Episodes:

Lard of the Dance

Homer’s wacky job of the week is grease collection and sales.  A subplot involving guest star Lisa Kudrow, about the pressure on young kids to act like grownups is far more interesting.

The Wizard of Evergreen Terrace

Homer realizes that at thirty-eight, he has yet to accomplish anything meaningful (Besides, you know, going into space). He becomes obsessed with Thomas Edison and we are treated to another “Homer gets a wacky job” episode.

Bart the Mother

One of the highlights of this season.  Bart accidentally kills a mother bird and tries to raise her eggs as his own.  This episode manages to be touching, slightly cynical and genuinely surprising.  Bart the Mother also marks Phil Hartman’s final performance.

Treehouse of Horror IX

Hell Toupée:  A riff on the Jeff Fahey classic Body Parts.  Homer gets a hair transplant from Snake, which turns out to be evil.  One of the weakest Treehouse segments.

The Terror of Tiny Toon:  Bart and Lisa are sucked into the Cartoon-within-a-cartoon world of Itchy and Scratchy.  A fun, but relatively forgettable entry.

Starship Poopers:  Maggie’s real father turns out to be Kang.  The strongest of these three; a lame Jerry Springer parody is offset by Kang’s freaking hilarious insemination method.

When You Dish Upon a Star

Homer becomes private assistant to Kim Basinger, Alec Baldwin and Ron Howard.  This episode manages to combine Homer getting a wacky job with gratuitous celebrity cameos in an episode that personifies what was starting to go wrong with the series.

D'oh-in' in the Wind  

When Homer sets out to find out what his middle initial stands for, he finds the commune his mother used to belong to, now a Ben and Jerry’s style juice plant run by George Carlin and Martin Mull.  Despite the fact that hippy jokes are a bit over-played, this is another of the season’s best episodes.

Lisa Gets an A

Lisa cheats on a test and gets an A.  This puts the schools average GPA above the state-wide minimum standard and results in the school receiving basic financial assistance.  This episode also features Homer’s relationship with Mister Pinchy the lobster.  Another very strong episode, with an ending that is as upsetting as it is funny.

Homer Simpson in: "Kidney Trouble"

When Homer accidentally causes Grandpa’s kidneys to explode, he offers to donate his own, then chickens out.  Touching and uncomfortable, this is one of the best Grandpa-centric ones.  Oh man, three great episodes in a row… That means it must be time for…

Mayored to the Mob

...  Homer in a wacky job and a strained celebrity appearance!  This time he rescues Mayor Quimby and Mark Hamill from a riot at the Springfield Bi-Mon-Sci-Fi-Con and becomes the Mayor’s new bodyguard.  Despite the fact that it is nearly impossible for me to watch most pre-prequel Star Wars humor, Quimby does get some very funny bits.

Viva Ned Flanders

When it is revealed that Ned Flanders is actually sixty years old he realizes that, while it has left him looking fabulously young, he has not actually lived his life to the fullest.  He asks Homer to share his lust for life with him, which results in a trip to Vegas and two new cocktail waitress wives.  While there are some decent gags here, it is one of the weaker Flanders based episodes.

Wild Barts Can't Be Broken

When Homer, Lenny, Carl and Barny get drunk and trash the elementary school, Wiggum blames it on “punk kids” and imposes a curfew.  Inspired by a Village of the Damned style film called The Bloodening, the kids of Springfield start up a pirate radio station and use the town’s hidden sins to blackmail the adults.  Not quite as wacky as that description makes it sound, this is an episode that feels more like a collection of obligatory Simpsons gags than a cohesive whole.  Plus, for some reason, the kids’ fake English accents scrape my nerves.

Sunday, Cruddy Sunday

(Man, I never realized how terrible some of these episode titles are)

A Superbowl extravaganza featuring the voices of Fred Willard, Dolly Parton, Rupert Murdoch and a bunch of football players.  Pro athletes are rarely the best (correction:  even mildly viable as) voice actors and this is no exception.  Fortunately, Dan Marino’s flat delivery is offset by Fred Willard reprising his roll as That-Character-That-Fred- Willard-Always-Plays-That-I-Really-Should-Be- Sick-Of-But-For-Some-Reason-I’m-Not.

Homer to the Max

The hit TV show Police Cops introduces a bumbling doofus named Homer Simpson, prompting Homer to change his name to Max Power.  Though you could argue that this is another Homer gets a wacky profession episode at heart, it is still one of my favorites.

I'm With Cupid

Apu, in an attempt to make up for neglecting Manjula, plans a series of increasingly outlandish Valentines gestures, making the rest of the men in town look bad.  I have always enjoyed episodes where Apu takes the spotlight.  One of the strengths of The Simpsons has been the way that they can take a one note stereotype joke, like the foreign 7-11 clerk, and turn it into something both deeper and funnier.

Marge Simpson in: "Screaming Yellow Honkers"

Marge to become intoxicated and enraged by the raw power of the Canyonero SUV, landing her in traffic school for road rage.  Though more relevant when it premiered in 1999, this is still one of better social satire episodes on a show that was full of great ones.

Make Room for Lisa

Homer allows a cell phone tower to be installed in Lisa’s bedroom, forcing her to move in with Bart, while Marge becomes obsessed with using the tower to eavesdrop on the neighbors.  Another episode that feels more like a collection of obligatory Simpsons bits than a strong narrative.

Maximum Homerdrive

Homer challenges a truck driver to a steak eating contest, which leads to the man’s death and Homer’s job of the week.  Still, this episode is totally worth it for The Slaughterhouse restaurant and Señor Ding-Dong.

Simpsons Bible Stories 

Bible stories with the Simpsons in the lead rolls.  This is my least favorite of the episodes in which they cast the residents of Springfield as literary/mythological characters.  Considering that, in earlier seasons, the show had some of the most thoughtfully edgy religious humor on television, this one feels surprisingly toothless.  It gets half-credit for adding a talking pig to the Garden of Eden, but really that’s just my fetish.

Mom and Pop Art

Homer’s attempt at building a backyard BBQ pit lands him a… wait for it… new and unlikely job!  This time it’s as a pop artist.  There are a few fun jabs at the art world in the episode, but come on.  Every comedy show in history has done an episode that makes fun of snooty art types, including earlier seasons of The Simpsons.  Also, in the wake of Hurricane Katrina, the ending (Spoiler: Homer floods Springfield) is kind of unintentionally creepy.

The Old Man and the "C" Student   

When Bart’s edgy standup act causes Springfield to lose the Olympic Games, he is forced to work at the Springfield Retirement Castle, where he attempts to wake up the seniors and teach them to savor life.  Another of the strongest episodes of the season; The Simpsons has always been great about addressing/mocking the way that out culture treats the elderly.  Extra points awarded for a bit of physical comedy featuring Lenny with a spring in his eye.

Monty Can't Buy Me Love  

Jealous of Richard Branson style hip-billionaire Arthur Fortune, Mister Burns takes Willy, Frink and Homer, then sets out to capture the Loch Ness Monster and win the hearts of America.  Okay, this episode actually is as weird as the description makes it sound.

They Saved Lisa's Brain

Lisa is invited to join the Springfield chapter of MENSA.  When Quimby skips town, they are left in charge and set out to usher in a new age of enlightenment.  Unfortunately, this is hampered by the fact that even geniuses can be selfish and socially inept.  Stephen Hawking guest stars in one of the most gratuitous-feeling celebrity appearances to date.  But, really, who cares?  It’s Stephen Hawking!

Thirty Minutes Over Tokyo

The Simpsons go to Japan.  I am going to go ahead and give this one the benefit of the doubt and assume that making fun of Japanese junk culture and game shows felt fresher in 1999 it does do now. 

Audio/Video/Extras

As with all of the Simpsons releases, this set is chock-full of extras.  You get commentary on every episode, deleted scenes, artwork, Butterfinger commercials, animation tests, a couple of featurettes and a friendly welcome from Matt Groening.

As this review is of a screener copy I can’t attest to the audio or video quality, except to say, it’s The Simpsons.

Final Words

Even here, at the beginning of it’s downward spiral, The Simpsons still qualifies as one of the funniest most insightful shows in the history of television.