Season 8 was the second and final season ran by Bill Oakley and Josh Weinstein. Like Season 7, this season has several specific episodes the two wanted to do like an Itchy & Scratchy episode, a Sideshow Bob episode, a format-bending episode (the Spin-Off showcase), and though there were a few episodes focused on side characters there were still plenty of episoded focused on the relationships within the family.
Its odd that I found this season's Treehouse of Horror to be the least funniest of all 25 episodes, but then again this entire season was so consistently good there was no choice but to have one of these fine episodes be considered 'the worst'. For many, Season 8 is considered the final season of the Simpsons' supposed golden age, and if that were the case, then the golden age ends on a superb note.
Season 8 Overall Score: 9.25
Favorite Season 8 Episode: The Springfield Files
Least Favorite Season 8 Episode: Treehouse of Horror VII
01) Treehouse of Horror VII
The Thing and I: Bart learns he has an evil twin, the deranged Hugo.
The Genesis Tub: Lisa accidentally creates life, which Bart makes enemies of.
Citizen Kang: Kang & Kodos replace Bob Dole & Bill Clinton so that one of them can conquer Earth.
02) You Only Move Twice
Homer moves the family to Cyprus Creek to work for Globex Corporation, where his new boss, Hank Scorpio, is a wonderful person who, unknown to Homer, is actually a supervillain.
03) The Homer They Fall
Learning that Homer can take punches to the face very well, Moe gets Homer involving in the boxing circuit.
04) Burns, Baby Burns
Mr. Burns learns he has a son: a rather oafish comedian of a son voiced by Rodney Dangerfield that he soon learns to dislike.
05) Bart After Dark
With Marge away, Homer forces Bart to do house chores for an old woman after Bart accidentally destroys a gargoyle at her house. Bart then learns that the house is actually a burlesque house.
06) A Milhouse Divided
After the Van Houtens decide to split up during Marge's dinner party, Kirk's situation really makes Homer think, and Homer ends up making a difficult choice.
07) Lisa's Date with Density
Lisa inexplicably gains a crush on Nelson Muntz, and dates him in the hopes of changing him for the better. Meanwhile, Homer finds an auto-dialer and quickly starts a telemarketing scheme.
08) Hurricane Neddy
After a series of disasterous events finally causes Ned Flanders to lose his cool, its revealed that he gained said cool after a long spanking program which leaves Ned needing to learn how to control his anger.
09) El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)
Homer ingests some insanity peppers at a chili cookoff, going to a 'strange fantasy world', learning he needs to find his soulmate.
10) The Springfield Files
In a tale partially narrated by Leonard Nimoy, Homer encounters what appears to be an alien, but when mostly nobody believes him, he goes out to get proof.
11) The Twisted World of Marge Simpson
Marge is kicked out of an investing group for not being risky enough, and gets back at them by investing in a risky pretzel business.
12) Mountain of Madness
Mr. Burns take his workers up to a snowy mountain for a teamwork exercise. He and Homer are paired up, and reach the cabin first, but then undergo a true test of teamwork.
With Marge losing her hair from stress, the family decides to hire a nanny. A rather whimsical woman applies for the job, but finds she got more than she bargained for.
14) The Itchy & Scratchy & Poochie Show
Fearing the show has gotten stale, Roger Meyers Jr. adds a new character, voiced by Homer, called Poochie, however Poochie is too extreme to be liked.
15) Homer's Phobia
Homer comes across a guy he later learns is gay, and becomes afraid that Bart could 'catch' it and become gay as well, going through efforts to prevent that outcome.
16) Brother from Another Series
Sideshow Bob, a reformed man, gets out on a work program thanks to his once-estranged brother, Cecil. Bart, however, is highly suspicious of the whole thing.
17) My Sister, My Sitter
Lisa takes up babysitting and is praised across town for it. However, she is tasked with babysitting the most difficult kid to babysit around: Bart Simpson.
18) Homer vs. the Eighteenth Amendment
After a crazy St. Patrick's Day, its learned that the town enacted a prohibition law 200 years ago. With Rex Banner overseeing the law, Homer takes matters into his own hands.
19) Grade School Confidential
Principal Skinner and Mrs. Krabappel fall in love, a fact only Bart knows at first. Knowing what could happen if everyone found out, the two make a deal with Bart to keep silent.
20) The Canine Mutiny
Having acquired a fake credit card, Bart buys among other things an outstanding dog. When the repo men eventually come to reclaim everything, Bart gives up his other dog, Santa's Little Helper.
21) The Old Man and the Lisa
Poor investment decisions leave Mr. Burns broke. He turns to Lisa, who previously chided him for not even knowing about recycling, for help. She agrees to help, but only if Burns does so honestly.
22) In Marge We Trust
Marge takes over the lethargic Reverend Lovejoy's job of giving advice to others. Meanwhile, Homer finds a strange Japanese box featuring his face.
23) Homer's Enemy
Frank Grimes, a man who has worked hard to get to where he's at, meets Homer Simpson. The two do not get along very well.
24) The Simpsons Spin-Off Showcase
Featuring 'spin-offs' for characters like Chief Wiggum, Moe, and even (most of) the Simpson family itself.
25) The Secret War of Lisa Simpson
Bart's latest prank gets him in so much trouble, he's sent to military school. Lisa is facing so little challenge from school, she decides to enroll in military school.