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The Best ‘Simpsons’ Episodes #90-81

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On April 19, 1987, Homer, Marge, Bart, Lisa, and Maggie made their debut during a short on The Tracey Ullman Show. Two years later, Fox gave them their own program. In the three decades since, The Simpsons has become an American institution. To celebrate the 30th birthday of the greatest set of television characters of all time, let’s look back at the stories behind the 100 best Simpsons episodes.

To compile this list, I sought feedback from both hardcore Simpsons fans and former members of the show’s creative staff. Still, it was an inherently subjective undertaking. "You could choose every other episode from the first 200 episodes for your top 100 and you wouldn’t be too far off," one Simpsons writer told me. I don’t claim to be a scientician, but I tried to be meticulous. So crack open a Duff and enjoy.

Below you’ll find numbers 90 to 81 of our top-100 ranking. Click here for the entire list.


90. "Lisa’s First Word"

Season 4, Episode 10

Airdate: December 3, 1992

Written by: Jeff Martin

Another classic flashback episode, this one takes the audience back to 1983, when Marge is pregnant with Lisa and Bart has started to raise hell. "It’s not easy to juggle a pregnant wife and a troubled child," Homer says. "But somehow I managed to fit in eight hours of TV a day." After Lisa’s birth, Bart is at first skeptical of his sister. He begins to accept Lisa when she says her first word: "Bart." The story ends in the present with Maggie saying her first word: "Daddy."

Elizabeth Taylor plays Maggie. It took many takes for her to adjust her distinctively sexy voice to a level that would work for a baby. When the Hollywood icon finally nailed it, she jokingly blurted out, in Maggie’s voice, "Fuck you!"


89. "Bart Gets an F"

Season 2, Episode 1

Airdate: October 11, 1990

Written by: David M. Stern

When I was a kid, I had about half a dozen Bart Simpson T-shirts. The only one my parents didn’t allow me to wear had the word "Underachiever" stretched across it. That, whether my mom and dad liked it or not, was Bart’s identity. Still, the audience never truly sees Bart agonizing over his academics until "Bart Gets an F." When he can’t bring himself to study for his next test on colonial America, he’s forced to pray for a snow day. When his prayer is answered, he stays inside cramming while everyone else is enjoying what Mayor Quimby calls "the funnest day in the history of Springfield."

Even with the miracle, Bart fails the exam. But when his anguished offhand comment about George Washington unintentionally reveals that he actually knows the material, Mrs. Krabappel raises his score from a 59 to a 60. Bart then runs through town telling everyone he passed. "Part of this D-minus," he says to a proud Homer, "belongs to God."


88. "Boy-Scoutz ’n the Hood"

Season 5, Episode 8

Airdate: November 18, 1993

Written by: Dan McGrath

Bart unknowingly joins the Junior Campers, an organization that’s suspiciously similar to but not affiliated with the Boy Scouts of America. He’s about to quit when he learns that Junior Campers are allowed to use pocket knives. When writer Dan McGrath was young, he said, "I thought if I was grown-up enough to have a knife, that would be cool. Not that I wanted to stab anybody." Homer scoffs at Bart’s new activity, but eventually joins him on an ill-fated rafting trip that ends on a Krusty Burger on an oil rig in the middle of the ocean.

McGrath said that the classic opening scene, in which Bart and Milhouse drink an all-syrup Super Squishee and go on a Broadway-style bender, was suggested by writer and producer Mike Reiss. "Sometimes people just have a skeleton key to unlock an episode," McGrath said.


87. "A Fish Called Selma"

Season 7, Episode 19

Airdate: March 24, 1996

Written by: Jack Barth

It was about time Troy McClure got his own episode. After all, every appearance of the Hollywood caricature, whom the late Phil Hartman voiced to perfection, was a gift. In "A Fish Called Selma," the star — of TV specials (Out With Gout ’88), educational films (Designated Drivers: The Lifesaving Nerds), and movies (Dial M for Murderousness) — enters what he believes will be a career-boosting sham marriage with Marge’s sister. Another show might’ve then revealed that McClure is gay. But that’d be too predictable for The Simpsons. What he’s concealing is that he’s sexually attracted to fish. When Troy proposes having a child, Selma leaves him, choosing her pet iguana, Jub-Jub, over a husband using her to increase his fame.


86. "El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)"

Season 8, Episode 9

Airdate: January 5, 1997

Written by: Ken Keeler

First pitched by writer George Meyer early in the show’s history, then-showrunners Bill Oakley and Josh Weinstein resurrected this idea for Season 8. Meyer envisioned a story based on the psychedelic work of author Carlos Castaneda. The final product, Oakley said, was "the way he pitched it."

After eating Guatemalan insanity peppers at the chili cook-off, Homer starts hallucinating and finds himself in a brightly colored mystical world — which David Silverman animated — unlike anything ever seen on The Simpsons. In the stunning, trippy realm, he meets his spirit guide, who happens to be a coyote voiced by Johnny Cash. "It’s such a good performance," Weinstein said. The late music icon was the perfect guest star for an episode that’s truly sui generis.


85. "$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling)"

Season 5, Episode 10

Airdate: December 16, 1993

Written by: Bill Oakley and Josh Weinstein

To find quirky ideas for The Simpsons, Oakley and Weinstein used to scan USA Today’s "Across the USA" section. A blurb about riverboat gambling coming to a town in Mississippi inspired this episode, in which Mr. Burns builds a casino in Springfield.

Homer works there as a blackjack dealer and Marge becomes a gambling addict. Her absentee parenting results in Homer having to make Lisa’s geography pageant costume. The getup is supposed to resemble Florida, but she says it makes her look like a monster.

"The only monster here is the gambling monster that has enslaved your mother!" Homer says before helping save Marge. "I call him Gamblor, and it’s time to snatch your mother from his neon claws!"


84. "Treehouse of Horror IV"

Season 5, Episode 5

Airdate: October 28, 1993

Written by: Conan O’Brien, Bill Oakley, Josh Weinstein, Greg Daniels, Dan McGrath, and Bill Canterbury

The fourth Simpsons Halloween special features a spoof of "The Devil and Daniel Webster" ("The Devil and Homer Simpson"), a parody of Twilight Zone episode "Nightmare at 20,000 Feet" ("Terror at 5 1/2 feet"), and a vampire story ("Bart Simpson’s Dracula").

"The Devil and Homer Simpson" is the best of the bunch. For a single doughnut, Homer sells his soul to the Devil, who happens to be Ned Flanders. When he finishes it ("Mmm … forbidden doughnut"), Satan sends him to hell and places him in the Ironic Punishment Division. There, while he’s awaiting trial, a demon force-feeds him doughnuts until he’s about to burst. The Devil picks the jury, which is made up of, among others, John Wilkes Booth, John Dillinger, and the starting line of the 1976 Philadelphia Flyers. "That possibly was my favorite joke I’ve ever written in my life," segment cowriter Dan McGrath said.

Homer is acquitted (with a caveat) when Marge finds a wedding night photo on which Homer has pledged his soul to his wife. The picture was taken in the emergency room. "Homer ate the entire wedding cake by himself," Marge says, "before the wedding."


83. "Life on the Fast Lane"

Season 1, Episode 9

Airdate: March 18, 1990

Written by: John Swartzwelder

Of all the Simpsons characters voiced by Albert Brooks, bowling instructor Jacques may be the most underrated. When Homer gifts Marge a bowling ball with his name engraved on it — the ultimate bad birthday present — she defiantly signs up for lessons with the suave Frenchman, who charms her. As is his wont, Brooks improvised many of his lines, like this gem about Marge’s ball (and chain): "Many people have senseless attachments to heavy, clumsy things such as this Homer of yours."

Marge puts a stop to the relationship when she realizes that Homer is the love of her life. She visits him at work and the episode ends with a scene out of An Officer and a Gentleman: "I’m going to the back seat of my car, with the woman I love," Homer says, carrying Marge away, "and I won’t be back for 10 minutes!"


82. "Lisa on Ice"

Season 6, Episode 8

Airdate: November 13, 1994

Written by: Mike Scully

There had been several sports-themed Simpsons episodes during the first five seasons of the series, but never one about hockey. Writer Mike Scully, a Massachusetts native who grew up a Bruins fan, wanted to change that. "I was looking for something the show hadn’t done yet," he said. Thus "Lisa on Ice" was born.

The original idea was Bart-centric, but the focus shifted to Lisa. She’d been portrayed as competitive, but only in an academic setting. The writing staff thought it would be funny to have straight-A Lisa failing gym class, only to be told that joining a peewee team could lead to a passing grade. "You mean those leagues where parents push their kids into vicious competition to compensate for their own failed dreams of glory?" Lisa asks her PE teacher.

The audience soon learns that (a) Bart is already playing in one of those leagues and (b) Homer is the kind of damagingly overzealous sports dad who began making the news in the ’90s. "Marge, Bart rides up in the front seat today because he’s a good guy at sports," he says after his wife tells Lisa that it’s OK that she’s not good at sports. After his hockey game, Bart grabs his stick and shoots garbage at Lisa, who parries it away. Apu notices her excellent reflexes and recruits her to play goalie for his team. It was a natural position for her. "Being tortured by Bart," Scully said, "she was constantly deflecting things away from her."

Bart and Lisa spend the rest of the episode as intense rivals. "Hack the bone!" Lisa tells her teammates while in net. That’s a tribute to Islanders goalie Billy Smith, whom Scully used to watch when the 1982 Vezina winner was a minor leaguer in the writer’s hometown. "Anybody who skated into his crease was gonna get a stick across the ankles," Scully said.

In the final scene, Lisa’s and Bart’s teams square off. The tie game comes down to a penalty shot, but before the latter attempts to score on the former, the siblings’ relationship flashes before their eyes. At that moment, they drop their equipment and embrace. The crowd then starts a riot, proving the number-one rule of youth sports: adults ruin everything.


81. "22 Short Films About Springfield"

Season 7, Episode 21

Airdate: April 14, 1996

Written by: Richard Appel, David S. Cohen, Jonathan Collier, Jennifer Crittenden, Greg Daniels, Brent Forrester, Rachel Pulido, Steve Tompkins, Bill Oakley, Josh Weinstein, and Matt Groening

If an episode made up of a bunch of mostly unrelated vignettes sounds overly ambitious, that’s because it is. Thankfully co-showrunners Oakley and Weinstein went ahead with the project anyway. "We didn’t have to answer to anybody," Oakley said. "That was the only way that [idea] got through."

The episode "The Front" had included a short segment called "The Adventures of Ned Flanders." Oakley and Weinstein figured it’d be fun to showcase other minor characters. Pulp Fiction had also recently been released and the pair wanted to try non-linear storytelling. To decide assignments, the writers picked character names out of a hat.

Among others, there are stories about Bumblebee Man, Cletus the Slack-Jawed Yokel, and Nelson. Oakley drew Superintendent Chalmers and wrote the most memorable scene in the episode. Principal Skinner attempts to cook his boss dinner, burns the roast, and then serves Krusty Burgers, which the principal famously calls "steamed hams."

"That’s gonna be on my tombstone," Oakley said.

Click here for episodes 80 to 71.

Return to The Ringer’s 100 Best ‘Simpsons’ Episodes.

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