodos.

5. Krusty the Clown: Many original writers’ favorite, Krusty is an even greater schmaltz than Troy McClure – but for entirely different reasons.  He is certainly the worst possible character to be a child’s role model (with the possible exception of Mr. Burns) and a biting take on every Hollywood icon whose behind-the-scenes life is nothing short of pathetic.  Krusty is at his best when he is forgetting who Bart is (another similarity to Burns), selling out and then blowing the money, or tormenting his sideshow performers.  And let us not forget that it is Krusty who brings us the glory that is Itchy & Scratchy.  You know Krusty is a great character when the animators can leave him in his clown makeup and outfit for the entire tenure of the show and yet he fits in perfectly with the rest of a Simpsons mob.  It becomes hard to recognize that at any given time he’s still wearing clown fatigues.  Though no Simpsons character should ever have a spin-off of any kind, Krusty the Clown would be my choice if someone put a gun to my head.  If anyone could get the Red Hot Chili Peppers to change their lyrics, it’s the purveyor of Krusty Home Pregnancy Kits.

Accepting the award is the son of the guy who played Huggy Bear.

Best Episode – Homie the Clown: There are many episodes that feature Krusty prominently, especially his wonderful comeback special featuring a vengeful Bette Midler, but “Homie the Clown” revolves so fully around clowning, with Homer taking on Krusty’s likeness, that pound for pound it has the most “Krusty” moments.  Though Homer grabs a lot of the spotlight, Krusty is in top form getting schmoes to do all the jobs he wouldn’t touch with a ten-foot clown-pole.  Vintage Krusty:

ACCOUNTANT: “Let me get this straight.  You took all the money you made franchising your name and bet it against the Harlem Globetrotters?”
KRUSTY: “I thought the Generals were due!”


KRUSTY: “Hire Kenny G to play for me in the elevator.  My house is dirty, buy me a new one.”

KRUSTY: “Now, when the wealthy dowager comes in, the party’s over, right? Wrong!” (whips a pie that smashes dowager’s face into the wall)
HOMER: “Kill… wealthy… dowager.”

4. Kent Brockman: Kent Brockman may work in broadcast journalist, but a more alarmist name would be “The Killbot Factory.” The face of Channel 6 News and yet another ass from the entertainment industry, for me Kent Brockman is the most underrated character on the show.  He does not have a catch-phrase, there is nothing catchy about his voice or appearance, but upon re-watching he truly has some killer lines.  What’s great about Kent is that most of his material is either high-brow political or social commentary or ridiculous paranoia.  I mean, we’re talking about the guy who asks an expert if it’s time for people to crack each other’s heads open to feast on the goo inside.  Brockman is a further satirical stretch than most other characters on the show.  He is less of a spot-on critique than an aggrandized oaf, and it almost seems as though the writers enjoy making him spew flippant remarks a little too much, but this allows the character to expand into one whose strength comes entirely from his punch-lines.

Well, this reporter was...a little hasty earlier...

Best Episode – Deep Space Homer: HAIL ANTS.  Vintage Brockman:

BROCKMAN: “Ladies and gentlemen, we’ve just lost the picture, but, uh, what we’ve seen speaks for itself.  The Corvair spacecraft has been taken over – “conquered”, if you will – by a master race of giant space ants.  It’s difficult to tell from this vantage point whether they will consume the captive earth men or merely enslave them.  One thing is for certain.  There is no stopping them; the ants will soon be here. And I, for one, welcome our new insect overlords.  I’d like to remind them that as a trusted TV personality, I can be helpful in rounding up others to toil in their underground sugar caves.”

3. Grandpa Simpson: Another sometimes overlooked character is Homer’s befuddled and neglected pop, Abraham Simpson.  I love Grandpa.  If Golden Girls has taught me anything, it is that zany old people are hilarious and Grandpa is about as zany as they come.  Though useful as a sentimental character and story mover, he is better used as a gag character who is there when he needs to be to point out that the government doesn’t control the sky and you could live in a balloon.  Granpda can fill either role because he has been constructed as a bit of a renaissance man.  He has been a Love Tonic swilling man in love (“nope, it’s a stroke”), a former Flying Hellfish union strikebreaker, and even a super-sleuth foiling the car burglar Malloy.  There is not much that you can’t imagine Grandpa not having done.  He’s old.  He canceled Star Trek. He is bound to have picked up some random things here and there over the years – such as a hamburger that could take a bite out of you!

Yo, Mom, we haven't got the eyeballs yet.

Best Episode – Treehouse of Horror III: Gotta mention at least one Treehouse of Horror episode, and Grandpa Simpson delivers some of his best lines at the kids’ Halloween party before telling the story of “King Homer.”  There are numerous more Abe-heavy episodes out there, but I preferred to demonstrate his ability to steal scenes in episodes he is barely in.  Vintage Grandpa:


GRANDPA: “That doll is evil, I tell you. EEEEEEVILLLL!”
MARGE: “Grandpa, you said that about all the presents.”
GRANDPA: “I just want attention.”

BART: “Nice try, Mr. Flanders, but I’ve got a story so scary you’ll wet your pants.”
GRANDPA: “Too late.” (kids all shy away)

MARGE: “Where’d you get all the money?”
GRANDPA: “The government.  I didn’t earn it, I don’t need it, but if they miss one payment, I’ll raise hell.”

2. Lionel Hutz: The unfair passing of Phil Hartman is still one of the saddest moments in Hollywood for me.  There have been a lot more famous people who have died since, but still none have seemed near as important.  A testament to his fine voice acting and unique announcer-esque vaudevillian voice, Hartman makes two appearances on my list with Troy McClure and now Lionel Hutz, attorney at law and expert shoe repair.  Perhaps only having Hutz for earlier seasons of The Simpsons has worked in his favour, but he always delivers, consistently fudging family court appearances or attempts to smooth-talk passing shoppers into purchasing half-drunk Orange Julius.  It is no surprise his first appearance is in the same episode as Dr. Nick, bandaging Bart up to induce a heftier settlement.  Ironically, in something I am sure the writers did not think possible, this is about as competent as Hutz’s legal work gets on the show – that is, if you don’t count the fact he actually knows what ‘contingency’ means on his mixed up sign: “Works on contingency? No, money down!

Ah, ballet.

Best Episode – Marge on the Lam: Hiring a guy rummaging through your garbage as a babysitter is usually an unwise decision, but it allowed us to see Lionel Hutz’s vibrant personality shine.  “Marge on the Lam” is one of the few times that Lionel Hutz is a relevant character outside of the court house or his legal office.  Vintage Hutz:



HUTZ: “Oh, sure, like lawyers work in big skyscrapers and have secretaries.  Look at him!  He’s wearing a belt.  That’s Hollywood for ya.”

HUTZ: “Don’t touch my stuff! Hey, this isn’t the YMCA…”

HUTZ: “Mr. Simpson, I was just going through your garbage, and I couldn’t help overhearing that you need a babysitter. Of course, being a highly-skilled attorney, my fee is $175 an hour.”
HOMER: “We pay eight dollars for the night and you can take two popsicles out of the freezer.”
HUTZ: “Three.”
HOMER: “Two.”
HUTZ: “Okay, two. And I get to keep this old bird cage.”
HOMER: “Done.”
HUTZ: “Still got it.”

1. C. Montgomery Burns: Based on Matt Groening’s math teacher, Mr. Burns is a crooked old man whose name is synonymous with malevolence and whose lifetime of work in the power plant has left him as impotent as a Nevada boxing commissioner.  Mr. Burns wins the coveted top billing for being an unmitigated force of evil in Springfield, and being solely responsible for many major plot elements in some of the very best episodes.  In addition to the “Who Shot Mr. Burns?” episodes at the end of Season 6 and the start of Season 7 – likely the most hyped Simpsons ‘event’ after people doing the Bartman – Burns is also involved in: building a new casino in “$pringfield,” acquiring 25 champion grey hound puppies in “Two Dozen & One Greyhounds,” hiring a team of ringers in “Homer at the Bat,” and even being the alien in “The Springfield Files.”  In fact, more than any other side-character in The Simpsons, Mr. Burns has influenced our principal family’s life: not just for the worst, but for the funniest. He was the one who had the Rolling Stones killed. He was the one who had a missing Brazilian soccer team working his reactor core. He is the one who survives till one million A.D. as a robotic head-in-a-jar.  If Homer is a satirical take on a working-class hero, then Burns is the villain, oppressing his workers, skimping on safety and environmental regulations, and preferring the hands-on touch of hired goons.  While most of the other characters on this list are hilarious in notable scenes, Mr. Burns dominates entire episodes – so much so that it was very difficult to pick an example of when Burns’ star shone the brightest.  Fortunately for you, I am here to bear the brunt of this conundrum.


...the BLURST of times!?

Best Episode – Last Exit to Springfield: Oh, I so desperately wanted to quote Burns Sr. at the Dickensian Atom Smashing Plant!  From Mr. Burns’ attempts to win Homer over to he & Smithers trying to run the planet by themselves, “Last Exit to Springfield” is both a riot and heartfelt victory of good versus Grinch.  Vintage Burns:

BURNS: “This is a thousand monkeys working at a thousand typewriters.  Soon they’ll have written the greatest novel known to man.  Let’s see.  ‘It was the best of times, it was the blurst of times!?’ You stupid monkey!”

BURNS: “Look at them all through the darkness I’m bringing, they’re not sad at all, they’re actually singing.”

BURNS: “Oh, if only we’d listened to that young man instead of walling him up in the abandoned coke oven.”

KENT BROCKMAN: “Now, Mr. Burns, you said you wanted an opening tirade.”
BURNS: “Yes, thank you, Kent.  Fifteen minutes from now, I will wreak a terrible vengeance on this city.  No one will be spared.  NO ONE!”
BROCKMAN: (chuckles) “A chilling portrait of things to come.”

BURNS: “And this is my basement.”
HOMER: “Gee, it’s not as nice as the other rooms.”
BURNS: “Yes, I really should stop ending the tour with it.”

BURNS: “Ah, Homer.  I hope Crusher and Low Blow didn’t hurt you.”
HOMER: “You know, you could have just called me.”
BURNS: “Oh, yes, but the telephone is so impersonal.  I prefer the hands-on touch you only get with hired goons.”

*P.S.: Hank Scorpio didn’t make the list because he’s only in one episode – does not qualify!*

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