Tear Jerker / Dark Simpsons

• "Lisa It's Your Birthday". Lisa is informed by Wiggum that her parents and her brother were killed the day before her birthday. The next day she goes to their funeral were beside her, nobody else attended to comfort her and ends up "celebrating" her birthday and breaking down in front of Maggie.
• "Do It For Maggie" and its remake "Homer Can't Let Her Go". Marge is murdered but Maggie survives. Homer hits the Despair Event Horizon hard and kind of starts to lose it, prompting Lisa to run away to live with Mr. Bergstrom when Homer creates a substitute for Marge with a plant traumatizing the girl and Bart to commit suicide by drowning. Homer resolves to work hard for Maggie because she's all he has left, but the ending implies that he's considering suicide himself (the maker of the video leaves it intentionally vague as to whether he goes through with it).
  • Homer instantly attempted to commit suicide on the night Marge was killed, but as he was about to do it, he remembers a memory of the prom he had with Marge.
  • At school, Lisa and Bart have an awful time with Lisa dealing with a P.E. teacher who berates her for being sad due to her mom's recent passing and Bart hallucinating Marge visiting his class, only for her to fade away.
  • Bart looks out the window and becomes jealous of Rodd and Todd's loving dad, while all he got are memories of Homer abusing him on his photo album.
    Bart: That's probably never gonna happen.
  • The reason for Bart committing suicide is expanded upon in the remake, and yes, it is worse: After being attacked one last time by a furious drunk Homer about finding out about his replacement big brother, Bart empties the room and burns his childhood away, then kills himself by drowning at the sea. This makes Homer realize how much his addiction to Duff's beer drove his older children away from him, giving it up lately for the sake of Maggie's well-being.
  • Homer considers suicide three times in "Homer Can't Let Her Go": at the night when Marge was killed, when he discovers that Bart has replaced him with a big brother as he was searching for Lisa, and at the end of the episode, looking completely miserable in his room watching tv as a hang is tied near his ceiling.
• In “Where’s Maggie Simpson,” Maggie climbs out of her window at night, and gets mauled to death by a tiger at Burns’ casino. Marge is so overwhelmed with grief that she commits suicide by sticking her head in the oven. That’s not the saddest part, though. The saddest part is that Homer expresses his grief by putting pictures of Maggie up all over his work station, covering up the words “don’t forget, you’re here forever” in such a way that the message becomes “do it for her.” What was perhaps the most famous heartwarming moment in the original show instead becomes depressing and morbid.
• In "The Story of Homer and Lisa", Homer dies due to working at the Nuclear Power Plant for eight years. Homer's final goodbye was in an envelope to Lisa, set to the good times Homer and Lisa had as father and daughter, which also somewhat doubles as a Heartwarming Moment.
  Homer: Little Lisa, Lisa Simpson. You know, I always felt you were the best thing my name ever got attached to. Since the time you learned to pin your own diaper, you've been smarter than me. I just want you to know I've always been proud of you. You're my greatest accomplishment and you did it all yourself. You helped me understand my own wife better and taught me to be a better person. But you're also my daughter. I don't think anybody could've had a better daughter than you—
  Lisa: Dad, you're babbling.
  Homer: See? You're still helping me.
• The way "Bart Jumps the Springfield Gorge" recontextualizes Homer's comedic fall into the gorge by having Bart die attempting the stunt, Homer in mourning, then committing suicide in a way that pays tribute to Bart.
  Homer: (skating down the ramp) Hold on, son! I'm-a comin'!
• In "Marge Simpson's Fear of Flying" not only Marge's fear came true, but after surviving the crash she completely breaks down after being forced to eat her dead children in order to survive
• "Murder at the Simpson House" had Groundskeeper Willie kill the kids and take them away. Homer and Marge look for their missing kids until Willie is brought to justice. With the kids dead, the parents realize the passion is gone from their marriage. One night, Homer returns home in an attempt to rekindle their love, but Marge had already left, leaving behind their wedding video taped over by her farewell message. Cue the haunting shot of Homer staring at the starry sky from "Mother Simpson".
• In "The Bus That Couldn't Slow Down", Bart, Lisa, and many children die in a bus crash accident. Homer and Marge don't take the news well, with the video ending with Marge unable to sleep due to grief and Santa's little helper sleeping near the door, waiting for his master who will never return to the home.
• In "Bart Wets His Pants", Homer causes Bart to wet his pants in a football stadium, humiliating the boy in front of everyone, making the poor boy a laughingstock in his town, with his former friends abandoning him to torment him and even his own family joining the massive bullying. This causes the poor kid to have nightmares of his family tormenting him, and finally commits suicide when Homer wets his pants and mockingly compares himself to Bart. The poor boy doesn't even have a proper burial, as everyone laughs at his funeral when Lenny makes a tasteless joke about the boy.
• "Homer Loses Everything" is Exactly What It Says on the Tin, and as you can imagine, it's a surprisingly heartwrenching story. Homer is just coming home for the day when he sees his daughter Lisa needs help getting her basketball free from the hoop above the garage door. Homer's response is to start shooting at it, and some of the bullets whiz by a passing fighter jet which mistakes him for an Iraqi terrorist and launches a Hellfire missile at his house. Homer manages to escape the explosion, but his entire family is killed in the blast. This sends him into a deep depression that leads to him getting heavily drunk in a futile attempt forget his woes, driving out from the bar only to start hallucinating his children with expressions of sadness in the backseat, and finally turning violent when the cops attempt to pull him over, killing numerous trick-or-treating children on the sidewalk in a psychotic rage. It all ends with him crashing his car to a halt and being rammed into by numerous emergency response vehicles, causing a tremendous vehicle pile-up on the highway and supposedly killing Homer in the process.