- 7/2/2025
From corrupt politicians to criminal masterminds, Springfield has no shortage of memorable antagonists! Join us as we explore the most devious, entertaining, and iconic troublemakers from America's favorite animated family. From petty criminals to corporate tyrants, these baddies have left their mark on the show's legacy.
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00:00You tow me around the track. As we gather speed, I whip you gently.
00:04You state your name and tell me how you got so heavy.
00:06Welcome to WatchMojo, and today we're counting down our picks for the best and most beloved villains of The Simpsons.
00:13Naturally, there will be some spoilers.
00:15Thanks to my team of loopy lawyers, I never have to give you another penny.
00:23Number 20. Mayor Quimby
00:25He's one of the pettier villains, to be sure, but a corrupt politician is still a corrupt politician.
00:31Joe Quimby is mayor of Springfield. A politician so corrupt, his seal is literally corruptus and extremus.
00:38Very well. If that is the way the winds are blowing, let no one say I don't also blow.
00:45Apart from his numerous illegitimate children and his easy acceptance of bribes, Quimby also shows contempt for his constituents.
00:52He can't even hold his own in a debate against the likes of Sideshow Bob.
00:56What is your question?
00:57My question's about the budget, sir.
00:59Oh.
01:00But in the end, even when the citizens finally take over, he is still a fixture of Springfield.
01:06And to think, he is a parody of Ted Kennedy and the Kennedy family in general. Ouch.
01:11Very well. I promise swift and decisive action against these hibernating hucksters.
01:16Number 19. Tab Spangler
01:20Sometimes villains are so vivid and full of life, they are memorable even if they only appear in an episode or two.
01:26When Bart gets unhealthily fat and has a heart attack, his family sends him to Serenity Ranch Fat Camp.
01:32Guess how old I am. Come on, take a guess.
01:3547?
01:36I hate when they're over.
01:39Even on the nose hurts!
01:40Its head counselor, Tab Spangler, is determined to get the campers to lose weight with tough luck.
01:45Spangler is a jerk with a short temper and openly bigoted towards plus-size people.
01:50As you scoop your ice cream into the trash, tell it you hate it! Talk to it!
01:54You think I look like what? What's the vanilla saying? No, I'm not that old!
01:59He is also hypocritical, willing to break his no-fast-food diet for a bite of Homer's cheeseburger.
02:05What an entertaining scoundrel.
02:07What are you eating now?
02:08Cheeseburger.
02:08You're a catastrophe! Let me have half of it.
02:12Number 18. Jack Crowley
02:13Criminal or not, this villain is an artist.
02:17Crowley was sent to prison for shooting Apu, but his down-to-earth politesse and his phenomenal painting skills gave him a second chance at redemption.
02:25Advocated by a sympathetic Marge, he's released.
02:27The prisoner is hereby paroled into your custody.
02:31Oh my goodness!
02:34I'm free?
02:35Oh, Mrs.
02:35Oh, geez, I'm sorry. Sorry.
02:39When Principal Skinner hired him to do a mural, however, Crowley's artistic vision and Skinner's did not align at all.
02:46I followed your napkin.
02:49No napkin could wipe the crumbs of failure from your mouth.
02:53Don't fight!
02:54Enraged at the poor reception of his mural and being given the blame for it, Crowley burns it all down.
02:59He also burns down Skinner's car for good measure.
03:02So much for redemption.
03:03But he's a villain you don't forget easily.
03:06Puma pride! Puma pride!
03:09Ah! Ha ha ha ha!
03:10Catch the fever, Skinner!
03:12Ah ha ha ha ha ha!
03:14Number 17. Goose Gladwell
03:16Bart discovers a world of pure imagination when he meets this Willy Wonka send-up.
03:21After Bart's t-shirt business is shut down, Goose Gladwell offers to sell the shirts at his shop.
03:26But Gladwell's dark side rears its ugly head when he sells the rights to Bart's shirts to the biggest baddie of them all, Disney.
03:32I have sold the rights to the Bart Simpson t-shirt line.
03:36Oh!
03:37To the Disney company, which will turn each one into a movie.
03:41Really? How much money do I get?
03:43You get nothing.
03:44And of course, Bart doesn't get a penny from the sales.
03:47He was Homer of all people who managed to talk some sense into this quirky trickster.
03:51If I turn this dial, the resulting blast would destroy the entire Tri-City area,
03:57including that guy who sells those blue blocker sunglasses people sometimes wear.
04:03Gladwell was given a green beret in Vietnam, which does explain everything.
04:07Never trust a weirdo!
04:10Ah, zoot!
04:12Ah, I'm stuck on a nail!
04:14Ha ha ha!
04:16Oh god, that's painful!
04:17Number 16. Artie Ziff
04:19Marge's marriage to Homer is a mixed bag, to say the least.
04:23But she could have done way worse.
04:25Artie Ziff was Marge's prom date.
04:27They were even crowned prom king and queen.
04:30But Artie has a dark side, as shown when he rips Marge's dress in his boundary-traversing lust.
04:35Oh really, I mean it! Now stop it!
04:39I'm sorry, Marge.
04:41Take me home, Artie!
04:42Years later, Artie is now the fifth richest man.
04:45He is still very much obsessed with Marge, even offering her a million dollars to spend a weekend with her.
04:52His forceful ways rear their ugly heads once more, though, and Marge refuses him again.
04:57Mmm! Get off me, you little nerd!
05:00Ah!
05:01As a seeming apology, he gives Homer a device to fix his snoring,
05:06which doubles as a secret camera, spying on Marge and giving her subliminal messages.
05:11What a delightfully written creep.
05:13Dump'em! I traveled the world in the seven seas.
05:18I am watching you through a camera!
05:21Number 15. Cecil Terwilliger
05:23Villainy sometimes runs in the family.
05:26That's the case at least with Sideshow Bob's whole family, including his cute son.
05:31But his brother is a good competitor for Bob's villainy.
05:33I can't imagine what you mean.
05:35After his release from prison, Sideshow Bob roams with his brother Cecil,
05:38also effete, eloquent, and with a tendency towards homicide.
05:43In fact, Cecil plans to frame Bob for the embezzlement of funds from Springfield's
05:47dam project, intentionally constructed with poor materials.
05:50But everyone will know you did this!
05:53Perhaps.
05:54Or perhaps they'll blame the master criminal.
05:57You know, the one who's been working at the dam and has a grudge against Springfield.
06:01It turns out Cecil resents Bob for upstaging him at auditions as Krusty the Clown's sidekick.
06:06When Cecil is arrested, so is Sideshow Bob.
06:09Kane has nothing on this brother.
06:12Tell them they'll live to regret this.
06:13You'll live to regret this!
06:16Number 14. Lucille Batsukowski
06:18There should be more love towards the classic Simpsons episodes.
06:22The show's greatness was apparent even in this season 1 finale,
06:25where Bart and Lisa get a babysitter from hell.
06:27You must be the babysitter!
06:29Yes, I am Ms. Bats.
06:31Well, just don't stand there, boy.
06:32Help Ms. Bats with her suitcases.
06:35I can handle my own luggage.
06:36The surly Ms. Bats turns out to be a wanted burglar.
06:39The babysitter bandit, in fact.
06:41Bats ties them up.
06:42But luckily, Maggie saves her siblings.
06:45Bart knocks her out with a baseball bat.
06:47But Ms. Bats escapes when Homer and Marge arrive home,
06:49mistakenly believing her to be a victim.
06:51Just so there's no hard feelings, here's double your pay.
06:54It's a shame she only appears in this one episode.
06:57Her villainy game was strong.
06:59Don't turn your back on that boy for a second.
07:02Ain't that the truth?
07:03Number 13. Jimbo, Dolph, and Kearney
07:05Who can forget this adolescent trio?
07:08While they don't get as much development or plot lines as main tormentor Nelson,
07:12these three get plenty of hilariously villainous moments.
07:15Most of their crimes involve juvenile delinquency,
07:18such as convincing Bart to cut off the head of Jebediah Springfield's statue in season 1.
07:22Wish someone really would cut his ugly old head off.
07:25You do?
07:26Yeah, that'd be cool.
07:27Sure would cheese everybody off.
07:29The years, though, have shown a softer side to these three.
07:33Dolph is an accomplished polyglot,
07:35Jimbo is the mastermind with a bad home life,
07:37and Kearney is an ex-convict and the father of a teenager.
07:41And of course, their parents are of the same bad strain.
07:44The thing is, Bart really loves that belt and...
07:47Hey, something's wrong with this guy.
07:50Number 12. Malloy
07:52This cat is one hell of a burglar.
07:54He's introduced in this season 5 episode,
07:57stealing Lisa's saxophone,
07:58Bart's stamp collection,
07:59and Marge's necklace in one fell swoop.
08:02He even stole Flanders' shroud of Turin beach towels.
08:05You folks got robbed too.
08:06The burglar took my shroud of Turin beach towels.
08:09When Malloy finally gets arrested after stealing the world's biggest zirconia,
08:13he sends the townspeople on a wild goose chase towards a hidden treasure.
08:16Hi.
08:18You take highway 201 south for 15 minutes.
08:22You take a left, a left.
08:26The treasure was just a piece of paper,
08:28explaining the plot so that Malloy could escape jail unseen.
08:32Malloy is definitely one of the most clever of the show's minor villains.
08:36I have already used this time to escape from your jail.
08:39Bondus wishes.
08:40We can't make out the signature.
08:42Keep digging.
08:43We're bound to find something.
08:45Number 11. Russ Cargill
08:46Did you know that The Simpsons writers had considered making Hank Scorpio the villain for the 2007 movie?
08:52Great as Scorpio is,
08:53we're glad this brand new villain was created.
08:56When Springfield is faced with a pollution crisis,
08:59Cargill comes in as head of the EPA to make it worse.
09:02My name is Russ Cargill and I am head of the EPA.
09:06The what?
09:07Environmental Protection Agency.
09:09Come again?
09:10Look, I'm a man on a big TV.
09:11Just listen.
09:12One option he presents to President Arnold Schwarzenegger is to seal the city in a glass dome.
09:17To prevent your poisons from spreading,
09:19your government has sealed you all within this dome.
09:21Believe me, it's the last thing we wanted to do.
09:25I do own the company that makes the dome, but that's beside the point.
09:28Furious at the residents' attempts to destroy the dome,
09:30Cargill tricks the president to order the town's destruction.
09:33And as a linchpin to his villainy,
09:35Cargill also tries to kill Homer and Bart.
09:38Now this is a villain indeed.
09:40Well, always leave them laughing.
09:43Goodbye, sir.
09:51Number 10. Snake.
09:53Springfield has many colorful criminals,
09:55but one of its most recurring lawbreakers is Snake,
09:58whose last name is variously stated to be Turley or Jailbird.
10:02One, two, three, four, five, six, seven, eight, ten.
10:06Bye!
10:07The latter is quite apt,
10:09as he's generally in and out of prison.
10:11Though, given the ineptitude of Springfield's finest,
10:14that's hardly surprising.
10:15An interesting twist on the career criminal archetype,
10:18Snake brings a lot of hilarity to otherwise tense situations,
10:21given his changeable attitude and surfer dude accent.
10:24Oh, goodbye student loan payments.
10:27Fond of fast cars and notoriously intolerant of singing and music that isn't rock and roll,
10:33Snake is one premium villain, dude.
10:35Hey, that smells like regular.
10:38She needs premium, dude.
10:40Premium!
10:42Number 9. Frank Grimes.
10:44An unlucky, hard-working co-worker of Homer's at the nuclear plant,
10:48Frank Grimes only appears in one episode,
10:50but he makes a big and dark impression.
10:53Don't you realize how close he just came to killing yourself?
10:56Grimes gets to know Homer and is continually astonished
10:59that such a lazy, fat moron is able to get so far in life by accident,
11:03when all his efforts have seemingly been for naught.
11:06Hi, Grimey old buddy.
11:08I'm not your buddy, Simpson.
11:09I don't like you.
11:10In fact, I hate you.
11:11Stay the hell away from me,
11:13because from now on,
11:14we're enemies.
11:15Declaring himself Homer's enemy,
11:17Grimes attempts to sabotage Homer,
11:19eventually leading the entitled man to become unhinged
11:22and to imitate Homer's idiocy by touching electrical wires,
11:26which kills him.
11:27I don't need safety gloves,
11:29because I'm Homer Simpson.
11:31Grimes' son even appears to carry on his father's grudge
11:34against the dopey Simpson patriarch.
11:37Frank Grimes, Jr.
11:39Frank Grimes.
11:42Don't you remember?
11:44Your ape-like incompetence drove my father insane.
11:47Number 8.
11:48Nelson Muntz.
11:50As Springfield Elementary School's foremost meanie,
11:52Nelson Muntz is the quintessential childhood tormentor.
11:55Frequently beating up his classmates,
11:58including Bart,
11:59Milhouse,
12:00Martin,
12:00and even Lisa on occasion,
12:02Nelson never fails to mock someone when they're down,
12:05usually with his signature laugh.
12:08Though generally dimwitted and brutish,
12:10Nelson is driven to lash out at others by his own insecurities,
12:13and is sometimes shown to have a sensitive side.
12:23While he is threatening to other kids,
12:25adults can often knock him down to size
12:27and put him in his place.
12:29Hey, everybody, look at this.
12:32It's that boy who laughs at everyone.
12:35Let's laugh at him.
12:38Number 7.
12:39Hank Scorpio.
12:41The personable CEO of Globex Corporation,
12:43Hank Scorpio hires Homer to work for him
12:46in an idyllic planned community.
12:48I'm Hank Scorpio.
12:48Wow, my boss.
12:50Don't call me that word.
12:51I don't like things that elevate me above the other people.
12:54Fast talking and given to tangents,
12:56Scorpio is an ideal boss
12:58who motivates Homer to actually be good at his job.
13:01It's just one problem.
13:02He is a supervillain.
13:04This is Scorpio.
13:05I have the doomsday device.
13:07You have 72 hours to deliver the gold,
13:09or you face the consequences.
13:11Bent on conquering the world with doomsday devices,
13:14and facing off against Bond-style secret agents,
13:16Scorpio is completely evil to the outside world,
13:19even if he's nicer to his employees than most legitimate bosses.
13:22Though he only appears prominently in one episode,
13:25every scene he's in is incredibly entertaining.
13:29And he's got a catchy theme song, too.
13:31Scorpio!
13:33He'll sting you with his dreams of power and wealth.
13:37Beware of Scorpio!
13:39Number 6, Jessica Lovejoy.
13:42As the Reverend's daughter,
13:43Jessica Lovejoy shows a goody-two-shoes attitude to adults,
13:46but she's actually a huge troublemaker,
13:49which is what attracts Bart to her and she to him.
13:52Wow, there is a God.
13:55However,
13:55Bart eventually realizes that she has a lust for crime and danger
13:59that outstrips even his own.
14:02Teamwork! Come on, Bart!
14:04Her willingness to get him into trouble
14:06when he tries to distance himself from her
14:08leads her to become a formidable young femme fatale for him and Lisa.
14:12Her duplicitous nature and excellent acting skills
14:14should be no surprise either,
14:16given that she's voiced by regular Oscar winner Meryl Streep.
14:19Remember, I'm the sweet, perfect minister's daughter.
14:23And you're just yellow trash.
14:25Huh?
14:26Number 5, Kang and Kodos.
14:28A staple of the Simpsons' Treehouse of Horror episodes,
14:31Kang and Kodos are a duo of terrifying,
14:33tentacled, cycloptic aliens
14:35that may or may not be siblings.
14:37Foolish humans.
14:38Oh yes, Kodos.
14:40Earth is now ripe for the plot.
14:42Most of the time,
14:44they're shown to have malevolent intentions
14:45for the Simpson family and other Earthlings,
14:47often taking over Earth.
14:49Either by hook or by crook.
14:51Like the anthology episodes they appear in, though,
14:54they're not always portrayed consistently,
14:56with their first appearance
14:57actually revealing them to be benevolent.
14:59Kodos and I are taking you to Rigel 4,
15:02a world of infinite delights
15:03to tantalize your senses
15:05and challenge your intellectual limitations.
15:08Even so,
15:09their drooling manic grins and booming voices
15:12make some of the lines they deliver
15:14quite frightening and funny.
15:16Well, I believe I'll vote for a third party candidate.
15:18Go ahead.
15:19Throw your vote away.
15:25Number 4.
15:26Lyle Landley.
15:28When the town holds a meeting
15:29to decide what to do with money
15:30they won from a fine,
15:32they are approached by Lyle Landley,
15:34who quickly sells them on building a monorail
15:36with the aid of an incredibly catchy song.
15:47However, Marge and Lisa suspect that Lanley may be pulling one over on Springfield,
15:51and an investigation into his previous monorail endeavors
15:54reveals that he's a con artist in the vein of the musical The Music Man.
16:03Played to exuberant perfection by the late great Phil Hartman,
16:06Lyle Lanley is a slick and slimy villain we were all glad to see get his Just Desserts.
16:12Oh no!
16:13There he is!
16:14Z3F!
16:20Number 3, Fat Tony.
16:21Sorry we're late, could we have the money now?
16:25Springfield's resident mob boss, Fat Tony D'Amico is one of the biggest criminals in town,
16:30frequently performing scams, extortion and whackings that almost always see him come out on top.
16:35Few targets are off limits, and he even once extorted an elementary school.
16:44Given how ruthless and threatening he can be, the moments when Fat Tony does say funny things
16:49are just that much funnier, since they clash with his tough guy image.
16:52Garfield or Lovis?
16:54I prefer the cat, he hates Mondays, we can all relate.
16:59While glimpses of a softer nature are there, he still remains one of The Simpsons most intimidating villains.
17:06This is a pretzel town, pretty boy.
17:08Number 2, Sideshow Bob.
17:10Bart might suffer through Nelson, but his arch nemesis is undoubtedly Robert Terwilliger Jr., better known as Sideshow Bob.
17:18A self-proclaimed genius with a perpetual vendetta against the Simpson boy,
17:26Bob is legitimately menacing, and acts like a cross between Hannibal Lecter and Wile E. Coyote.
17:31Always brilliant, but never able, or sometimes even wanting, to achieve his goal to kill Bart.
17:37Played spectacularly by Kelsey Grammer, Bob is sometimes rivaled by his brother Cecil,
17:45but Bob comes out on top for us.
17:47You want the truth?
17:49You can't handle the truth!
17:51No truth handler, you!
17:53Overall, Sideshow Bob is not just a great Simpsons villain.
17:57He's a great villain, period.
17:59Sometimes I wish this damn would burst, and bury this cursed town.
18:05Before we continue, be sure to subscribe to our channel,
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18:19Number 1. Mr. Burns
18:23Charles Montgomery Burns is the richest man in town, and indisputably, it's most hated.
18:29He's also Homer's boss.
18:30My name is Homer J. Zip.
18:32Ow!
18:33Son.
18:34Mm. Sounded large when I ordered it.
18:36Selfish, cruel, and money-grubbing, Mr. Burns has little sympathy for anyone,
18:41and frequently endangers his employees, strangers, and often the entire town with his hateful winds.
18:47Whether he's releasing his hounds on visitors to his home, or declining to donate money to charity,
18:54Mr. Burns oozes hateful capitalistic greed.
18:57I call it the Burns Omni-Net.
19:00It sweeps the sea clean.
19:02Even so, his antiquated views, forgetfulness, and daffy attitude can make him somewhat endearing.
19:08All in all, he's an excellent villain, and arguably the best one on the show.
19:13Are you saying boo or boo-erns?
19:16Boo!
19:18I was saying boo-erns.
19:21Which other villain from The Simpsons was excellent, or simply deserves more love?
19:25Let us know in the comments down below.
19:27A slick Hollywood picture to gloss over my evil rise to power like Bugsy or Working Girl.
19:33Working Girl.
19:34Two-
19:37Two-
19:38Three-
19:54One-
19:55Two-
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