The Simpsons might just be the most successful cartoon of all time. A huge cast of recognizable
characters, countless knock-offs and a crown which reads the longest running American primetime,
scripted television series. Whatever that means.
Cartoons were using violence as humor long before The Simpsons, something perfectly parodied
within the show, but the yellow-cheeked citizens of Springfield blazed the trail of twisted
comedy in a more family-oriented sitcom. Sure, it's got a lot of heart but it's the dark
vein at the show's core which always scratches that sinister, satirical and sometimes spooky
itch. I'm Kyle with WickedBinge. And these are our top ten darkest episodes of The Simpsons.
10. Hello Gutter, Hello Fadder What's an episode where Homer bowls a perfect game, and becomes
an overnight celebrity, doing in this list? Well, when Homer's spotlight quickly fades,
he crashes out. Hard.
Homer decide's he's peaked and pretty much his first instinct is to jump off of a tall
building. More on Homer's suicidal tendencies later.
Like so many one-minute wonders before him, Homer gets chewed up and spit out of the entertainment
industry. It�s ironic that the source of our enjoyment creates so much misery for those
involved but uh boo hoo, celebrities. We don't pay you to complain.
9. Mother Simpson The Simpsons loves a good fake-out and gives us one of the all-time
best when Homer stages his own death to get out of a highway clean up, kicking off this
episode. Slapstick turns to a real family drama when Homer's estranged assumed to be
dead mother shows up at his grave.
The show explains away Mona Simpson's years of negligence with an elaborate backstory,
and a post-office gag, but that doesn't change the profound affect that her absence has had
on Homer's life. Or the fact that his father chose to pretend she was dead rather than
tell Homer the truth. Talk about dysfunctional.
We really see Homer wrestle with deep feelings of abandonment and neglect in this episode
all common reasons for a life of low-motivation and alcoholism. Although there are definitely
heartwarming moments, Mother Simpson is one of the few episodes to end on a genuinely
somber note. Poor Homer. 8. Alone Again, Natura-Diddily Between seasons
ten and eleven, actress Maggie Roswell, the original voice of Maude Flanders, quit over
a pay dispute with the Fox Broadcasting Company. Show producers took the opportunity to axe
Ned's wife in well in about the least dignified way possible.
Reverend Lovejoy rubs some salt in the wound when he almost breaks the fourth wall during
his eulogy, summing up Maude as a supporting player in the lives of Springfield's residents.
It's a dark move in a dark episode that reaches its peak when Homer's pious neighbor practically
renounces his faith. Granted, the heresy doesn't last long God'll probably let you off this
time, Ned.
This one gets bonus dark points for putting a bird sanctuary in the middle of a speedway;
then it loses them for the feel-good ending. 7. The Secret War of Lisa Simpson Lisa has
an interesting role in the show's darker side. She's ostensibly good, hard-working and basically
the voice of order and reason to Bart's chaos. But at the end of the day, she's still just
an eight year old girl.
While it's admirable that Lisa volunteers for military school, her stubborn pride forces
her to endure the reality of a semester of loneliness and torment at the hands of the
other cadets. Kids can be seriously cruel and if you didn't know that, youve probably
blocked out large chapters of your childhood. Good luck in therapy.
Lisa's the only one who actually suffers for her pride this time, at least and the Simpson
siblings do come together in a touching display of solidarity. Still Lisa practically crying
herself to sleep listening to a tape of her mom singing? Pretty dark if you ask me.
6. Marge Be Not Proud The show tends to be at its most sinister when it shows storylines
from the kids perspectives. As a kid, everything hurts more, time passes more slowly and you're
more vulnerable in a world that barely respect you yet.
When Marge finds out Bart's been shoplifting, she's devastated but also struck with the
realization of innocence lost. Her subsequent coldness and reaction to her son is all delivered
to us through Bart's eyes, so we feel every pang of disappointment that much harder. It's
uncomfortable viewing.
Lawrence Tierney's infamous, but brilliant guest performance as Try-N-Save security guard,
Don Brodka, helps darken the mood as well. Despite the tearjerker ending, this episode
managed to convince us, just for a second, that truly unconditional love might not really
exist. Mom! � you love me right Mom! 5. Cape Feare I don�t know if it�s the
big feet, the British accent or the fact that he�s obsessed with killing a ten year old
boy but Sideshow Bob gives me the creeps. Actually, scratch that. It's definitely the
last one. And also the British accent.
This episode features a fully grown, convicted male making veiled and unveiled threats to
a child, including letters written in blood. Proving he's a man of his word, Sideshow Bob
ultimately makes an earnest attempt to brutally murder his target.
What makes the episode so twisted is just the sheer fixation that Krusty's former sidekick
has with killing his nemesis: The tattoos, the training montages and the extreme lengths
he goes to, following the Simpsons on their, admittedly lackluster, attempt to join the
witness protection program. Nice shirt, Homer. ('witness protection program' t-shirt. My
favorite joke in this episode!)
It also happens to be one the best, most memorable and funniest episodes in Simpsons history.
4. Bart Sells His Soul There's nothing strange about believing in souls. Hell, according
to statistics, there's nothing strange about believing in ghosts, with up to forty percent
of Americans accepting the existence of the ectoplasmic enigmas. It's hopefully less likely
that you believe a soul can actually be sold on a slip of paper although it remains a pervasive
trope in TV cartoons.
Kids will believe pretty much anything you tell them. Whether or not Bart truly loses
his soul in this episode is left unclear by the show's writers. But it's enough to make
Bart panic. It's definitely one of the more existential episodes, and no doubt it had
us all asking questions when we watched it as kids. What makes us who we are? Could that
really be taken away?
Bart's the perfect character to lose his soul, because the contrast is so strong between
his normal trouble-making, care-free self and his hollow, lifeless state. Top it off
with some frankly messed-up dreams and you've got yourself a nice dark slice of existential
crisis. Thanks for shaking us to our cores. 3. Homer's Odyssey The older Simpsons episodes
are a lot rougher around the edges. The timing is different, the animation is jerky and the
voices are scratchy. While they may hold some of the greatest Simpsons moments, it's doubtless
that their overall vibe is just a little darker to begin with.
While the show's writers blew one of the best options for an episode name after just three
weeks, on a plot that's barely related, they did succeed in creating one of the most poignant,
and darkest, Simpsons tales to date.
In the episode, Homer suffers humiliation in front of his son's classmates, loses his
job and decides to kill himself, almost getting his family killed in the process. When he
eventually achieves success in his public safety campaign, he ends up selling out the
cause to go back and work for the evil Mr. Burns.
The corporate submission and suicidal themes really remind us that The Simpsons started
out as a pretty radically different, satirical cartoon with darkness in its DNA.
2. My Sister, My Sitter We've talked about the darker side of Lisa's pride already. In
My Sister, My Sitter, we see what happens when Lisa faces the threat of failure, and
just how dangerous her pride can be to others.
During childhood, sibling relationships pretty much just follow the law of the jungle. We're
talking about ten to fifteen years of anarchy. The only vague, objective hierarchy is age.
You're older, you're the boss.
When Lisa demonstrates her responsibility, Homer and Marge upset the natural order by
putting her in charge for the evening, to devastating effect. Bart effectively turns
into the kid from The Omen and Lisa almost suffers a nervous breakdown, terrified of
ruining her newly acquired reputation as a babysitter.
It all culminates in Lisa wheeling an injured, unconscious Bart, and a caged Maggie, through
the bad part of town, late at night, before tumbling into a river.
Everything about this episode is disturbing. It has a serious message about the harmfulness
of pride, for which Lisa's goody-two-shoes persona is the perfect vehicle. Kids constantly
suffer the cruel irony of feeling a need to prove themselves in a world that will never
respect them. It doesn't matter what you do: if you're a kid, you're just a kid. But that
reality still bites. The Simpsons perfectly captures the power struggles of childhood,
time and time again. This dark episode might just be the pinnacle of that achievement.
1. Homer's Enemy Yep, you probably guessed it already. Frank Grimes is one of the show's
most memorable characters, to the point where he's almost transcended and become a term
in common language. Refer to someone as a Frank Grimes or The Frank Grimes
of X and chances are, they'll know exactly what you're talking about.
In a sense, Frank Grimes represents our biggest, most secret fear of all: The fear of being
unlucky. We all get in car, cross the street or ride on a plane and rationalize that, for
the most part, it�s a pretty safe thing to do. But deep in the back of our minds,
we know there's always a possibility of something happening, completely out of our control,
to end our fragile existence.
The episode starts by setting up Frank Grimes as the guy who never gets a break. It's a
dark beginning� and then it gets way weird. Throughout the episode, Frank becomes increasingly
frustrated at the injustice of Homer�s comparative success and happiness. Before long, he goes
completely insane and� well, immediately succumbs to the doom he�s been narrowly
avoiding his whole life.
Is it a sad episode? Not by a mile. In fact, it�s one of the funniest in the show�s
run. That contrast is exactly what makes this our darkest episode. It rings so true� though
we all like to believe that we live in a meritocracy, rewarded for our efforts, isn�t it really
just a cruel mix of nepotism and� blind luck? Is Frank Grimes the show�s way of
shining a light on the miserable reality of ou- (insert �change the channel marge�
clip)
Anyway, things were getting too dark. What episode of The Simpsons do you think is the
darkest? Let us know in the comment section. If you enjoyed it, please remember to like
this video, subscribe and hit that notification bell. But most importantly, stay wicked.