Darkest Modern Simpsons Episodes

#	Title	Image	Release Date
6	Whiskey Business		May 5, 2013
5	Lisa the Drama Queen		January 25, 2009
4	Alone Again, Natura-Diddily		February 13, 2000
3	Co-Dependent's Day		March 21, 2004
2	Dial 'N' for Nerder		March 9, 2008
1	Flander's Ladder		May 20, 2018

Honorable Mentions

Title	Image	Release Date	Why It's Not on the List
Frying Game		May 19, 2002	"This ending moment before the fake-out is really, really black! I specifically remember being horrified, but then faked out by the game show ending. After Homer and Marge are accused of a murder they didn't commit, Homer almost ends up getting the electric chair. While it has clever writing and an interesting story, The Frying Game has a twist that's certainly out of left field, and I can see why some people would feel a bit disturbed at the ending."
The Scorpion's Tale		March 6, 2011	"The concept of this one is very honest about some elderly struggling to find happiness late in to their lives, to the point that apparently, every elderly in Springfield is willing to drug themselves with experimental opioids, even if it means their popping out. And my jaw drops every time I see these eyeball scenes. It's just... eugh!"
Paths of Glory		December 6, 2015	"While I hope this doesn't sound ecogentric, this episode almost felt like a nod to my Worst Simpsons video question. The writers address my question: Is Bart a psychopath? And apparently, no. Based on previous seasons, you could definitely have fooled me. But I think as of this episode, the writers called their jet service on just how callous Bart could get to the suffering of others. Bart's basically put in a ward for child psychopaths and is encouraged to kill soldier in a war shaped as a video game. Unlike the other psychopaths, though, it turns out he's not interested in killing people. Well, I'm glad to hear it."
Boys of Bummer		April 29, 2007	"I talked about this one before in my list of Worst Simpsons Episodes, and it's indeed one of the darkest Simpsons episodes; and in my opinion, also one of the worst. Just seeing how cruel everyone is to Bart throughout the entire thing is pretty unpleasant to watch. Bart takes part in a baseball game, and after missing the ball, he ends up costing everyone the game. But this, and this alone, the town begins to ridicule him, mock him, and shame him, to the point that Bart becomes suicidal. As I've said, the Simpsons is no stranger to dark humor, but I've personally never found anything funny or clever about this episode. It's mostly just cruelty for the sake of... bad writing, I guess?"