If I was to write this list completely objectively, it would basically just be, “Things Moe Szyslak Has Said.”

There are so many words that can be used to describe the humor of The Simpsons — smart, stupid, silly, subtle — but what about existential? What about soul-crushingly sad? Or what about a simple, succinct, “dark”? Every now and then, the writers of The Simpsons break out a line so devastatingly depressing that it catches us unaware and sends us into a thousand-yard, black-and-white-flashback stare that makes us wonder whether this is the same show that once made one of the greatest episodes in TV history about a guy and his snow plow.

Here are a handful of the Darkest Lines ever uttered on The Simpsons, weighted against a certain surly barkeep whose suicidal quips could fill a Russian novel. Starting with…

7 “Your Uncle Arthur used to have a saying: ‘Shoot ‘em all and let God sort them out.’ Unfortunately, one day he put his theory into practice. It took 75 federal marshals to put him down. Now let’s never speak of him again ”

Marge may have not managed to help Bart out with his moral quandary in “The Boy Who Knew Too Much” with this unexpected avuncular anecdote, but she did help us understand the dysfunction of the Bouvier family a little better. Though she vowed never to speak of Uncle Arthur again, moments later, she does finally point Bart in the right direction by telling him to listen to his heart, and not the voices in his head “like a certain uncle did one gray December morn.”

6 “Yeah, that sniper at the All-Star Game was a blessing in disguise!”

Obviously, Moe couldn’t be left off the list entirely, and his assessment of the Springfield Isotope’s success is, at least, a bit of dark humor not directed at himself for once. 

5 “Homer, you’re dumb as a mule and twice as ugly. If a strange man offers you a ride, I say take it!”

Abe Simpsons isn’t known for his nurturing abilities, but, along with calling Homer an accident out of anger, this might be one of the lowest points in his parenting career. Telling your own young son to actively seek out a kidnapping is downright sadistic. Lousy traumatic childhood.

4 “Change the channel, Marge!”

Homer’s half-asleep outburst at the funeral of Frank Grimes — or Grimey, as he definitely did not like to be called — capped off one of the darker storylines of the Simpsons Golden Age when Homer was so incompetent that it drove the unluckiest man in Springfield to his death.

3 “Not today, old friend. But don’t worry, the holidays are just around the corner”

If we’re going to give Moe one singular suicidal one-liner, this has got to be the one. The entirety of “Whiskey Business” was dedicated to uplifting the perpetually depressed Moe, but after blowing his chances at surprise stock-market success, there was real reason to worry when he went into that closet. 

2 “The Day of the Gun-Toting, Disgruntled Postman Shooting Up the Place went out with ‘The Macarena’”
“Well, I’m just glad I work at an elementary school”

The only reason this line didn’t land at the top of the list is that, in 1999, crazed gunmen weren’t quite as universally associated with American elementary schools as they are today. In 2023, this one might not even make it past the censors.

1 “I might go mad with fear out there, so, Todd, I want you to shoot daddy if he tries to get back in”

When Flanders lets the entirety of Springfield into his bomb shelter out of the goodness of his heart, it was inevitable that his selflessness would be the end of him — or so it seemed. Though the only thing the chihuahua-head-sized comet managed to annihilate was the shelter itself, Flanders’ instructions to his youngest son on killing his own father is the bleakest The Simpsons ever got.

Scroll down for the next article