15. Marge Is Disappointed In Bart // Marge Be Not Proud (S7E11)
A mother’s disappointment is a terrible thing and after Bart is caught stealing a video game by the store security he thinks he has managed to prevent Homer and Marge finding out. However, on a trip for their family Christmas portrait, Bart is accosted by the same security guard and Marge learns of Bart’s attempted thievery. She stops treating him as a kid and pays little attention to him if he’s wants to be a petty thief. Wrapped with guilt Bart tries to earn his mother’s forgiveness with an early Christmas present. This one used to make me feel awful when watching it, imagining the guilt and shame.
14. Maude Dies // Alone Again Natura-Diddly (S11E14)
During a t-shirt firing at a racing car event, Maude is knocked off the top of the stand by a barrage of shirts. She’s pronounced dead at the scene and it is one of the first times a main character from The Simpsons was killed off permanently. We see a distraught Ned coping with the loss of his wife throughout the episode and he starts to question his faith as well.
13. Bea Dies // Old Money (S2E17)
An unhappy Grandpa Simpson meets Bea Simmons at the retirement home after they have been given each other’s pills. Upon seeing her, Grandpa instantly falls in love with the two of them spending a montage of dancing, sharing a shake and walks on the beach to the tune of ‘Embraceable You’ by Frank Sinatra. Grandpa’s plans for Bea’s birthday are interrupted when Homer says it’s their “third Sunday of the month” which is the family’s time to spend with him.
After being mocked by Homer and taken on an over-extended safari trip, Grandpa gets back to the retirement home to learn in his absence, Bea passed away and believes it was of a broken heart. At the funeral, Grandpa’s rage gets the better of him, exclaiming “I have no son” and Homer spends the rest of the episode trying to gain his dad’s forgiveness.
12. Lisa Is Alone On Her Birthday // Stark Raving Dad (S3E01)
Wait… what do you mean there’s a Simpsons episode with Michael Jackson in it and you can’t find it on Disney+? The episode opens up with Lisa exclaiming how she does so much for Bart and asks him for a present for her eighth birthday. Bart agrees he will get her one. However, in a series of events including Homer being sent to an insane asylum where he meets ‘Michael Jackson’, telling Bart ‘MJ’ will be coming home with him and getting the whole town into a frenzy, we see Lisa alone at the table on her birthday with the exception of Maggie, crying and singing ‘Happy Birthday’ to herself. A very solemn moment in the show.
11. Maggie’s First Word // Lisa’s First Word (S4E10)
In one of the many flashback episodes we learn about Lisa’s birth to her first word after the family have tried to get Maggie to say her first word. By the end of this quaint episode we see Bart and Lisa arguing. Homer removes himself from the situation by taking Maggie to bed to which he says “The sooner kids talk, the sooner they talk back. I hope you never say a word.” He leaves the room and we see Maggie remove her pacifier to say “da-ddy.” This is adorable as both Bart and Lisa previously addressed Homer by his name and shows the kind impact Homer has had on Maggie.