The Simpsons was always a sadistically funny show with the whole town full of sociopathic jerks. There are times however, where the Jerkass characters and villains go too far...
- Sideshow Bob in all of his appearances tried to kill Bart, as well as committing other villainous acts such as in "Sideshow Bob's Last Gleaming", when he tries to atom-bomb the entire city just so he can get rid of television. But he finally crosses the line in "Funeral for a Fiend" when he decides to get people to hate Bart while he's on trial, fake his death, and, with the help of his whole family, burn Bart alive in a coffin being pushed into a furnace. Fortunately, he is caught and is sentenced to 87 years in prison along with the rest of his family. Strangely, the earlier episode where he hypnotized Bart into being a suicide bomber had him sentenced to death at the end but the sentence wasn't carried out with no explanation why.
- Even before that, he crossed it in his second appearance. While his first crime can be justified by his shabby treatment by Krusty being a mockery of everything he believed children's entertainment should be, his second appearance has him use Selma as a ticket out of prison and then cutting off the loose end by murdering her on their honeymoon. Unlike Krusty, Selma hadn't done a single thing wrong to him and was just a lonely, if abrasive, woman. And this was before he tried to kill her nephew Bart, who he at least had a reason to hold a grudge against.
- The Kindergarten Teacher's treatment of Bart, as seen in "Lisa's Sax". SHE IS THE REASON why Bart is the troublemaker he is today. Bart was actually looking forward to his first day of school, but this teacher started belittling him for no reason other than sheer malice. What makes it worse is that Bart was just 5 years old and her actions (among other things) made Bart actually consider suicide. She also faces no consequences for her psychological and emotional abuse of a toddler whatsover. The teacher basically wrote off Bart as a lost cause because he didn't catch on to things as quickly as the other kids:Bart: (singing) B-I-*clap*-*clap*-*clap*-O and Bingo was his name-o.
Teacher: (writing on a clip board) Added extra clap; not college material.- Case in point "I Married Marge" showed Bart setting fire to Homer's tie at only six minutes old, and "War of the Simpsons" had Bart try to run over his babysitter with the family car. On top of that, "Lisa the Simpson" reveals that Bart actually was a smart student until the Simpson gene made him dumb, and other episodes like "Bart Gets an F" and "A Test Before Trying" show that Bart can be smart when the plot calls for it). Fortunately....
- In "Separate Vocations", Snake tries to run over Bart when he's with Eddie and Lou in a ride along. In “Realty Bites,” meanwhile Snake attempts to brutally decapitate, and later simply snap the neck of Homer for the great crime of legally buying his repossessed convertible, Lil’ Bandit.
- In "The Crepes of Wrath", Bart is treated like a slave by two mean winemakers in France. At first, this is amusing, as we see Bart get what's coming to him for his brattiness. However, it fades when you see Bart sleeping with nothing but a blanket after reading a letter from his mother as the abuse he is suffering begins to sink in. When the winemakers finally force Bart to drink wine doctored with antifreeze, putting him in real danger of being killed or blinded, the winemakers cross the line and all your sympathy goes to Bart, which makes his eventual escape and revenge all so sweet.
- Cecil Terwilliger absolutely crosses this in his first appearance, "Brother from Another Series". He conned his way into building a dam, cut back on the building materials to embezzle the funds, and then tried to kill Bart, Lisa, and his own brother in an attempt to blow up the dam, and the dam floods the town anyway because of the lackluster construction. The only reason no one was killed was because the universe dips into cartoon physics at that point. While he privately admits he did all this to get back at Bob for becoming Krusty's sidekick, he's more than happy to claim he did it for the money.
- Joe LaBoot from "The Boys of Bummer" crosses the line when he starts to encourage the rest of the people to harass Bart into the Despair Event Horizon (after initially sympathizing with Bart before realizing who he was talking to). Worse still, not only is LaBoot a massive hypocrite who made the same mistake that Bart did, but it is implied that other children were also attacked before with similar results, giving LaBoot a body count. Given all of this, it becomes rather amusing when Grandpa Simpson belittles LaBoot.Abe: "You stink, LaBoot!"
- In The Simpsons Movie, Russ Cargill crosses it when he tricks President Schwarzenegger into authorizing the fiery destruction and total obliteration of Springfield. Cargill knew damn well what the options were that he gave the President, and even manipulated him into choosing the Nuke 'em option.
- Even though he's normally Laughably Evil, there have been times where Mr. Burns crosses the line to straight up evil.
- In "Brush with Greatness" Mr. Burns mocks Homer's weight loss success by calling him "the fattest thing he's ever seen". That's the point where Marge decides there's no inner beauty in Burns and kicks him out.
- "Who Shot Mr. Burns? (Part 1)" is a long string of evil deeds committed by Mr. Burns. While stealing Springfield Elementary's newfound wealth is pretty bad, and trying to block out the sun so the town will have to use his electricity nonstop is supervillain evil, the two cruelest things Mr. Burns does is hit Santa's Little Helper with a full blast of oil from an oil rig then mock him for it, and firing Smithers, his most loyal toady. It's no wonder when he's shot that Everyone Is a Suspect.
- In "Raging Abe Simpson and His Grumbling Grandson in 'The Curse of the Flying Hellfish'", having already stolen the contents of the tontine from Abe Simpson, Mr. Burns kicks Bart into the safe which falls into the ocean, just to spite his grandfather Abe.
