The Simpsons' 10 Best Villain Characters

The Simpsons boast some very impressive villains over the years, with the best ones juggling the show's sense of comedy with genuine thrills and threats. The Simpsons always works best when it's somewhere between grounded family dramedy and absurd silliness, which is reflected in the show's main characters. That extends 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 characters can easily slot into brief villain roles like Agnes Skinner, Snake Jailbird, and Luann Van Houten, but the show has always afforded them some extra depth to keep them more complex and adaptable. However, some characters in The Simpsons have been established primarily as antagonists, actively endangering the world and threatening the Simpsons in their plans. Some have only made one appearance, while others have been constants of the show since the earliest seasons. Here are the best ten villains from across thirty-six seasons of The Simpsons

10 Lyle Lanley

Played By Phil Hartman

Lyle Lanley is one of The Simpsons' most memorable villains, and a good showcase of how the show can balance dangerous character beats with the inherent silliness of the series 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 investing millions into his barebones monorail system, Lyle embodies the smarmy traits that define Hartman's other characters like Lionel Hutz and Troy McClure but with a decidedly darker edge.

A clear parody of Harold Hill from The Music Man, Lyle's smooth-talking allows him to trick even typically intelligent characters like Lisa, allowing him to escape the town while leaving the townsfolk to fend for themselves. Lyle is a consistently funny character in the episode thanks to the sheer lack of effort he puts into his cons, all bolstered by a bombastic sense of charm. Lyle's single appearance remains one of The Simpsons' most memorable one-off characters and a great villain for the cartoon.

9 Russ Cargill

Played By Albert Brooks

Russ Cargill is the main antagonist of The Simpsons Movie, and Albert Brooks brings a larger-than-life element to the character to match that distinction. The head of the EPA, Cargill is revealed to be a ruthless and vindictive figure who seeks to eliminate Springfield and replace it with a new tourist attraction. Cargill is a very silly character, with a motor-mouth approach to villainy that sees him openly admit he's gone mad with power. None of that detracts from his surprisingly cold approaches to claiming power.

Cargill arranges for the President to condemn Springfield, and casually prepares to shoot Homer in the face with a shotgun when his plan is thwarted. There's a bluntness to Russ Cargill that plays into the comedy of the situation, but that also amplifies the character's effectiveness as a villain. Coupled with enough social power to put all of Springfield at risk, Cargill was an ideal villain for the film's expanded narrative.

8 Artie Ziff

Played By Jon Lovitz

Introduced in season 2's "The Way We Was," Artie Ziff has become a semi-recurring presence in The Simpsons. Introduced as another suitor looking to impress Marge while she and Homer were in high school, Artie is presented as everything Homer isn't. While this initially means well-educated and soft-spoken, he also proves to be a far more selfish and aggressive character than Homer has ever been with Marge, even groping her following their prom date. Artie has subsequently reappeared as a weasley but wealthy rival for Marge's affections.

Although he's never truly succeeded in these efforts, his attempts (and the drama it has induced on their relationship) has helped cement Artie as one of Homer's more pronounced rivals in The Simpsons. Even his most recent appearance in season 31's "Hail to the Teeth" highlighted his creepy and possessive attitude towards Marge, building scores of androids resembling her to try and win her back. More pathetic than threatening, Artie has nevertheless become a surprisingly consistent threat to Homer and Marge's relationship.

7 Cecil Terwilliger

Played By David Hyde Pierce

Sideshow Bob's brother, Cecil Terwilliger debuted in season 8's "Brother From Another Series." Initially portrayed as a more innocent answer to his homicidal brother, Cecil's debut episode established him as a more overtly murderous and brutal character. Cecil's more grounded approach to evil came close to killing Bart and Bob, with the character even dispensing with Bob's typically theatrical approach to murder and simply throwing Bart off the side of a dam.

Cecil even managed to inflict massive damage on Springfield thanks to destroying the town's dam, giving him an edge over Bob's failed attempts to bring down the city. Cecil only suffers from a lack of appearances, as he's only had one other prominent appearance since his debut episode. However, Cecil remains a deeply memorable villain for his ruthless approach to crime and his upper-crust comedy serving as a fun direct mirror to Sideshow Bob.

6 Frank Grimes

Played By Hank Azaria

Introduced in season 8's "Homer's Enemy," Frank Grimes is one of the darkest characters in the history of The Simpsons. Established as a grounded and stern man looking to move forward in his life thanks to a new position at the Nuclear Power Plant, Grimes quickly decides that the lazy and perceptually relaxed Homer is his greatest enemy. Grimes draws attention to Homer's failings but also serves as an ideal contrast to him.

This highlights how Homer also meets a bittersweet and often difficult life but with a sense of love and joy that Grimes can't match. Grimes is a perfect contrast to Homer, the anthesis of Homer and underscores the importance of the show's embrace of silly joy and earnest sweetness in contrast to self-aware and harsh reality. Grimes' death may have been unexpectedly dark and quietly tragic, but it also underlined a very important element of the show's ethos and Homer's character as a whole.

5 Kostas Becker

Played By Brian Cox

The central villain to the season 33 two-parter "A Serious Flanders," Kostas Becker stands out from other villains in The Simpsons because of how dark he is. Becker is a criminal debt collector who discovers that a small fortune he lost decades ago has resurfaced in Springfield. Played by Brian Cox with a steely cold exterior and a monstrous core, Becker slaughters his way through Springfield in pursuit of his riches.

Unlike most other villains, the non-canon status 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 allies. Becker's serious demeanor purposefully bristles against the sillier elements of The Simpsons, while also serving as a pitch-perfect parody of the ruthless killers who appear in shows like Breaking Bad and Justified. Kostas wouldn't fit in the show naturally but makes for an ideal threatening villain in an experimental approach to The Simpsons.

4 Hank Scorpio

Played By Albert Brooks

Hank Scorpio is a frequent fan favorite and one of The Simpsons' best-ever one-off characters. Initially presented as a genial and open-hearted new boss for Homer in season 8's "You Only Move Twice," Scropio is steadily revealed to be a James Bond-style villain who seeks to take over the world. Neither side detracts from the other, however, which is a testament to the episode's strong writing and Albert Brooks' wonderful performance. He's a sweet-natured man who slaughters countless people, a contradiction that the show plays for big laughs.

Brooks brings an unexpected depth to super villain, especially during his final chat with Homer where he sadly agrees that Homer can't sacrifice his family for a dream job. The fact that they have a genuine and emotional conversation in the middle of a climactic battle scene taken straight from any number of James Bond films only adds to the absurdity that underscores the best episodes of The Simpsons. Hank Scorpio is a perfect one-and-done character, whose memorable appearance ranks among The Simpsons' very best.

3 Fat Tony

Played By Joe Mantegna

Introduced in season 3's "Bart the Murderer," Fat Tony has proven to be a surprisingly flexible character even while remaining one of Springfield's most dangerous. The local mob boss who runs much of the organized crime in Springfield, Fat Tony was defined early on as an over-the-top and self-aware parody of Italian Gangster stereotypes. Plenty of episodes have mined the character for unexpected laughs, teasing out a sensitive side while playing his overt crimes for big laughs.

However, Fat Tony also remains one of Springfield's only genuinely dangerous characters. He's repeatedly threatened multiple characters across the show's cast, with season 34's "The Many Saints of Springfield" pitting him against someone as effortlessly innocent as Ned Flanders. Fat Tony is one of the few characters in The Simpsons that the show can play for genuine intensity, although his sillier moments (and a typically impressive performance from Joe Mantegna) give him an adaptability perfectly suited for the series.

2 Mr. Burns

Played By Harry Shearer

Introduced in season 1 and consistently serving as The Simpsons' go-to villain, Mr. Burns has cemented himself over the past three and a half decades as one of modern pop culture's best antagonists. The cartoonishly wealthy business tycoon can only match his riches with his cruelty. The absurd comical nature of The Simpsons allows Mr. Burns to be typically utilized well as a silly villain, a character who can set a plot in motion while still being a natural source of comedy.

However, some episodes have highlighted how fearsome the character can be, with Mr. Burns' dramatic turns in episodes like season 7's "Raging Abe Simpson and His Grumbling Grandson in 'The Curse of the Flying Hellfish'" highlighting what makes him so memorably dangerous. Mr. Burns is one of the most adaptable villains in modern fiction, able to work on large-scale plots and personal stories alike. This adaptability fits in perfectly to The Simpsons' flexible universe and makes him an ideal central antagonist for the show.

1 Sideshow Bob

Played By Kelsey Grammer

One of The Simpsons' funniest characters and an ideal antagonist for the show, Sideshow Bob is the best villain in The Simpsons. Introduced in season 1's "Krusty Gets Busted," Sideshow Bob's initial gag of being an erudite and well-spoken criminal mastermind in the guise of a TV clown sidekick quickly gave way to an ideal villainous balancing act. Bob is effortlessly funny, with Kelsey Grammer's performance remaining remarkably consistent across several different schemes and tones.

The character's theatrical side and bombastic delivery is constantly undercut by some of the show's best physical comedy, such as the infamous rake gag. However, none of that removes the genuine peril he can bring to a situation. Episodes like season 5's "Cape Feare" play these horrific bits for comedy, but still find ways to make Bob quietly unnerving and threatening. The result is a perfect villain, someone who can played for laughs one minute and thrills the next. It's that adaptability but consistent characterization that elevates the best of The Simpsons, including Bob.

Source: Screen Rant