Top 5 Episodes from each season of Simpsons cont...
Season 5
5. Rosebud - Mr. Burns longs for his lost childhood toy, Bobo.
I love the sequence that details Bobo's journey and how it ends up with Maggie...even though it's a little disgusting. Perhaps Burns trying to steal Bobo away from Maggie (ineffectively) is what set up her revenge moment in Who Shot Mr. Burns?
4. Boy Scoutz N the Hood - Bart goes on a squishee bender and ends up joining the few, the proud, the geeky: the junior campers. He actually ends up bonding with Ned Flanders, and feels only contempt for his dad, and then they end up on a camping/rafting weekend all together.
Before the Simpsons started doing basically half hour long musical episodes, the odd musical number in an episode really made it memorable. The “Springfield, Springfield” montage where Bart and Millhouse go crazy on super sugar squishee is pretty awesome. Homer is a giant idiot to a frustrating degree, but is nicely redeemed in the end.
3. Burns’ Heir - Mr. Burns has a near death experience and realizes he has no one to leave his considerable fortune to (Smithers gets buried with him…). A bunch of the children audition, and Mr. Burns ends up picking Bart.
“The lesson is: never try”, how can an episode with this motto go wrong? The actors that Mr. Burns hires to portray the Simpsons family is pretty gold, especially the guy who played Lisa (“he taught me about his Estonian heritage”).
2. Deep Space Homer - Homer ends up going into space as part of NASA’s effort to get more viewership.
I guess this episode is a parody of The Right Stuff, which I've never seen so I can't really comment on that factor. But I do love that Homer gets no respect at the plant...losing a popularity contest to an inanimate carbon rod (that, incidentally, deserves it more than Homer since it saved the astronauts from burning up in the atmosphere). "I for one, welcome our new ant overlords..." ah, so many good uses for that line. And, Barney's alcoholism is given a cause...it's kind of sad, actually.
1. Cape Feare - another Sideshow Bob episode, this time the Simpsons enter the Witness Protection Program to hide from Sideshow Bob.
I’ll admit, part of the reason I love this episode so much is a. the rakes, and b. the rendition of the H.M.S. Pinafore (“Very well, I will send you to Heaven…before I send you to Hell!”). Other awesome moments include the cringingly awkward scene where they FBI try to teach Homer his new name (in Simpsons sing-song theme voice: "The Thompsons"...).
(Dis)honorable mention: Homer goes to College: I actually really don't like this episode, and I'm not sure why. Well I can kind of tell why, it's because Homer acts, more than usual, like a giant dumbass...and is precisely the reason that later seasons of Simpsons are less palatable than classic episodes.