The Simpsons: 5 Best (& 5 Worst) Villains

Over the course of thirty-one years, The Simpsons has had to introduce its fair share of bad guys. Whether they’re present at all times, seemingly lacking the ability to age and appear multiple times throughout the show, or they’re a nice little one-off, there have certainly been a few.

We’ve ranked the five best and five worst bad guys ever to antagonize the Simpson family, based on how much we like them being on our screens—not by how quote-unquote “bad” they actually are.

10 Best: Nelson Muntz

Nelson might well be the deepest of all of the bad guys from across the history of The Simpsons. He certainly gets the most character development: from loving Lisa to revealing his traumatic past to being the man to replace “smell ya later” with goodbye.

He does lack a certain level of consistency, occasionally being given entire episodes where a deep emotionality is revealed, and then being on hand to deliver one emotionless ‘haw-haw’ in the very next episode. However, he is probably the most iconic animated bully of all time.

9 Worst: Frank Grimes

Grimey is Homer’s arch-nemesis. Whether or not he appears as the primary antagonist of one of the best ever episodes of The Simpsons or not, he is quite annoying, isn’t he? Constantly whining and thinking he is second-best to someone else is something everyone has to deal with. Homer gets lucky and manages to live a great life despite his incompetence, but it is Frank Grimes’ jealousy that ends up literally killing him. It’s a sad story at its heart, but his personality makes it a lot easier to get over.

8 BestT: Hank Scorpio

Plucked right out of the greatest episode of the show ever, Hank Scorpio is one of those exceptional one-off villains. He starts off as what might be the loveliest man ever before it is revealed that he is some sort of global supervillain about to kill James Bond…

It’s almost difficult to describe him as a villain when he gives Homer the Denver Broncos football team as a gift, but it’s pretty much impossible to deny when he asks him to kill a few people on his way out.

7 Worst: Snake Jailbird

Snake is a great character who is brilliantly funny, but he gets old. There are a few characters in The Simpsons who have one line of personality—e.g. Ralph’s stupidity or Comic Book Guy’s obsession with comic books—but never get old. Unfortunately, Snake’s voice and 90s attitude just don’t have the same longevity. He’s basically an old version of Bart, and we all know that he got boring by season two.

6 Best: Monty Burns

Possibly challenging Nelson Muntz for the most iconic Simpsons bad guy throne is Mr. Burns. The incredibly old, incredibly wealthy, incredibly evil owner of the Nuclear Power Planet has tried to block out the sun, turned a recycling plant on its head, and turned Santa’s Little Helper into a vicious hound.

His sinister voice and subservient man servant Smithers combine like meat and gravy, and every episode in which he stars is bound to be a winner.

5 Worst: Artie Ziff

He might win the award for having one of the funniest voices in the show, but Artie Ziff doesn’t take how prizes for originality. Remember that one episode where Monty Burns fell in love with Marge? Well, that’s all Artie is, just with a new backstory. The two dated a long time ago, and, while she went on to live a happy life with Homer, he lived a successful life that has made him millions, all the while still pining after Marge. His storylines are all the same, and his character doesn’t age very well.

4 Best: Fat Tony

The most stereotypical mob boss in the history of television is also one of the greatest bad guys in The Simpsons. While most of the characters introduced seem to have a specific vendetta against someone for some reason, Fat Tony and his crew aren’t discriminatory in the slightest. He’ll just as happily team up with Mayor Quimby for some off the books crime as he would attempt to kill him at a Gala that Mark Hamill happens to be attending.

3 Worst: Russ Cargill

On his own, Russ Cargill is a fine character. He’s funny, full of quips, and he’s voiced by the inimitable Albert Brooks. His only appearance is in The Simpsons Movie, where he plays the head of the EPA as they hunt down the Simpson family.

The problem with Russ Cargill is that he is just Hank Scorpio. In fact, he is literally voiced by the same actor. In fact, the primary antagonist of The Simpsons Movie was supposed to be Hank Scorpio. Having this knowledge and finding out that they changed their plans only to make basically the exact same character but a little bit worse is just frustrating.

2 Best: Sideshow Bob

It’s hard to suggest that anyone other than Sideshow Bob is the best villain in The Simpsons. Everything about him is just perfect, from the skillful voice acting of Frasier himself, Kelsey Grammer, to the sinister evil in his voice at every turn. There also seems to be a bit of a pattern emerging with the character where almost every episode he appears him goes down in history as one of the greatest the show has ever produced. He is simply unbeatable.

1 Worst: Baby Gerald

It might seem pointless to put Baby Gerald on this list given that his appearances are very rare and he literally is incapable of speech, but his existence is pointless. The main reason he is there is to give Maggie an angry side, to show us that she can move away from being the sweet innocent baby we all know and love.

The problem is, we don’t need these Family Guy-style sideline stories in which Maggie and Gerald engage in silent warfare. We don’t need to see Maggie’s brow furrow in hatred. He just doesn’t need to exist.