I haven't mentioned the word "showrunner" in these season recaps yet, but I will starting with this one. Matt Groening, James L. Brooks and Sam Simon ran the show for the first two seasons and are still executive producers to this day. Seasons 3 and 4, considered by most to be an improvement over the first two, were co-ran by Al Jean & Mike Reiss. As Jean & Reiss left to start work on The Critic, Season 5 was the first season ran by David Mirkin (with Jean/Reiss in charge of a couple of episodes here and there). The phrase and the people in that position for this show will become important several seasons from now.
As for Season 5 itself, its a very solid season overall, a step down from the high-quality Season 4 but still a very good season overall with nothing you could really call a "dud" for an episode. There is more of a focus on the secondary characters of the series - because you can really only do so much with the main cast - and so we've got episodes focused on people like Apu, Principal Skinner, a couple with Mr. Burns, and even Marge's mother. It makes for a varied season, with several superb episodes, and a couple that are "merely" above-average.
Season 5 Overall Score: 9.05
Favorite Season 5 Episode: Cape Feare
Least Favorite Season 5 Episode: Secrets of a Successful Marriage
01) Homer's Barbershop Quartet
Homer tells the kids about the time he, Skinner, Apu and eventually Barney were a famous barbershop group.
02) Cape Feare
Sideshow Bob attempts to kill Bart for foiling his previous schemes. The Simpsons enter the Witness Relocation Program to escape, but Bob follows them regardless.
03) Homer Goes to College
Needing to pass a nuclear physics course to keep his job, Homer is admitted into Springfield University, where he intends to party down instead of actually study.
Mr. Burns yearns for his long lost childhood bear, which through an odd series of events is now in the hands of Maggie Simpson.
05) Treehouse of Horror IV
The Devil and Homer Simpsons: Homer sells his soul for a donut.
Terror at 5 1/2 Feet: Bart is the only one who sees a gremlin tearing apart the school bus.
Bart Simpson's Dracula: Mr. Burns is a vampire, and he's able to convert Bart into one as well.
06) Marge on the Lam
Marge befriends Ruth Powers, and the two go out on the town, which Homer doesn't like. Then we learn Ruth's car is stolen!
07) Bart's Inner Child
The town listens to a supposed self-help guru to follow their inner-child, using Bart of all people as the example they should follow.
08) Boy-Scoutz 'n the Hood
After an immense sugar high, Bart is shocked to learn he joined the junior campers. He decides to stay on, much to Homer's amusement.
09) The Last Temptation of Homer
Homer becomes attracted to a new coworker who is basically a female version of him. Meanwhile, Bart is given a series of medical treatments which leave him looking like a nerd.
Mr. Burns builds a casino to boost Springfield's economy. Among its most frequent patrons... Marge Simpson?
11) Homer the Vigilante
When a cat burglar's robbery spree claims Lisa's saxophone, Homer leads a vigilante group to get it back, while running their own brand of justice of course.
12) Bart Gets Famous
Becoming Krusty's assistant, Bart is asked to fill in for a sketch, where his blunder creates the biggest catchphrase of that month.
13) Homer and Apu
Apu gives Homer food poisoning a bunch of times. Homer exposes Apu to the news. Apu gets fired and decides to work for Homer to make up for poisoning him. Its the epic of the ages.
14) Lisa vs. Malibu Stacy
Upset that a new talking doll spouts out demeaning things to women, Lisa begins an effort to sell a doll that'll be a positive role model for young girls. Good luck with that.
15) Deep Space Homer
Homer is chosen by NASA as their first average Joe astronaut, in a desperate attempt to gain TV ratings.
16) Homer Loves Flanders
After Ned takes Homer to the big football game, Homer becomes friends with him. The new friendship quickly wears out Ned and his family.
17) Bart Gets an Elephant
After winning a radio contest, Bart insists he receive its gag prize: an African elephant. So, that's what he gets.
18) Burns' Heir
Mr. Burns realizes his fortune is currently heir-less and decides to give it all to Bart, while at the same time trying to groom him into the next Mr. Burns.
19) Sweet Seymour Skinner's Baadasssss Song
100th Episode: Skinner is fired after failing to contain Bart's dog properly. Feeling bad for what happened, Bart befriends Skinner afterward.
20) The Boy Who Knew Too Much
Bart skips school, allowing him to witness a supposed beatdown between Freddy Quimby and a waiter. Knowing Quimby is innocent, Bart decides whether to stay silent or testify, revealing to juror Skinner that he skipped school.
21) Lady Bouvier's Lover
Marge tries to hook up Abe Simpson with her mother, both lonely seniors, but Mr. Burns takes an interest in the elder Bouvier as well.
22) Secrets of a Successful Marriage
Homer teaches an adult education course on marriage, but can only keep the class interested by telling them stories about him and mostly Marge. That'll end well.