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The Best ‘Simpsons’ Episodes #30-21

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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 30 to 21 of our top-100 ranking. Click here for the entire list.


30. "Simpsons Roasting on an Open Fire"

Season 1, Episode 1

Airdate: December 17, 1989

Written by: Mimi Pond

Although not planned as the series premiere (the intended debut episode was still in production in late 1989), "Simpsons Roasting on an Open Fire" was an irreverent and heartfelt introduction to America’s favorite animated family. The uniquely syrup-free (at least for the time) Christmas special focuses on holiday anxiety and the wiseassery of Bart, who gets a tattoo. Its removal costs the family its Christmas funds and forces Homer to work as a mall Santa.

"I hate Christmas," said writer Mimi Pond, whose favorite moments include Homer’s quest to find his kids "pathetic presents" at the Circus of Values and Lisa repeatedly writing a single phrase — "A PONY" — on her Christmas list. In the climactic scene at the dog track, a desperate Homer bets on a 99-to-1 shot named Santa’s Little Helper. The pooch finishes last, Homer loses his money, but the Simpsons adopt the unwanted greyhound. That kind of bittersweet ending became a Simpsons trademark.


29. "Separate Vocations"

Season 3, Episode 18

Airdate: February 27, 1992

Written by: George Meyer

In "Separate Vocations," The Simpsons cleverly flips the script. When the results of the Career Aptitude Normalizing Test (yes, the CANT) reveal that Bart would be suited for law enforcement and Lisa for homemaking, the two immediately begin conforming to new expectations. Feeling that their futures are now set, the former evolves into a fascistic authority figure while the latter devolves into a wiseass delinquent.

It’s amusingly jarring to watch two iconic characters, who by then were already well-defined, switch roles. Empowered by going on a police ride-along, Bart becomes a hall monitor and teams up with Principal Skinner to fight crime at Springfield Elementary. After the school psychologist tells Lisa about her "scientifically selected career," she desperately heads to a music academy for evaluation. The teacher is impressed with her saxophone playing, but claims that her stubby fingers will prevent her from becoming a professional. Upset, she falls in with the wrong crowd. After Miss Hoover punishes her for insolence — "Well, you’re earning your 18 grand a year," she says after her answer key–equipped teacher can’t even come up with the correct response to a question about Andrew Jackson — Lisa steals each member of the faculty’s teacher’s edition textbook.

Bart investigates and quickly figures out that Lisa is the culprit. Shocked by her actions, he takes the blame. When she asks why, he replies, "Because I didn’t want you to wreck your life. You got the brains and the talent to go as far as you want. And when you do, I’ll be right there to borrow money." Nancy Cartwright, who voices Bart, won an Emmy for the performance.

While the episode obviously argues that fate isn’t predetermined, it also makes the case for self-awareness. For Bart, that means realizing that deep down he’s someone who starts rebellions, not crushes them.


28. "Homer’s Phobia"

Season 8, Episode 15

Airdate: February 16, 1997

Written by: Ron Hauge

"To have a gay character on television today is nothing," John Waters said recently. But in 1997, when the transgressive filmmaker appeared on an animated series as a gay man named John, it was a pretty big deal. (A censor at Fox at first deemed the episode unsuitable for air.) The Simpsons handled the guest spot cleverly, choosing to call out Homer’s homophobia without sermonizing.

In the episode, Homer panics at the mere possibility of his son being gay. As John introduces aspects of gay culture to the mostly unfazed Simpsons, Homer attempts to set Bart straight. After a visit to the gay steel mill–dance club — a classic scene conceived by writer Steve Tompkins — and a failed hunting trip that ends with John saving the day, Homer at least starts to shake his bigotry. And to the show’s credit, Waters’s character doesn’t let Homer off the hook.

"Well, Homer, I won your respect, and all I had to do was save your life," he says as the episode comes to a close. "Now, if every gay man could just do the same, you’d be set."


27. "A Milhouse Divided"

Season 8, Episode 6

Airdate: December 1, 1996

Written by: Steve Tompkins

All sitcom couples, including Homer and Marge, fight. But they rarely break up. In this episode, The Simpsons actually rips off the Band-Aid. During a dinner party, Milhouse’s parents Kirk and Luann clash. Then the latter demands a divorce.

To its credit, "A Milhouse Divided" is unbelievably sad. Kirk might be one of the most pathetic characters in TV history. He loses his job at the Southern Cracker factory and lives in the Bachelor Arms apartments, where he has a race car bed. (The first draft of the script featured a divorced mortician neighbor, but he got cut.) As writer Steve Tompkins put it: this wasn’t American Beauty’s Lester Burnham smoking weed and lifting weights. Sometimes after a divorce, Tompkins said, "You go back to a sort of arrested adolescence."

"I sleep in a racing car," Kirk tells Homer, trying to appear proud. "Do you?" Homer’s flat response is unintentionally brutal: "I sleep in a big bed with my wife."

Meanwhile, Milhouse gets support from two children of divorce: Nelson and Kearney. Tompkins enjoyed having the two bullies show some sympathy for a change. A liberated Luann also starts dating again. On the other hand, a despondent Kirk reacts to the split by cutting a single called "Can I Borrow a Feeling?" The writers borrowed the title from an obscure record by singer Cody Matherson that they’d discovered on the internet. It’s called "Can I Borrow Another Feelin’?" The cover art is a masterpiece.

The breakup causes Homer to question his devotion to his wife. To make up for their shotgun first wedding, Homer files for divorce and stages a second wedding. "I didn’t want a hokey second wedding like those ones on TV," Homer says, "this one is for real." (Adding that line made Tompkins feel much better about indulging in the cheesy trope.) At the party, Kirk gets on the mic and sings his song to Luann. She rebuffs him, erasing any hope of a reconciliation.


26. "Homer Badman"

Season 6, Episode 9

Airdate: November 27, 1994

Written by: Greg Daniels

"Homer Badman," which Greg Daniels named so simply as a goof on the clever titles his fellow writers sweated over for hours, nailed both ’90s tabloid culture and correctly envisioned today’s noxious media climate. "Clearly," Daniels said, "the show was powerless to change anything there."

But instead of the meat of the episode, let’s start with its sweet opening set piece: the Candy Convention, where Homer drags Marge so that she can stuff her bulging coat with goodies. While rampaging through the trade show — Says Homer: "I feel like a kid in some kind of a store" — he comes upon a gummy Venus de Milo. ("I’m a huge gummy fan," Daniels said.) Homer steals the priceless confection and escapes with Marge by tossing a grenade made of Pop Rocks and Buzz Cola and sprinting away as it explodes behind them. (The trend at the time, Daniels said, was action heroes "running away from fireballs.")

When Homer drops off babysitter Ashley that night, he notices that she’s sat on the gummy Venus. Unwisely, he reaches out to grab it off the back of her pants. The next morning, the graduate student, who the audience learns had spoken to Lisa’s class about gender equality, accuses Homer of sexual harassment. Protesters hound him, shouting chants that Marge admits are "very catchy and memorable." Sleazy tabloid program Rock Bottom then edits an interview with Homer to make him look like a predator.

Before the internet and TV joined forces to form a hysterical two-headed media monster, The Simpsons showed how the endless news cycle can tear someone to shreds. Homer is so shaken that at one point he dreams of starting a new life … under the sea. "There’ll be no accusations," he memorably sings to himself, "just friendly crustaceans." The public doesn’t grant absolution until Groundskeeper Willie produces voyeuristic footage proving that Homer didn’t grope the babysitter. But by then, Dennis Franz has already played him in a television movie called Homer S.: Portrait of an Ass-Grabber.

Two decades after it first aired, "Homer Badman" still means a great deal to Daniels. He said that Ricky Gervais’s fondness for the episode helped Daniels land the gig to adapt The Office for American TV.


25. "Homer Goes to College"

Season 5, Episode 3

Airdate: October 14, 1993

Written by: Conan O’Brien

When work requires Homer to take a nuclear physics class at Springfield University, he acts exactly as you’d expect: like a man whose only previous exposure to college was Animal House. He spends his time pulling pranks like stealing rival Springfield A&M’s mascot Sir Oinks-a-Lot. That stunt results in the dean expelling his three nerdy friends. (As they’re walking off campus, criminal Snake robs them by claiming that he’s the Wallet Inspector.)

After the three pals overstay their welcome at the Simpsons’ house — they tie up the family’s phone lines with dial-up internet — Homer helps them get back into school. They then help him study for his final, which he fails anyway. Homer only passes because the nerds hack into the school’s grading system and give him an A+.

The episode’s best joke — and one of the most memorable in the entire series — was an accident. At one point, Homer accidentally lights the house on fire and sings, "I am so smart, I am so smart, S-M-R-T, I mean S-M-A-R-T." Dan Castellaneta wasn’t supposed to misspell the word, but the mistake was too funny to cut.


24. "Lisa the Greek"

Season 3, Episode 14

Airdate: January 23, 1992

Written by: Jay Kogen and Wallace Wolodarsky

"Well, I like the 49ers because they’re pure of heart, Seattle because they’ve got something to prove, and the Raiders because they always cheat." — Lisa the sharp

In this ode to both father-daughter bonding and gambling on the NFL, Homer discovers that Lisa can pick winners. In an attempt to bond with her uninterested dad, she asks to watch the game with him. He reluctantly says yes, forcing her to sit at the end of the couch. Later that afternoon, Homer desperately asks Lisa who she thinks will win the Miami-Cincinnati matchup. She goes with the Dolphins, Homer puts $50 on them, and he cashes in. When Lisa asks her dad why he needs to make "the savage ballet of football" even more exciting by risking money on it, he responds with my favorite explanation of sports betting of all time:

"You like ice cream, don’t you?" he asks Lisa, who says yes. "Don’t you like ice cream better when it’s covered with hot fudge and mounds of whipped cream, chopped nuts, and those crumbled-up cookie things they mash up? Mmm … crumbled up cookie things."

And so every Sunday from then on is Daddy-Daughter Day. Lisa embraces their new ritual until she correctly suspects that Homer’s just using her. (With his winnings, Homer is able to buy Lisa the entire line of Malibu Stacy accessories, Bart a PG-13-rated swearing machine, and Marge a bottle of Meryl Streep’s Versatility.) Before the Super Bowl, a disappointed Lisa issues her prediction to Homer: "If I still love you, Washington. If I don’t, Buffalo." Homer makes no money on the Skins’ victory — Moe refuses to take his bets — but wins back his daughter’s love. Realizing there’s more to his relationship with his older daughter than football, Homer soon accompanies her on a hike of Mount Springfield.


23. "Homer’s Enemy"

Season 8, Episode 23

Airdate: May 4, 1997

Written by: John Swartzwelder

The bleakest installment of The Simpsons ever, "Homer’s Enemy" shows the world what it would be like to interact with Homer Simpson in the real world. Hank Azaria brilliantly voices Frank Grimes, a self-made nuclear plant employee who can’t take his coworker’s laziness. The character looks like Michael Douglas in Falling Down but the uncommonly versatile Azaria modeled him after William H. Macy.

Grimes spends the entire episode (rightfully) grumbling about Homer and finally gives in to his rage. In a fit of mock ineptitude, he runs around the plant pretending to be Homer. He sees a sign that reads "Extremely High Voltage," says, "Well, I don’t need safety gloves, because I’m Homer Simp — " and then grabs exposed wires. Before he can even finish Homer’s last name, Grimes is electrocuted. Homer proceeds to sleep through the funeral. Even in death, the proudly competent Grimes gains no respect.

The episode is polarizing — some fans find the tone unsettling and just plain mean — but revealing. "Grimes’s cardinal sin was that he shined a light on Springfield," Simpsons writer George Meyer told The Believer in 2004. "He pointed out everything that was wrongheaded and idiotic about that world. And the people who do that tend to become martyrs. He said things that needed to be said, but once they were said, we needed to destroy that person."


22. "Secrets of a Successful Marriage"

Season 5, Episode 22

Airdate: May 19, 1994

Written by: Greg Daniels

When writing "Secrets of a Successful Marriage," Greg Daniels asked himself a question: "Is there anything Homer is good at?" The answer, he said, was that "his relationship with Marge was good." But, Daniels added, "the act of examining it started to screw it up."

In the episode, Homer teaches an adult education class about marriage. Without any academic credentials to fall back on, he resorts to telling his students secrets about his own marriage. Marge warns him against doing that, he ignores her, and then she kicks him out of the house. To that point, they’d never had a bigger fight. What makes the episode so moving is that the couple doesn’t immediately reconcile.

Devastated, Homer camps out in Bart’s treehouse and prunes a plant so that it looks like Marge. As usual, he’s saved by Lisa’s wisdom. "To get mom back," she says, "you just have to remember what you give her that nobody else can." That turns out to be, as Homer tells a soon-to-relent Marge, "complete and utter dependence!"


21. "Rosebud"

Season 5, Episode 4

Airdate: October 21, 1993

Written by: John Swartzwelder

Mr. Burns as Charles Foster Kane, a tiny stuffed bear named Bobo, and the Ramones combine to form an episode that’s as satisfying as 64 slices of American cheese. Early on, Springfield’s Scrooge laments the loss of his childhood teddy. Not even the sound of a legendary punk band serenading him at his birthday party can cheer him up. "It took us longer to figure out how to play ‘Happy Birthday’ than it did to record it," Johnny Ramone told Goldmine magazine in 1994. "It became difficult to play because you only hear it a capella." At the end of the song, Burns tells Smithers to "have the Rolling Stones killed."

Bobo, as it turns out, has traveled around the world for half a century before ending up in a bag of ice at the Kwik-E-Mart. Bart finds Bobo and gives it to Maggie. After realizing what they have in their possession, the Simpsons plan on selling it back to Burns. However, the baby refuses to let go of the bear. Burns tries just about everything to get it back — even taking over every TV station doesn’t sway a tortured Homer — before giving up. Out of pity for the old man, Maggie then hands over Bobo. It’s the only time in Simpsons history where Burns is truly happy. "Well, we didn’t get any money, but Mr. Burns got what he wanted," Homer says. "Marge, I’m confused! Is this a happy ending or a sad ending?"

For the eternally underappreciated Ramones, who were big Simpsons fans, the appearance was validation. "I thought it was like one of the ultimate honors," Joey Ramone told Goldmine. "because [Matt Groening’s] a fuckin’ genius and the show’s great. I think it’s the best show on television."

Click here for episodes 20 to 11.

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