1. The Way We Was (Season 2, Ep 12)
After the TV set breaks, the Simpsons decide to tell the story of how Homer and Marge met. The episode is a flashback and we get an interesting look at what Homer and Marge were like in high school. Of course the sparks fly right away, but there is conflict and drama to face before the iconic couple finally realize they’re meant for each other. It’s sweet, it’s funny, it’s touching, it’s a great episode.
2. Lisa's Substitute (Season 2, Episode 19)
Lisa is immediately smitten when a dreamy substitute teacher, Mr. Bergstrom, (voiced by Dustin Hoffman) comes to Springfield. He’s deep, he’s intelligent, he’s sensitive, he’s everything Lisa every wanted in a male figure but never had. The heart of the episode comes not only from Lisa’s relationship with Mr. Bergstrom but also the relationship between her and her and Homer, as she has to learn to accept him for who he is. The episode is about Lisa’s growth as a character with the ending cementing this growth in one tear-jerking picnic.
3. Krusty Gets Busted (Season 1, Ep 12)
Bart is in denial after his hero, Krusty the Clown, is arrested for armed robbery. Although everyone has accepted Krusty’s downfall and embraced his side kick Sideshow Bob (who makes his first appearance in this episode), Bart is determined to prove Krusty’s innocence. With the help of Lisa and Maggie, Bart embarks on a mission to clear Krusty’s name. The story is exciting, offering many twists and turns as well as a genuinely surprising ending. IT’s also worth mentioning that this episode was directed by animation legend Brad Bird, who directed The Incredibles and Ratatouille, so that alone makes the episode worth checking out.
4. Kill Gil Parts I & II (Season 18, Ep 9)
Although this an episode after The Simpsons’ golden years, it’s still really, really funny. A deadbeat named Gil comes to live with the Simpsons, and Marge has to grow a pair and ask him to move out as he far outstays his welcome. Gil is such a pathetic bum that it’s hilarious, in the best way. His impact on the family drives the comedy and Marge’s character development. It’s also Christmas themed- so now is a great time to watch it!
5. Homer’s Enemy (Season 8, Ep 23)
This is perhaps the darkest episode of the series. When Frank Grimes, a man who’s had to work had for everything he got, comes to Springfield the tables turn. Frank is obviously the polar opposite of Homer, who’s successfully coasted through life. He tries to call Homer out on this, but his efforts are to no avail. Homer keeps getting rewarded for his minimal efforts while Frank can never catch a break. The ending is one of the series most morbid, which is very different from the usual optimistic Simpsons ending. The dark, ultra-realistic tone of this episode sets it apart from the rest of the series, making it a must see for Simpsons fans.
6. Behind the Laughter (Season 11, Ep 22)
The Simpsons do a parody of VH1’s wildly popular “Behind the Music”, even getting the narrator from the show to narrate the episode. The episode is full of hilarious forth wall breaks and mockumentary style interviews that detail the over the top turmoil that was going on behind the scenes of the Simpsons. It’s such a different episode and employs a whole different kind of comedy. This out of genre episode is just as funny as it sounds.
7. And Maggie Makes Three (Season 6 Ep 13)
The Simpsons decide to tell the story of how Maggie came into their lives. Homer was living his dream of working at the bowling alley when Maggie came along as an unexpected surprise. The episode can be both emotional and dramatic, detailing how Homer had to quit his dream job in order to support a third child. But the ending and the payoff are just beyond sweet, as we see just how much Homer loves Maggie.
8. Stark Raving Dad (Season 3, Ep 1)
I kind of need to put this episode on my favorites list, considering that it’s a really good parody of my all-time favorite film, One Flew Over the Cuckoo’s Nest. The parody here is not only accurate but also funny. Homer, while committed in a mental hospital, meets a man who thinks he’s Michael Jackson, and he’s actually voiced by Michael Jackson, and of course, he sings! So yeah, it’s kind of hard not to love a One Flew Over the Cuckoo’s Nest Michael Jackson episode.