Reposting since I'm a fag.
I'm a big Simpsons fan, and I want to show some anons who aren’t familiar with the show some of my favorite episodes in case they’d like to get into it. Feel free to share any other episodes you think are essential for understanding the context (or characters) of the upcoming season.

Homer related: Homer Goes to College (s5e3), Homer the Vigilante (s5e11), Homer the Great (s6e12)
Bart related: Bart's Comet (s6e14), Itchy & Scratchy: The Movie (s4e6)
Marge related: Marge vs. the Monorail (s4e12)
Krusty related: Krusty Gets Kancelled (s4e22)
Family related: Itchy & Scratchy Land (s6e4)
Flanders related: Homer Loves Flanders (s5e16)
Burns related: Rosebud (s5e4)
Sideshow Bob related: Cape Feare (s5e2)
Springfield related: Who Shot Mr. Burns? (Part One and Two) (s6e25 & s7e1), 22 Short Films About Springfield (s7e21)
Any Threehouse of Horror episode.

Other anons here mentioned Barts Birthday, Bart sells his soul, King-size homer, Bart gets famous, Angry dad: the movie, and Weekend at Burnsie's.