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1. Marge in Chains
Marge is definitely the most pleasant character within the Simpsons and so the comically exaggerated shunning she receives from her peers after accusations of shoplifting makes for an inspired episode with so many unexpected gags and one-liners with the unforgettable “juice loosener” kicking off the show. The episode has Bart imagining himself as the great “Bartina” a ploy with him in drag to seduce and then knock out the prison warden to help his mother escape prison and his father in Marge’s absence decides to wear a wedding dress with no one else to tell him to do otherwise. But the episode boasts a wonderful showcase of the late Phil Hartman’s talents with Lionel Hutz giving some of his best lines with the standout being “well, he's kind of had it in for me since I kinda ran over his dog. Well, replace the word 'kinda' with the word 'repeatedly,' and the word 'dog' with 'son'." If you need any further persuasion the episode ends with Marge receiving a statue of Jimmy Carter with her trademark beehive hair on it as a symbol of the community’s appreciation for the unjustly treated Marge.
"Cape Feare" and "Rosebud" are often categorised as the best episodes of the wonderful fifth season yet although this is deservedly so I always think "$pringfield" gets overlooked for whatever reason. All the jokes in the episode land and Mr. Burns' descent into madness upon the success of his new casino is just as great as him pining for his long lost teddy bear, it’s difficult to pick his finest moment here as he holds Smithers at gunpoint so he “gets in” to a model plane he’s made in a hilarious group of references to Howard Hughes, only heightened by the germs he sees multiplying everywhere telling him “freemasons run the country.” Then again you have the main plot of Marge’s unexpected gambling problem leaving Homer to actually fend for himself with the kids which goes hilariously awry as soon as Lisa mentions a nightmare she had about the bogeyman. Great writing all around from Homer’s deeply surreal “photographic memory” as well as his encounter with Rain Man to Grandpa Simpson moaning about how everyone wants something for nothing before he heads to social services and demands “I’m old, gimme gimme gimme.”
3. Bart’s Inner Child
What’s great about this episode is how all the characters finally get to let loose as they all fall for the new “do what you feel” movement after motivational speaker Brad Goodman (recurring antagonist Albert Brooks definitely more known for being the supervillain in "You Only Move Twice") and begin to act as rebelliously as Bart himself. The episode packs its punches quickly with a Wile. E Coyote send up as Homer attempts to get rid of his newly acquired trampoline off a very familiar looking canyon. It’s an inspired riff but apparently all Homer had to do was put on a bike lock on it if he really wanted to get something stolen as Snake immediately arrives to take the trampoline the minute this is put on.
4. The Front
This one gets in for its opening Itchy and Scratchy segment alone with its most ironically lame entry as Itchy tepidly hits Scratchy with a mallet to no real effect before both turn to the camera and tell the children watching “don’t do drugs” with a hilariously wise, knowing grin. The episode then gets its mileage out of Grandpa Simpson in his new job as a cartoon writer with epic lines like “Thank you for this award. It is a tribute to this great country, that a man who once took a shot at Teddy Roosevelt could win back your trust” and “Dear Mr. President, there are too many states these days. Please eliminate three. I am NOT a crackpot.” Homer’s subplot about retaking his High School science class is also great with this interchange probably being the best: Principal Dondelinger: Look, Homer, just take the test, and you'll be fine.
What’s not to like? And the show even ends on the pretend spinoff "The Adventures of Ned Flanders" which I’m sure we’d all watch forever.
5 & 6. Fear of Flying/ Marge on the Lam
A double bill of Marge-centric episodes that show her quirks and also give some of Homer’s most comically absurd moments. "Fear of Flying" starts with Homer being banned for life at Moe’s and looking for a new bar and which gives us a dark version of Cheers, the creation of Homer’s doppelganger Guy Incognito and the line “wait a minute, this lesbian bar has no fire exits, enjoy your death trap ladies!” Homer’s troubles lead to a free flight for him and his family but not to “freak states Alaska and Hawaii” and we learn of Marge’s phobia (and that Homer is deeply afraid of sock puppets.) What entails is no short of great as we see Marge completely lose it as she worries that “they never had a wedding for the cat and the dog, they’ve been living in sin” and we see her tragic discovery that her father was actually a flight attendant and that sometime in her childhood she was chased by a North by Northwest style biplane through a cornfield. However, in "Marge on the Lam" Chief Wiggum and Homer steal the show as they lose her in their Thelma and Louise inspired car chase when Ruth Powers turns off the headlights to Wiggum’s astounded “oh my God it’s a ghost car” and the two men end up doing the infamous canyon scene after a singalong to “Sunshine, Lollipops and Rainbows.” Also worth noting that the two episodes reveal Homer’s favourite song is the classic “It’s Raining Men” and his idea of ballet is a bear driving a little car.
7. Treehouse of Horror VII
This is for the episode’s third and final segment Citizen Kang which is a definite challenger to “The Shinning” as the best Treehouse of Horror segment as the aliens Kang and Kodos impersonate presidential candidates Bob Dole and Bill Clinton with ultimate deadpan that makes it a shame the pair can’t be involved in any other episodes besides the Halloween specials. Kang has one of the most shockingly funny lines with “abortions for some, miniatures flags for others!” which is a truly inspired way to win voters.
8 & 9 Lisa’s Rival and Summer of 4ft2
Lisa’s always been given the lesser focus for comedy throughout the show’s run, aside from the beloved “I am the Lizard queen!” duff gardens experience. Both these episodes give her much more to do and admittedly I have included the former mainly for Bart putting Milhouse on the FBI’s Most Wanted List, Homer’s Wizard of Oz homage “oh what a world” cry as his sugar melts in the rain, and Ralph’s classic “I bent my wookie.” On the other hand, "Summer of 4ft2" is a really emotional episode that earns great sympathy for Lisa if it already wasn’t there for all her loneliness. Watching her truly breakout in a completely different place as a new person is a fantasy many of us can relate to and it’s every bit as heartbreaking as Mother Simpson.
10. Simpsoncalifragilisticexpiala(Annoyed Grunt)cious
The title alone makes this episode worthy of being mentioned here but the show’s decision to put the bright optimism of this iconic British nanny into the hectic Simpson household is genius. The songs are pretty great with Shary Bobbins’ (“an original creation, like Rickey Rouse and Monald Muck”) advice to do everything the half-assed way to the beat of "A Spoonful of Sugar" being the standout. Other great jokes come from Homer suspecting every prospective nanny to be a man in drag after seeing Mrs. Doubtfire, the Itchy and Scratchy segment Reservoir Cats which is the most spot on Tarantino spoof I have ever seen, and the show’s incredibly dark ending as when Shary flies off she gets sucked into a jet engine which is one of the guiltiest laughs you could have watching the show.