Unexpectedly Dark Episodes of The Simpsons.
- "Homer's Enemy" is a story focusing on Frank Grimes (a "realistic" character, by Word of God) being forced into the Played for Laughs Crapsack World of Springfield and getting so fed up with Homer's Idiot Houdini luck that he becomes the titular "enemy" of Homer... and then when Homer's luck saves him from being humiliated by a plan of Grimes, he undergoes a Villainous Breakdown which ends with him accidentally committing suicide-by-high-voltage.
- "The Boys of Bummer" gets a special mention. The entire population of Springfield abused Bart simply over a lousy baseball game. And they did not stop abusing Bart, even when he was Driven to Suicide (they even egged him on when he tried to kill himself). Not even Bart falling into a coma stopped them from continuing to mock him. They continue to verbally abuse him until Marge furiously puts the entire town into shame for their cruelty towards him.
- Any episode with a character who has no funny quirks and is played seriously. Examples include the French winemakers from "The Crepes of Wrath" (who nearly killed Bart by giving him antifreeze-laced wine not to mention that their general treatment of him was pretty poor), the Babysitter Bandit from "Some Enchanted Evening" (who tied up the kids and tried to rob the house) and Bart's kindergarten teacher from "Lisa's Sax" (whose treatment of Bart made him what he is today).
- Some episodes with Mr. Burns are darker and more dramatic than most other episodes. Examples include "Raging Abe Simpson and His Grumbling Grandson in The Curse of the Flying Hellfish" (where he tries to drown Bart), "Who Shot Mr. Burns? Part One" (where he blocked all the sunlight from Springfield, and screwed over several other characters, all of which is played seriously enough to make his shooting look justifiable), "Mother Simpson" (where he was involved with biological warfare and is responsible for forcing Homer's mother, Mona Simpson, to run from the law, even though she saved him), and "The Great Phatsby" (where he is betrayed by a superstar hip-hop artist who idolizes him, and schemes to get revenge on him). Mr Burns' actions also set future episodes in motion...
- "Cape Feare" has Bart sent a death threat in the mail; the words "I'M GOING TO KILL YOU" written in blood. He spends the rest of the day paranoid about who could be trying to kill him, but eventually learns that it's Sideshow Bob. The Simpsons go under witness protection, change their name, and relocate to a houseboat, although Sideshow Bob continues to chase after him. That night, Bob ties up the family and traps them, with the exception of Bart, whom he chases after with a knife. Bart only makes it out alive at the end because of some Bond Villain Stupidity on Bob's part. Despite this, it's considered one of the funniest episodes of the series.
- "Hurricane Neddy" is about the Flanderses' house being destroyed by a hurricane and Ned going crazy, shouting at everyone about their biggest flaws. It also reveals that Ned's Verbal Tic is due to years of repressed anger due to his parents, who would never punish him.
- In "Alone Again, Natura-Diddly", Maude Flanders is Killed Off for Real when she is shot by a T-shirt cannon, is knocked over the railing of a speedway spectator stand, and falls to her death. Both Ned and his kids are devastated, with even Bart feeling bad for them. Homer attempts to get Ned back into dating, although he still feels uncomfortable with it. While the episode has a slightly upbeat ending where Ned meets a Christian musician he likes, it's later revealed that their relationship didn't work out.
- "Homer's Odyssey" from season one has Homer attempt to commit suicide because he feels that he's failed his family by not finding a job after getting fired (for the first time). Outside of two elderly neighbors cracking a joke about Homer "...taking his rock out for a walk," the situation is not Played for Laughs. Thankfully, he doesn't do it and instead decides to become a safety advocate after saving his family from being run over on a dangerous street, but it's still rather shocking.
- One unexpectedly dark Couch Gag features the entire family except for Bart dying in morbid ways; Homer chokes on the radioactive rod he's handling, Lisa somehow breaks her neck after bumping into a wall and getting hit in the head with her saxophone, and Maggie actually gets to drive the car, taking her and Marge off a cliff, through a barn, and into a lake — with Marge's dead body actually floating to the surface. Bart comes home to an empty house, but doesn't seem to mind because it means he gets the remote to himself.
- In "Sleeping with the Enemy", Lisa gets anorexia because she thinks her butt is big. And this arc doesn't have a happy ending, with Lisa saying that she still struggles with it and it might last for years to come. Her sadness in "Moaning Lisa" and "Lisa Goes Gaga" is also eerily similar to clinical depression.
- Downplayed for "One Fish, Two Fish, Blowfish, Blue Fish" and "Homer Simpson in: 'Kidney Trouble'", which both have a character believe they are going to die but zigzag between Black Comedy and playing it seriously. In the former, Homer eats a blowfish and is told he may be dying. There are jokes like him getting Sequential Symptom Syndrome with the five stages of grief, but also serious moments like Marge dealing with her husband's possible death. In the latter, Grandpa needs a kidney transplant but Homer chickens out. There is comedy in scenes like the cause of the kidney failure being holding his pee too long, but his situation is played very seriously.
- "Lisa's Sax" is Season 9's entry in the tradition of Flashback episodes and starts, as the title indicates, with Homer and Marge telling the story of how Lisa got her saxophone. However, to get there they have to reveal the history of Bart's first experiences in school, which turns out to be his Start of Darkness, as a Sadist Teacher crushed his spirit before he was out of kindergarten. When Homer and Marge went to school psychologist Dr. Pryor in an effort to get help with Bart, who had alarmed Marge by drawing a picture of himself being stabbed with knives, Pryor determined that Lisa was gifted; as a result, Homer eventually bought Lisa her saxophone because it was the only way to encourage her talents that he could afford. Bart continued to be left to his own devices and learned to cope by becoming the Class Clown he is today.Dr. Pryor: Marge, Homer, I believe your Lisa may be gifted.Marge: That's wonderful. But still, can't you do anything for Bart?Homer: Marge, he's five. His life is over. Lisa's the wave of the future!
- "Pixelated and Afraid" has Homer and Marge stranded in the wilderness and in very real danger of being killed, which is a sharp contrast from the Amusing Injuries and other gags the show is usually known for doing.
