While Springfield may not be
the most moral place around, its residents still tend to land
either on the good or grey side of the morality scale. Even troublemakers like Bart and
Homer can still be decent people. However, there are still those residents who fit more
on the dark side. But which of these characters only act bad, which of them are truly
bad, and which are just plain evil? I’m Kyle with WickedBinge, and this
is Simpsons Villains: Bad to Evil. We’re going to be starting off
this list with the least bad and working our way up to the
cruelest of the cruel. And, since we’re starting with the more
minor threats, we have no choice but to put Nelson Muntz as our least evil. Nelson has
certainly had an interesting arc over the course of this 30+ season series. Some
may even argue that he isn’t even a Bad character, fitting more on morally grey these
days. Still, he was certainly considered a villain all the way back in Season 1’s “Bart
the General”, where he beat Bart to a pulp for several days straight, bringing the poor
kid to tears at one point. From there, Nelsonmostly did typical bully things. From
cheating in the soapbox derby race, to threatening Bart and Milhouse, to stealing from several
students and even Superintendent Chalmers himself. He can be a pretty bad influence
on people like Bart, and even when Lisa believed that he could be good, he was willing
to betray her to both save face in front of his gang and to get back at Principal Skinner.
Though there were certainly other bullies at Springfield Elementary, none of them really
held the presence that Nelson did in those early years, given that he was often the
leader of the group. However, as the show’s gone on, he’s softened up significantly.
We’ve seen him form friendships with Bart and Lisa, as well as several moments where he’s
been on the side of good, such as when he tried to figure out the circumstances behind
Martin’s death in “Dial N for Nerder” or when he helped Lisa get back at Sherri and
Terri in “Sleeping with the Enemy”. Though he can still be aggressive and act like a bully
in later seasons, you easily get the sense that it’s more out of frustration and a lack
of positive influences than anything else. Next, we have Marge’s sisters, Patty and Selma.
Like Nelson, they aren’t particularly evil persay, but they can certainly be antagonists.
It’s no secret that they hate Homer as much as Homer hates them, and whenever
it seems like Homer is about to die, they revel in it and offer no real comfort to
Marge. They also tend to try and manipulate Marge into leaving Homer whenever it
seems like they’re about to break up. When they’re not trying to put a wedge between
them, they’re often just being antagonistic to Homer in general. In the episode “Homer
VS Patty and Selma”, they let Homer borrow money from them, and taunt him with it
throughout the episode, despite Homer already feeling plenty of shame about it. As for
Marge, even as kids the three of them weren’t too close, and as older sisters they would
often try and mess with Marge, discourage her or force her into doing their chores.
Probably the most villainous they’ve ever been is in the episode “Wedding for Disaster”, where
they straight up kidnap Homer just so he doesn’t re-marry Marge. So yeah, these are
some pretty awful sisters. However, their awfulness really only extends to Homer
and occasionally Marge. They clearly care about each other, and are decent aunts to
the Simpson kids with Selma being a pretty alright mother to her daughter, Ling. Selma
was also the one to tell Marge where Homer was in the flashback episode “I Married
Marge”. Not the worst relatives a family could have, but there’s definitely a reason no
one really likes visiting with these two. Up next is Waylon Smithers. Now, as Mr.
Burns’ right-hand man, you would think that this guy would be a lot higher up. But while
there’s no real excuse for simply “following orders”, when Smithers isn’t being ordered
by Burns, his own actions really aren’t that evil. Though he can be a jerk when he
wants, like when he grumbles at employees or when he tries to get Homer fired after
being jealous of his success in “Simpson and Delilah”, he’s mostly a reasonable guy.
He’ll sometimes get a temper when pushed tohis limits of anger and jealousy, and even
fought Homer at one point, but even this you can somewhat forgive since you can understand
his frustration. What really sets him apart from his boss/crush is that Smithers
has lines he won’t cross. He protects Homer in “Blood Feud” when he doesn’t want to
see him get beaten up, and he stands up to Burns when Burns tries to block out the
sun. The fact that he has a bit of morality already makes him less evil than Burns.
Still, when he IS willing to follow his boss, Smithers is able to do some pretty awful
things. From assisting with puppy kidnapping, to actually kidnapping Tom Jones, to
helping Burns cheat in the big Nuclear Plant softball game. On his own, he’s a nice enough
guy. But when you bring in all that he’s done and is willing to do for Mr. Burns,
you kinda have to consider him a villain on some
level. Next, we have Dwight Diddlehopper and
Jack Crowley, two one-time characters who have similar enough morality levels.
Coincidentally, they both also have a relationship with Marge. Dwight was a small-time bank
robber while Jack was an artist that was serving time. When Marge first meets
Dwight, she manages to convince him to give himself up and promises that she’ll visit him
in prison. When Marge breaks this promise, Dwight escapes and kidnaps her, taking
her to the amusement park where his mother abandoned him and wanting to spend time
with a motherly figure like Marge. As for Jack, he was also a small-time crook and
had been arrested for shooting Apu. After Marge saw his amazing art, she tried to get
him on a better path and even got him a job painting a mural for Springfield Elementary
- though this would end up backfiring majorly. While neither Dwight or Jack
are evil, they certainly have made some questionable decisions. Dwight was willing
to injure himself to save the day, buuut then tried to convince Marge to help him escape
jail again after he was healed. He’s also fairly mentally unstable in general. Jack
meanwhile let his anger get the better of him when he decided to torch not only the mural
but also Skinner’s car, and he even tried to lie to Marge about it. While Marge certainly
tried to help these guys get back on the side of good, it unfortunately just didn’t work out.
Speaking of Marge, next we have Artie Ziff, Marge’s ex. From the first time they met,
Artie and Homer were romantic rivals, with Artie seeing Homer as an oaf and Homer
seeing Artie as a snob and a jerk. While Artie was sweet towards Marge, he was also
more than a little pushy with her on their prom night. Okay so, this all seems like
small-time high school drama so far, so what puts him above crooks and an evil
businessman’s assistant? Well, as pushy as Artie could be, he could also be creepy and
manipulative, not to mention pretty obsessed with his one-time date. When he was rich,
he tried to use his wealth and influence to trick Marge into falling for him, even
recreating their prom night and trying to force her to kiss him. Then, in “The Ziff
WhoCame to Dinner”, Artie ends up pinning all of his debt onto Homer and getting him
arrested. Considering how nice Homer was to Artie in that episode, even after all their
history together, that’s pretty low. What keeps him from being put any higher is that, as
narcissistic and awful as Artie can be, he still tends to make the right choice and try to
make up for his actions when he sees how much they hurt Marge. He’s also never tried
to actually kill Homer, and as much of a low bar that is, we still give him credit for not
falling into THAT particular jealous ex trope. Snake Jailbird is probably Springfield’s
most famous - and infamous - crook. He’s constantly escaping jail and committing crimes,
usually at places like the Kwik-e-Mart or Moe’s Tavern. He’s even attacked the Simpsons
a couple times, albeit non-canonically, like in a Treehouse of Horror segment “Hell
Toupee” and in the second Simpsons clip show. While he mostly just robs businesses
and homes, he’s also stolen cars, cows, and - on one occasion - Mr. Burns’ girlfriend,
Gloria. He even tried to run down Bart in the season 3 episode “Separate Vocations”, so
while he doesn’t do it often, he’s not above hurting a child in his worst moments.
Thankfully, Snake is more interested in robbing people than killing them, which
keeps him from being put any higher. Another famous Springfield robber is Ms.
Botz, AKA the Babysitter Bandit. Though she’s only had one appearance, it was definitely
a memorable one - and not just because of that one animation clip you keep seeing
on your Twitter timeline. As part of a babysitting service, Ms. Botz has made it a
habit of tying up the kids she’s supposed to be babysitting and robbing their homes,
escaping before the parents get home and changing her identity to avoid getting
caught. The fact that she’s been able to successfully do this several times is both
impressive and kind of scary. If there’s any bright side to her crimes, it’s that Ms. Botz
never actually injures her victims - though she does threaten to. Honestly though, you
have to be a pretty despicable person to be willing to rob a family’s
home right in front of them. Moving away from the thieves to the more
threatening characters, we have Herman Hermann. Known for being more than a little
shady, Herman is a minor character that walks that line between being weird and
being an actual criminal. For the most part, Herman focuses on running his antique shop
where he sells ordinary items claiming they’re historical. This
isn’t that big of a crime, but it’s still shady - and it only gets worse from there. When Bart is trying to fight
back against Nelson, Grandpa recruits Herman into helping them. Although it’s just a water
balloon fight, Herman takes it with all the seriousness of an actual war, showing just
how unstable he can be. Though he doesn’t get too many instances to shine as a villain,
we see that he’s willing to kidnap, threaten people and hold them hostage in “22
Short Films about Springfield”. Given that thisscene is a homage to the film Pulp
Fiction, you know that whatever Herman was planning, it wasn’t going to be good. Herman
also ran a counterfeit jeans operation out of Homer’s garage in “The Springfield
Connection”. When Marge busted him, Herman took Homer hostage and actually tried to
kill Marge. This character is probably one of the darkest ones in the show, with his schemes
feeling a bit more serious than Snake’s. Maybe that’s why the writers tend to
keep him as a background character. Next is Frank Grimes Jr. Now, we’re sure
fans of Grimey are a bit miffed that we’re putting his son on the list instead of Grimes
himself. While we acknowledge that Grimey was indeed a jerk, and him trying to
humiliate Homer when he reached his limit was definitely a bad move, Grimey really only
caused harm to himself. His son, however, decided to take his anger towards Homer one
step further and actually tried to murder him. He first tried to kill Homer by locking
him in an overheating sauna. He then just tries shooting Homer, first at Moe’s Bar,
then at a Mardi Gras parade after cutting the breakline on his float. When he’s finally caught,
Junior explains that he only tried to kill Homer because Homer, in a sense, killed
Grimey by accidentally driving him insane. Though we can certainly understand Junior’s
side and can even feel sympathy for him, we can’t exactly excuse several murder attempts. Up next is Jack Lassen. Jack was another
one-time character, acting as Bart’s temporary teacher in season 26’s “Blazed
and Confused”. Instead of acting as a mature role model for his students, Jack is a bully
and focuses on tormenting Bart the most. He sees his bullying as a means of discipline,
and focuses on humiliating students like Bart and Nelson instead of actually trying to teach
them how to be better people. Later on in the episode, when Bart and Milhouse ruin
the Blazing Guy festival effigy that he was trying to light, Jack tries to torch Bart
and Milhouse instead as a means of revenge. Though certainly not the only villain on this
list who’s tried to kill a kid character, he’s the only one we see trying to light his young victim
on fire. After he’s fired from Springfield Elementary, Jack gets a new job as a prison
warden, a job he says will reward him for his quote “sociopathic tendencies”. He
even tries to strike up a partnership with Sideshow Bob, after he learns how much Bob
hates Bart too. If that doesn’t tell you all you need to know about this
guy, I don’t know what will. Next we have another famous criminal, Fat
Tony. As the head of the Springfield mob, Fat Tony is no stranger to some pretty serious
crimes. We first see him try to teach Bart the ways of being a mobster, and when
Principal Skinner goes missing and is assumed dead, Fat Tony tries to pin the whole thing
on this ten year old boy. Though he was innocent in that instance, other episodes
have shown that he isn’t above murder. He’s also frequently trying to manipulate people
like Mayor Quimby with his money makingschemes, and will threaten anyone he has to,
no matter who they are. Surprisingly, though he didn’t understand his son, Michael’s,
desire to be a chef, Fat Tony is still a decent father to him. Though this shows that
he isn’t totally heartless, it still doesn’t do much to help Fat Tony seem any more moral,
especially since Michael still ends up following in his footsteps. Though he may
be a bit of a mobster stereotype, his greed and willingness to blackmail
and kill are all too real. Next, we have monorail conman Lyle Lanley.
A sort of Music Man parody, Lyle does much more than simply steal three million
dollars from a city. With his manipulation tactics, he manages to convince the entirety
of Springfield (minus Marge) to let him build a monorail for them. Naturally, the
monorail is shoddy at best, driven by without a doubt the WORST choice for a conductor,
Homer Simpson. Though he doesn’t try to actually kill anyone himself, you could argue
that Lyle Landley is essentially putting dozens of monorail riders at risk of injury
and death with his uncaring and selfish nature. He clearly doesn’t care what happens
to the residents or the city after the monorail is built. Instead, Lyle is only
interested in taking the money and running. As if this wasn’t bad enough, Lyle was greedy enough
to do this scam with three other cities, with the aftermath being pretty bad, as we
see that North Haverbrook was pretty much abandoned and in ruins after their monorail
crash. He probably would have kept doing this scam too, if not for the fact that karma
finally caught up to him and he was beaten up by the same people he scammed. Though
he may be a charmer, we feel his cons can’t be overlooked or understated. Entering our top five, we have supervillain
Hank Scorpio. Oh boy, this guy was VERY hard to rank. On the one hand, Hank is
one of the nicest characters we meet. He’s respectful towards Homer and his family,
gives them numerous gifts and even tries to offer Homer advice. It’s no wonder that Homer
felt so happy and fulfilled in his new job. Buuuut on the other hand, he is LITERALLY
a James Bond-esque villain trying to take over the world. We see him kill a spy,
threaten the United Nations, destroy the Queensboro Bridge, and eventually, he even
manages to take over the East Coast after successfully fighting the U.S. Government.
So yeah, this guy is without a doubt a major threat… but he never ACTS like it. At least,
he doesn’t act like it towards his employees, being extremely generous with pay and benefits
and always being nice and lighthearted when interacting with them. If we’re looking
at only his actions, he’s on the level of Mr. Burns in terms of his crimes and his power.
If we’re looking at his personality, you could make a case for him being in the Grey or even
the side of Good. So yeah, it’s preeeetty complicated. Even so, we can’t exactly ignore
all the evil that Hank Scorpio has done, even if we may want to. So, we felt that placing
him within the top 5 was a goodcompromise, with his genuinely kind personality
preventing him from being put any higher. He’s a great boss, but not
necessarily a morally upright guy. Next, we have Sideshow Bob. Though you
may be able to make an argument that Bob is THE most evil character on the Simpsons,
what with all the murder he’s attempted over the years, there’s enough back and forth with
him that we felt like we could drop him a bit from the top spot. That being said, this
guy is still pretty evil. While wanting to kill Bart is his most infamous trait, he’s also
manipulative and has committed several other crimes along the way, from robbing the
Kwik-e-Mart, to election fraud, to identity theft. But as cruel and, let’s face it, criminally
insane as Bob can be, the guy still has a heart. He cared about his wife and son, and has
honestly tried to turn his life around at least a few times, even if it never quite works out.
He saved Springfield from being flooded and, despite the two of them being enemies,
Bob has also saved Bart a couple times, showing that he’s willing to push revenge
aside, if only occasionally. We also see him being friends with Krusty in the later
seasons, showing that there’s no hard feelings between them. While he may be just a bit too
far gone at this point to ever truly become good, those brief moments of goodness
are still something we can appreciate. Following Bob is his brother, Cecil Terwilliger. While not
nearly as famous as Bob, you could argue that Cecil is just a bit more
callous than Bob. When Bob genuinely tried to turn his life around, Cecil only took
advantage of him as a means of revenge. He was always jealous of his brother for getting
to be on the Krusty the Clown show, and decided to not only take that jealousy out
on Bob, but on Springfield as a whole. When he was hired to build a hydroelectric dam
for the town, Cecil purposely built the dam poorly so he could take the cash for himself,
not caring if he ended up flooding the town. When Bob and the Simpson kids tried
to stop him, Cecil in turn tried to blow up the dam in the hopes of killing them. Later
on, when Bob tries to fake his own death as part of another scheme, Cecil assists in it
alongside the other members of their family, showing that any jealousy or anger he may
have had towards his brother might have passed. Although Bob has certainly done
more crime than Cecil, Bob has also been seen regretting his actions and trying to
be better while Cecil doesn’t seem to mind being evil. For that, we feel we have
to place him just a bit higher up. Taking the silver medal is none other than
Mr. Burns. Honestly, what HASN’T Mr. Burns done. As a businessman, Mr. Burns puts
wealth and power above all else. He doesn’t care about environmental laws, or really any
laws in general, and certainly isn’t above resorting to bribery in order to get out of
punishment or getting what he wants. We see just how low he can go in “Who Shot Mr.
Burns Pt.1” where he essentially screws over the entire town in major and minor ways.
In his day-to-day life, he’s cruel towards hisemployees while his main business, the
Power Plant, pollutes the town. Burns also has a huge rivalry with Grandpa Simpson. We
see him use underhanded tactics to try and steal Jacquline Bouvier from Grandpa, and
then we see him try to kill both Grandpa and later Bart in order to get his hands on the
Flying Hellfish treasure. Not the first time he tried to kill Bart either, having run him
over in season 2 and then threatening to shoot Bart and Lisa after kidnapping their puppies,
which he wanted to make into a fur vest. Yikes... It was also Burns’ vendetta against
Mona Simpson that prevented Homer from having a mother, always getting in the way
of the two of them reuniting. Not only is Mr. Burns one of the most powerful villains
in the Simpsons, but he’s also the most personal, having betrayed, offended or
fought every single member of the Simpsons family on at least one occasion. But while
he can be one of the cruelest people in Springfield, Burns still isn’t completely
heartless. Occasionally, he’ll show concern and care for Smithers, even saving his life
in the episode “Midnight RX”. He’ll also sometimes choose to be nice, but often
change his mind or forget the lesson he’s learned, simply because it’s just not in his
nature to be kind or generous. For all that he’s done and is willing to do for the sake of his
own wealth and status, we feel that’s more than enough to give him
second place in our ranking. In our top spot, we have Russ Cargill.
While Mr. Burns and Sideshow Bob are the most prevelient villains in the series, Russ Cargill
took the spotlight in “The Simpsons Movie”. He’s described as someone who goes “mad
with power”, and when it comes to the environment, he’s willing to put his own ego
and the so-called safety of others above the lives of an entire town. He’s also connected
to the company that makes the dome that the government uses soooo let’s just add
financial greed on there as well. We see Russ become a lot more desperate after the
Simpsons manage to outsmart him and escape the dome, and when he sees that the residents
of Springfield are trying to escape as well, Russ decides to just blow them all up
instead of actually trying to, you know, do ANYTHING else. While trying to protect the
environment may sound good on paper, it sounds less good when you start to see
people - especially innocent citizens - as expendable. Russ also tries to kill both
Bart and Homer after they destroy the dome once and for all. Unlike Bob and Mr. Burns
who can occasionally show that they have a good side, no matter how small that side
of them may be, Russ literally has NO good side, and would’ve had a body count in
the thousands had he succeeded. He’s manipulative, self-serving and cruel, and
we can think of no one more deserving of our Gold Medal of Evil.
But what do you think? Let us know in the comments if you agree with our ranking. Be
sure to hit that notification bell and binge our Good to Evil playlist. Where we breakdown the
morality of the characters in your favorite cartoons, shows and movies. But
most importantly: stay wicked!
