#10 - S05xE02: Cape Feare
Bart's nemesis, Sideshow Bob (voiced by Kelsey Grammar), gets out of prison again and has been out to kill Bart ever since Bart cracked Bob's framing of Krusty The Klown and every other scheme since. Following a parody of the film Cape Fear, The Simpsons are put into Witness Protection, renamed The Thompsons and move to Terror Lake. Unfortunately, Bob follows them and the climax of the episode shows Bart trying to keep Bob from killing him as their houseboat floats down the river to Springfield.
Cynic's Funniest Moment: NOT the rake bit, that hasn't aged well. As much as I love Homer kicking in Bart's door wielding a chainsaw wearing a hockey mask mere seconds after Bart says he's under a lot of stress, I gotta go with the part where Bob is writing all of his notes in blood and begins to write him memoirs the same way. When he starts passing out, his cellmate Snake finally tells him what we've all been thinking, "Use a PEN, Sideshow Bob!"
#9 - S09xE01: The City Of New York vs Homer Simpson
This episode was pulled from syndication after the 9/11 terrorist attacks, but since then has been put back in some regions. On a night out with the guys, resident drunk Barney Gumble draws the short straw and is the designated driver. When Homer's car hasn't been returned, The Simpsons find out that Barney went mad and drove it to New York City, a place Homer swore to never return to. While the family is off sightseeing, Homer finds his car parked in front of the World Trade Center. After failing to meet up with the man who can take the boot off of his car due to a very funny bathroom break, Homer fucking snaps and puts his car through absolute HELL to meet up with the rest of his family and leave the city.
Cynic's Funniest Moment: While I do love the running from one tower to the other to use the bathroom, I laughed hard at Homer's reaction to the Kravkalesh salesman's drink options.
Salesman: Mountain Dew or Crab Juice.
Homer: BLAUGH! UGH! EWWWWW! I'll take a Crab Juice.
#8 - S07xE03: Home Sweet Homediddly-Dum-Doodily
I think you can tell from the title which one I'm talking about. In a gross misunderstanding resulting from quite possibly the biggest clusterfuck in the history of The Simpsons, Bart, Lisa & Maggie are put in foster care under the roof of The Flanders' family. While Homer & Marge attend a parenting correctional course, Bart & Lisa become worried that Maggie is forgetting she's a Simpson (confirmed in spades in a reference to The Exorcist that is fucking creepy). Things escalate when Ned learns that the children haven't been baptized and Homer & Marge race against time to stop Ned from making their kids be Flanders' in the eyes of God, which, by the way, I think Homer shoulda beat the snot out of Ned for even ATTEMPTING such a thing, seeing as how Ned has NO right to attempt such a thing. Sure, maybe I'm looking too deep into that since it is played for laughs, but seriously, what the hell?!
Cynic's Funniest Moment: When Homer & Marge ask Grandpa Simpson about what happened and he brushes it off like a juice stain.
Homer: We leave you with the kids for three hours and the county takes them away?!
Grandpa: *walking away* Oh, bitch, BITCH, BITCH!
#7 - S06xE25 & S07XE01: Who Shot Mr. Burns?
If anyone was accusing the show of losing steam, I think this two part episode told them where to stick it. Seriously, the marketing behind this episode was great! What better way to get people to tune into the season premiere than a season finale that when the words "To Be Continued" came on screen, you literally looked up and the Gods and went "NOOOOOOOOOOOO!" On top of that, you had to wait 4 months for an answer.
An oil deposit is discovered under Springfield Elementary and the money would be used to further the school's advancements. However, his greed gets the better of him and Mr. Burns steals the oil for himself, enraging the entire town. When he sets up an instrument to block out the sun, the townspeople begin considering to take action against him. When Burns is found shot on a sundial, the entire town becomes a suspect. Homer is named the primary suspect because of an eyelash with Simpson DNA found on Burns' suit and by Burns himself, who can say only Homer's name in post-traumatic stress, despite the fact he could never remember it before. When Burns becomes coherent again, it's revealed that Maggie was the one who shot him. The ending was quite a surprise but the explanation given actually works well.
Cynic's Funniest Moment: It appears that Homer is about to strangle Mr. Burns but Burns regains his vocabulary and his old ways (i.e. not remembering Homer's name). The look on Homer's face is absolutely priceless before he lets out the most chilling, pent up, enraged "D'OH!" ever to be heard.
#6 - S08xE25: The Secret War Of Lisa Simpson
From what I remember of watching the episode syndication, you know, where they just air a marathon of Simpsons episodes as airtime filler, this episode was actually pretty rare and I took every opportunity I had to see it. On a field trip at the police station, Bart pulls a prank that blows out every glass window in Springfield. Heeding Chief Wiggum's advice, The Simpsons ship Bart off to Military School and Lisa, bored with her class, stays with him for the challenge, thinking its her dream school. Because the commanding officer (Willem Dafoe) moves all of the boys into a different hall, they immediately hate Lisa and do everything they can to try and make her quit. Bart stays by her side for support and the episode peaks with the class going across The Eliminator.
Cynic's Funniest Moment: Much like the rest of these entries, this episode was chalk full of comedic gold. However, the best is when Bart is given a grenade launcher on the firing range but intentionally misses his last target. When told of that, he quips with, "Did I?" Cut to Principal Skinner in the school parking lot covered in soot standing in front of a crater holding his keys out to unlock his now non-existent car.
Alright, two down, one to go. See in a few with entries 5-1!