The Simpsons
The Simpsonsboast some very telling villains over the years , with the dependable 1 juggling the show ’s sense of funniness with unfeigned tingle and threat . The Simpsonsalways works best when it ’s somewhere between strand syndicate dramedy and preposterous fatuousness , which is reflected in the show ’s independent characters . That reach out to the characters who find themselves serving as antagonists , going up against the Simpsons in plenty of ways ( like Kang and Kodos , who are more often played for laughs in the"Treehouse of Horror " episodes ) .
Many character can easy slot into briefvillain roles like Agnes Skinner , Snake Jailbird , and Luann Van Houten , but the show has always afforded them some excess deepness to keep them more complex and adaptable . However , some characters inThe Simpsonshave been launch in the first place as antagonists , actively endangering the world and threatening the Simpsons in their program . Some have only made one appearing , while others have been constants of the show since the earliest season . Here are the best ten villains from across thirty - six seasons ofThe Simpsons
10Lyle Lanley
Played By Phil Hartman
Lyle Lanley is one ofThe Simpsons ' most memorable villains , and a good vitrine of how the show can balance unsafe character heartbeat with the inherent absurdity of the serial publication as a whole . Played by Phil Hartman , Lyle Lanley is the antagonist of season 4 ’s " Marge vs. the Monorail . " A slick singing conman who tricks Springfield into adorn 1000000 into his barebones monorail system , Lyle embody the smarmy trait that defineHartman ’s other character like Lionel Hutz and Troy McClure but with a decidedly darker edge .
Lyle is a consistently funny role in the episode thanks to the sheer lack of cause he puts into his flimflam , all bolstered by a orotund good sense of charm .
A open parody of Harold Hill fromThe Music Man , Lyle ’s smooth - talk allows him to trick even typically healthy characters like Lisa , allowing him to escape the town while leaving the townsfolk to resist for themselves . Lyle is a consistently funny character in the sequence thanks to the plain lack of drive he puts into his cons , all bolstered by a turgid sense of charm . Lyle ’s unmarried appearance stay one ofThe Simpsons ' most memorable one - off theatrical role and a enceinte villain for the cartoon .
9Russ Cargill
Played By Albert Brooks
Russ Cargill is the master antagonist ofThe Simpsons Movie , and Albert Brooks brings a declamatory - than - lifespan chemical element to the character to twin that distinction . The brain of the EPA , Cargill is break to be a remorseless and despiteful figure who seek to rid of Springfield and replace it with a new tourer attractiveness . Cargill is a very silly lineament , with a motor - oral cavity approach to villainy that picture him openly allow in he ’s gone brainsick with power . None of that detracts from his surprisingly dusty glide path to claim power .
Cargill arranges for the President to condemn Springfield , and nonchalantly devise to shoot Homer in the face with a scattergun when his plan is thwarted . There ’s a dullness to Russ Cargill that play into the funniness of the situation , but that also overdraw the character ’s effectiveness as a villain . Coupled with enough social power to put all of Springfield at peril , Cargill was an idealistic villain for the film ’s expanded narrative .
8Artie Ziff
Played By Jon Lovitz
usher in in season 2 ’s " The Way We Was , " Artie Ziff has become a semi - recurring presence inThe Mrs. Simpson . Introduced as another suitor expect to impress Marge while she and Homer were in eminent schoolhouse , Artie is presented as everything Homer is n’t . While this initially means well - develop and soft - spoken , he also proves to be a far more selfish and fast-growing character than Homer has ever been with Marge , even groping her following their prom appointment . Artie has subsequently reappear as a weasley but flush rival for Marge ’s affections .
Artie has nevertheless become a surprisingly consistent threat to Homer and Marge ’s kinship .
Although he ’s never in truth succeeded in these feat , his attempt ( and the dramatic event it has induced on their relationship ) hashelped cementArtie as one of Homer ’s more pronounced rivalsinThe Simpsons . Even his most late appearance in time of year 31 ’s " Hail to the Teeth " spotlight his creepy-crawly and genitive posture towards Marge , building scores of androids resembling her to seek and gain ground her back . More pathetic than threatening , Artie has nevertheless become a amazingly consistent terror to Homer and Marge ’s relationship .
7Cecil Terwilliger
Played By David Hyde Pierce
Sideshow Bob ’s chum , Cecil Terwilliger debut in time of year 8 ’s " Brother From Another Series . " Initially portray as a more free answer to his murderous brother , Cecil ’s entry episode give him as a more overtly murderous and brutal character . Cecil ’s more grounded approach shot to evil came nigh to killing Bart and Bob , with the charactereven dispensing with Bob ’s typically theatrical approach to murderand simply throwing Bart off the side of a dike .
Cecil reappear in season 19 ’s " Funeral For a Fiend , " alongside the rest of Sideshow Bob ’s household .
Cecil even managed to impose monumental damage on Springfield thanks to destroying the town ’s dam , give him an edge over Bob ’s failed attempt to bring down the city . Cecil only suffers from a lack of appearances , as he ’s only had one other big coming into court since his introduction sequence . However , Cecil remains a deeply memorable baddie for his ruthless access to crimeand his upper - crust comedy serving as a fun verbatim mirror to Sideshow Bob .
The Simpsons is a long-running animated TV series created by Matt Groening that satirically follows a working-class family in the misfit city of Springfield. Homer, a bit of a schmoe who works at a nuclear power plant, is the provider for his family, while his wife, Marge, tries to keep sanity and reason in the house to the best of her ability. Bart is a born troublemaker, and Lisa is his super-intelligent sister who finds herself surrounded by people who can’t understand her. Finally, Maggie is the mysterious baby who acts as a deus ex machina when the series calls for it. The show puts the family in several wild situations while constantly tackling socio-political and pop-culture topics set within their world, providing an often sharp critique of the subjects covered in each episode. This series first premiered in 1989 and has been a staple of Fox’s programming schedule ever since!
6Frank Grimes
Played By Hank Azaria
bring in in time of year 8 ’s " Homer ’s Enemy,“Frank Grimes is one of the obscure character in the story ofThe Simpsons . Established as a grounded and severe man looking to move onward in his life thanks to a new position at the Nuclear Power Plant , Grimes quick decides that the faineant and perceptually relaxed Homer is his nifty enemy . Grimes draws care to Homer ’s failings but also serves as an idealistic contrast to him .
An ex - showrunner on The Simpsons reveals that Nicolas Cage almost played Frank Grimes from the classic time of year 8 episode , " Homer ’s Enemy . "
This highlights how Homer also fulfil a bittersweet and often difficult life story but with a horse sense of making love and joy that Grimes ca n’t match . Grimes is a perfect contrast to Homer , the anthesis of Homer and underscores the grandness of the show ’s bosom of silly joy and earnest sweetness in contrast to ego - aware and harsh reality . Grimes ' death may have been unexpectedly dark and quietly tragic , but it also emphasize a very important ingredient of the show ’s ethos and Homer ’s character reference as a whole .
5Kostas Becker
Played By Brian Cox
The central villain to the season 33 two - parter " A Serious Flanders , " Kostas Becker stands out from other villains inThe Simpsonsbecause of how dark he is . Becker is a criminal debt accumulator who discovers that a minuscule fortune he lose decades ago has resurfaced in Springfield . playact by Brian Cox with a steely cold exterior and a monstrous substance , Becker massacre his way through Springfield in hobby of his riches .
Becker ’s serious demeanor purposefully bristles against the sillier elements ofThe Simpsons , while also serving as a pitch - perfect parody of the remorseless grampus who come out in shows likeBreaking BadandJustified .
Unlike most other villains , the non - canon condition of " A Serious Flanders " allows Becker to dispatch several longtime characters with brutal efficiency , especially during a shoot - out that kills Mr. Burns , Disco Stu , Fat Tony , and all his ally . Becker ’s serious behavior purposefully bristles against the sillier elements ofThe Simpsons , while also serve well as a pitch - perfect parody of the pitiless killers who appear in show likeBreaking BadandJustified . Kostas would n’t fit out in the show of course but form foran ideal threatening scoundrel in an experimental approach toThe Simpsons .
4Hank Scorpio
Hank Scorpio is a frequent fan favourite and one ofThe Simpson ' well - ever one - off characters . Initially presented as a affable and assailable - hearted new foreman for Homer in time of year 8 ’s " You Only Move double , " Scropio is steadily unveil to be a James Bond - mode villain who seeks to take over the mankind . Neither side detracts from the other , however , which is a testament to the episode ’s strong composition and Albert Brooks ' fantastic carrying out . He ’s a sweet - natured valet de chambre who slaughters countless people , a contradiction in terms that the show dally for magnanimous laughter .
As reported byScreen Rant , Hank Scorpio was considered as the master villain forThe Simpsons Moviebut was supercede with Russ Cargill .
Brooks bring in an unexpected deepness to top-notch scoundrel , especially during his final chat with Homer where he sadly jibe that Homer ca n’t give his family for a pipe dream job . The fact that they have a genuine and excited conversation in the midriff of a climactic battle scene taken direct from any number of James Bond films only sum up to the fatuousness that underscores the undecomposed episodes ofThe Simpsons . Hank Scorpio is a everlasting one - and - done lineament , whose memorable appearance ranks amongThe Simpsons ' very best .
3Fat Tony
Played By Joe Mantegna
Introduced in time of year 3 ’s " Bart the liquidator , " Fat Tony has proven to be a astonishingly elastic character even while remaining one of Springfield ’s most dangerous . The local crime syndicate boss who hightail it much of the mastermind crime in Springfield , Fat Tony was define early on as an over - the - top and ego - aware parody of Italian Gangster stereotype . raft of episodes have mine the character for unexpected laughs , teasing out a sensitive side while playing his open crimes for grown laughs .
Despite Fat Tony dying in time of year 22 of The Simpsons , season 33 managed to defeat off the eccentric again thanks to the show ’s loose approach shot to canon .
However , Fat Tony also remains one of Springfield ’s only authentically dangerous characters . He ’s repeatedly threatened multiple grapheme across the show ’s cast , with season 34 ’s " The Many Saints of Springfield " pitting him against someone as effortlessly innocuous as Ned Flanders . Fat Tony isone of the few type inThe Simpsonsthat the show can play for actual intensity , although his sillier moments ( and a typically telling performance from Joe Mantegna ) give him an adaptability perfectly suited for the series .
2Mr. Burns
Played By Harry Shearer
Introduced in season 1 and systematically help asThe Wallis Warfield Windsor ' go - to villain , Mr. Burns has cement himself over the past three and a half decades as one of forward-looking pop finish ’s best antagonists . The cartoonishly wealthy business big businessman can only match his riches with his cruelness . The ludicrous comic nature ofThe Simpsonsallows Mr. Burns to be typically utilized well as a silly villain , a character who can set a plot in movement while still being a natural reservoir of drollery .
However , some episodes have highlighted how horrific the case can be , with Mr. Burns ' dramatic bout in episode like season 7 ’s " Raging Abe Simpson and His Grumbling Grandson in ' The Curse of the Flying Hellfish ' " highlighting what makes him so unforgettably dangerous . Mr. Burns is one of the most adaptable villains in modern fabrication , able to work on great - graduated table plot of land and personal stories alike . This adaptability fits in dead toThe Simpsons ' pliable world and makes him an idealistic cardinal antagonist for the show .
1Sideshow Bob
Played By Kelsey Grammer
One ofThe Simpsons ' funniest characters and an ideal opposer for the show , Sideshow Bob is the best villain inThe Simpsons . Introduced in time of year 1 ’s " Krusty Gets bust , " Sideshow Bob ’s initial gag of being an erudite and well - spoken criminal mastermind in the pretense of a TV clown brother promptly gave way to an idealistic villainous reconciliation act . Bob is effortlessly funny , with Kelsey Grammer ’s carrying into action remaining outstandingly consistent across several different dodge and tones .
Notable Sideshow Bob Episodes OfThe Simpsons
Season
" Krusty Gets bust "
1
" Black Widower "
3
" Cape Feare "
5
" Sideshow Bob Roberts "
6
" Sideshow Bob ’s Last Gleaming "
7
" buddy From Another Series "
8
" Day of the Jackanapes "
12
" The Great Louse Detective "
14
" The Italian Bob "
17
" Funeral For A Fiend "
19
" The Bob Next Door "
21
" The military personnel Who Grew Too Much "
25
" Gone Boy "
29
" Bobby It ’s Cold Outside "
31
The eccentric ’s theatrical side and bombastic delivery is invariably undercut by some of the show ’s good strong-arm comedy , such asthe infamous rake gag . However , none of that removes the unfeigned endangerment he can bring to a post . Episodes like season 5 ’s " Cape Feare " play these horrific bits for comedy , but still find ways to make Bob quietly formidable and menacing . The result is a gross villain , someone who can play for gag one second and thrills the next . It ’s that adaptability but ordered characterization that elevates the best ofThe Simpsons , let in Bob .
generator : Screen Rant
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The Simpsons is a long - run animated TV series create by Matt Groening that satirically follow a working - category category in the misfit metropolis of Springfield . Homer , a second of a schmoe who works at a nuclear power works , is the provider for his family , while his wife , Marge , tries to keep sanity and reason in the house to the best of her ability . Bart is a bear troublemaker , and Lisa is his super - intelligent sister who find herself surrounded by masses who ca n’t understand her . lastly , Maggie is the mysterious baby who playact as a deus ex machina when the series calls for it . The show puts the family in several wild situations while constantly harness socio - political and pop - culture subject limit within their world , providing an often keen critique of the subject cover in each installment . This series first premiere in 1989 and has been a raw material of Fox ’s programming schedule ever since !
