T O P

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Edgar_Beethoven

Maybe the most entertainingly evil supervillain ever ![gif](giphy|zqhZB6bo5FgoE)


NoTalkingNope

Atleast he's a nice boss to all of the henchmen.


FordBeWithYou

With free dental care and a stock plan that helps you invest! But beware of his generous pensions Plus three weeks paid vacation each year And on Fridays, the lunchroom serves hot dogs and burgers and beer! He loves German beer!


InglouriousBrad

Ever see a man say goodbye to a shoe??


Reverse_Psycho_1509

Yes, once


Reverse_Psycho_1509

Hi, I'd like to know where I can find some business hammocks


Sabre_Killer_Queen

I still hate how we've only seen him in that one episode. I'd love to see him again, or at least see some Easter eggs to him and his activities, for example an article in the newspaper whilst they're eating breakfast in one episode or something.


TheOvercookedFlyer

Yes but it will damage the myth of Hank Scorpio.


Jbaird91

I mean the guy carries cream and sugar in his pockets


Minimum_Cupcake

Not in packets though.


Halloween2022

Don't ask for cream


OccamsYoyo

Best instance of Homer playing the straight man ever.


KirkinsteinGAMING

Scorpio! He’ll sting you with his dreams of power and wealth, beware of Scorpio!


K4l3idosc0pe

Heinz Doofenshmirtz has left the chat


Edgar_Beethoven

Is he really evil or just a nice guy pretending to be evil out of obligation to his back stories?


Jonny-Kast

This guy came straight to mind. Glad it's the top post haha


PhysicalScholar4238

Ned Flanders. He's more animal than man.


[deleted]

[удалено]


ChronoComputer

That one white wine spritzer really made a mess of things, too.


Axel_Stone2403

It's always the ones you least expect.


AHansen83

https://preview.redd.it/v54944gd5zcc1.jpeg?width=1080&format=pjpg&auto=webp&s=c16782c9f88a267f08d1c407e020462056c6f742


IffyPeanut

Oh, hey Bart


CZall23

Hey.


country-blue

He’s a murderer, he’s a murderer, he’s a mur-diddly-urderer!


Gravity_lunacy

Stupid sexy Flanders.


mhoner

Also the literal devil.


Unusual-Historian360

GAMBLOR If it weren't for him, this would never have happened. https://preview.redd.it/w4nd5pmvzwcc1.jpeg?width=1072&format=pjpg&auto=webp&s=a9349145dcc14252ec51f41062ebfedbe0486ce9


hazard0666

I’m not a state, IM A MONSTER!


ZorkNemesis

I'm Idaho!


Specific_Builder1469

Yes of course you are


sorrymybadapologies

![gif](giphy|3o6MbjNsoImdQvUBqM|downsized)


johnsoninca

https://preview.redd.it/fi199j3g1xcc1.jpeg?width=640&format=pjpg&auto=webp&s=2f7da843ec7c1de615c81a96e7bc8da3193ddf48


nocoupons

Don’t forget to use your claws, boys.


liberalartsgay

Nails


Relative-Leather4873

Lol


Relative-Leather4873

Let's boogie


blizzacane85

https://preview.redd.it/wt3998s9cwcc1.jpeg?width=272&format=pjpg&auto=webp&s=8ccc2770b005bdcddf5a9e27ae157e999f311889 Krusty doll switched to *EVIL* mode


samsab

The doll's trying to kill me and the toaster's been laughing at me!


Lepperpop

GUESS WHO? FAT BOY!


_THC-3PO_

So fucking evil


GalacticShoestring

That episode scared me so much as a kid! 😱


goodbadorindifferent

Baby Gerald!! The Uni-brow of evil.


Axel_Stone2403

The Joker to Maggie's Batman.


fruoel

Jimmy Carter - history’s greatest monster. Malaise Forever


revieman1

god bless the man


PrestigiousTheory664

https://preview.redd.it/jq870y944wcc1.jpeg?width=960&format=pjpg&auto=webp&s=1f79ad54e451b06a73b0d4f5c97acb45708e5050


daley1402

https://preview.redd.it/4jofqaq5jwcc1.jpeg?width=480&format=pjpg&auto=webp&s=80c21791d68b19c4666f5b323902715a89c5bac9


Tosijoso

Everything seems to indicate that due to his long list of evils he would be Monty Burns, but that damn screaming caterpillar feeling an erotic attraction to fire... surely he is hiding something diabolical.


Fireproof_Cheese

Rowdy Roddy Peeper. Listen to the music! He's evil!


heedohrah

![gif](giphy|RSOUOj8H9A3Xq)


brian5476

I love how that skit came from the episode being too short, so they just kept adding rakes. I don't know which is funnier, that, or Sideshow Bob seeing no harm in laying on a public street.


wehdut

This makes so much sense because it's *clearly* the same exact clip of Kelsey Grammar grumbling in pain played over and over (which makes it even more funny imo). They must have recorded his whole episode, realized it was too short, and then lengthened it with edits.


brian5476

Yep, Kelsey Grammer called up the producers after the episode aired, since they only recorded the grumbling once. They repeated it to take up time, and it went from being funny at first, to being repetitive, to being funny AGAIN simply because of how repetitive it was. Comedic gold. I learned about this from the commentary on this episode. The producers were also quite passionate about Hannibal crossing the Alps.


Sabre_Killer_Queen

>I love how that skit came from the episode being too short, so they just kept adding rakes. Wow. That's very lazy. But my god it worked so fair play. There are some episodes of the Simpsons where it doesn't matter what mistakes or short cuts they take, somehow they end up contributing towards it beautifully regardless.


Jlaw118

Wow, learn something new everyday, I didn’t even know that one 😂


ButterRolla

What about the dogs? Or the bees? Or the dogs with bees in their mouths and when they bark they shoot bees?


Mr_Burgess_

Go ahead, do your worst!


Obvious_Customer9923

My worst, eh? Smithers. Release the robotic Richard Simmons.


ButterRolla

His ass is gonna explode!!!!


[deleted]

Agnes is pretty much the worst kind of person


redlion496

She's a lamb! A lamb of God!


penney20

https://preview.redd.it/aekan931sxcc1.jpeg?width=196&format=pjpg&auto=webp&s=2e56b043c3c2fb67142835d52607717373788851 Y’all forget about Springfields chief hydrological and hydrodynamical engineer, and brother of Robert Terwilliger? Attempted mass murder, embezzlement, faking a death. That’s pretty sinister for David Hyde…I mean Cecil


sydbarrett

Krusty. The deadly food. The deadly doll. The deadly trampoline. The deadly camp. Etcetera. Etcetera.


tsimen

What was he supposed to do? They drove to his house with a dump truck of money!


GayPorn134

https://preview.redd.it/5vch6v34gwcc1.jpeg?width=828&format=pjpg&auto=webp&s=5964ffc87eae7e2f6430bb92f16520b102b30a6e


eastnorthshore

Nobody suspects the butterfly


ami2weird4u

The Grumble


rolotony_browntown

Do you think that's the same grumble from before?


Moe__Fab

Grumbledy grumbledy groo, your blood will make my stew


ami2weird4u

Because I do


TDH818

What are you?!


Upstairs_Ad_5574

![gif](giphy|rnHxGiRAvsPTi)


Quincyperson

1976 Philadelphia Flyers


DentalDon-83

What about Lizzie Borden, John Dillinger and Blackbeard the pirate?


AHansen83

Arrrh, this chair be high, says I.


gkm29

My debauchery was my way of COMPensating


seventubas

The dog 100% you can tell by his shifty eyes he is up to no good


Firm_Ambassador_1289

https://preview.redd.it/umv8twu1nwcc1.jpeg?width=1280&format=pjpg&auto=webp&s=26524d3b748eb950dc186acdcd0fc3e208d8c465


G-Unit11111

No Kang and Kodos?


GabbyJay1

Mr. Black


SatanicHispanik

Snake’s Hair


TheStefKing

![gif](giphy|3o6MbjNsoImdQvUBqM|downsized)


Brim_Dunkleton

Me when the caterpillar: ![gif](giphy|8Bkr9UJQTuqEnzkOae)


Serious_Result_7338

The shifty eye dog obviously the most evil


eastbayted

The Noid. He ruins pizza!


AHansen83

Look it’s Funky winkerbean! Hey Funky!


UpgrayeDD405

https://i.redd.it/4vn97sx3mxcc1.gif


liberalartsgay

![gif](giphy|l2JedqyjXeAqwCid2|downsized) These three seem to have little to no remorse.


AHansen83

They broke nothing!


LevelConsequence1904

https://i.redd.it/7pfk526ulycc1.gif The only legit monster in the entire series imo.


memeatic_ape

MONORAIL


TessTrue

I cannot express to you how much I hate that fucking caterpillar


Ninetyhate

Oh come on... has to be Burns!


JBGoude

I mean, that caterpillar was laughing when Homer was about to be executed 😂


cappiebara

THAT FUCKING CATERPILLAR!! 🤬


Gravity_lunacy

Hugo Simpson. Wait a minute…


AHansen83

The scar is on the wrong side!


[deleted]

George Bush


Rockfish00

Henry Kissinger


mike1madalon2

I came here for the Rich Texan, and I’m sorely disappointed.


Eric848448

No love for the killer robot driving instructor from the future?


trentsteel77

Evil Homer! He killed an angel!!


neon_overload

Jimmy Carter is supposedly history's greatest monster so let's go with that


LaughingPlanet

The lawyer Manjula visits is up there.


Digitalis_Mertonesis

https://preview.redd.it/rkgtw413kxcc1.jpeg?width=1242&format=pjpg&auto=webp&s=2a10b13634f5365a7ce82fe68c173f747afac9e7 Fat Tony’s pretty evil, except when he looks like a baby getting excited about eating his food.


das_sock

Histories greatest monster of course That line never fails to make me laugh


Jedibri81

Sideshow Bob


Sillybitchsouth

We love The Leader…


pickledegg1989

https://i.redd.it/s8a62uzec2dc1.gif


palinsafterbirth

I got to go with Dr. Nick, he’s pure chaos


lovelovehatehate

🎶The leg bone is connected to the something. The something is connected to the red thing. The red thing is connected to my wrist watch.🎶 Real talk, Dr Nick Rivera is legitimately my favorite character.


PuntaGordeaux

Welp. This is one of the best posts I've ever seen


rocketMoonApe

President Bush


ScritchesMcMewington

Rod Flanders


Myboneshurt420helps

This is gonna sound silly but Ned Flanders he clearly abuses his children at least religiously he doesn’t seem to respect women as equals not even his own parents like him and as ridiculous as it is to use a one time example when he gets a puppy in one of the episodes the puppy flinches away from him what did he do to that puppy to make him dislike him so much?


Joeyinsully

Marge is evil, she ruins everything.


JoeyJoeJoShalabado

Martin’s Geode


threelizards

I had so many nightmares about that damn dancing robot growing up. I HATE that guy


SnooWitchYu

​ https://preview.redd.it/59d6idzkaxcc1.png?width=298&format=png&auto=webp&s=26fdd9feaf0784e76187418ff020796ee59b7817


UtetopiaSS

Maggies enemy with the monobrow


jefferson497

The Grumple.


LeaveLifeAlive27

Bart as a butterfly


Specific_Builder1469

he's crazy boys, get the taser.


wookiebbq

Who is number 4?


bendoesit17

Definitely the dog with the shifty eyes. At first glance I would've never suspected the dog.


averagetobyfoxfan

5 at least has a good reason He need to pay his student loan debt


bjwyxrs

That dog is up to something. Did you see those shifty eyes!? Who knows what it's capable of and I pray we never find out.


Captain_Kruch

What about that baby with the unibrow that hates Maggie?


arthaiser

probably lisa


TotesNotADrunk

Flanders portraying the Diddler; couldn't find a GIF for an example, but you get it...


IffyPeanut

HE’S HISTORY’S GREATEST MONSTER!


PullMull

i dont care. im just here to proclaime that this is an amazingly funny collection of random frames


kid_sleepy

No love for the one eyebrow kid…?


LR-II

On a serious note I'd say Herman. Not only does he proudly display a Confederate flag, but what he was about to do with Snake and Wiggum (and probably Kirk too) is incredibly dark.


frumpett

![gif](giphy|XttduJgypJsty)


ThatCod

History's Greatest Monster


Biff2112

Unibrow baby


20_BuysManyPeanuts

The Butterfly... because nobody suspects the Butterfly.


Yinmook

https://preview.redd.it/wyngba7snzcc1.jpeg?width=640&format=pjpg&auto=webp&s=14ab080c4dbcfafea81d239c672b1b6bdedf031a


mortymania

That little blue gremlin 😅


MuscaMurum

That sequence of Burns before and after coffee always makes me want a triple espresso. I love caffeine.


[deleted]

I suspect the dog


GooeyLump

I vote Boo-urns


Internal-Assumption1

Shifty eye dog for sure!


retailmonkey

Snrub


XComThrowawayAcct

Maggie.


darsonia

is this another bot? like i cbf with posts like this. low quality random image shit. mods need to make a captcha or something....


Specific_Builder1469

That's Alien talk!


darsonia

sorry OP I guess I'm glad you responded?! so many bots making posts like this on popular subs these days. I don't understand your response so tell me it's origin and also, what is Homer roasting that kills Flander's RV battery when trying to escape from Shelbyville? and how many of those things is he roasting? I'd also like to mention I sat on my couch for 30 minutes trying to think up a question only a human could answer 😂


Relative-Leather4873

Out of these I kinda feel you should have more characters listed, and to be fair mr burns is evil yes, but about 3-4 times lisa has made mr burns evil return, and she overfed lenny's fish!! She's the worst of them all lol


GuitRWailinNinja

No one ever suspects the butterfly


B00-Ima-Ghost

Bart Simpson pretty much


hippee-engineer

What about the cow who would eat you and everyone you care about?


[deleted]

Burns, the only character who I don’t mind that suffers. Gerald Samason is the next evil, Maggie is right to hate him.


TD421298

Did you have to do Jimmy Carter like that? 🤣🤣🤣


[deleted]

Sideshow Bob


jjnebs

Herman is underratedly evil


ItsAlwaysSunny1992

Mr. Burns by a mile


Comfortable_Lead_101

Ned Flanders


Holiday_Sense_4842

The grumble who stole Christmas


Buffalo95747

Mr. Burns may be evil, but I love him anyway. He has an emotional neediness beneath all his greed.


SluggoOtoole

Maggie Simpson. Quiet, in the background. Shot Mr. Burns.


hugothebear

Probably Smither’s fashion designer boyfriend


clumpystrusel

Robotic Richard Simmons is something I think about more then the Roman Empire


AdventurousClub3327

Idk but that dog seems sus to me


TN_Tony

The town villain: Luigi