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D’oh! ‘The Simpsons’ Turns 25: A Look at the Golden Years

The first episode of “The Simpsons” aired 25 years ago today. Here’s a fan-fueled look at the golden years of TV’s longest-running sitcom.

Hi! I’m Laurie Ulster. You might remember me from such Bio articles as, “The Love Boat: Where Are They Now?” and “A Star Trek Nerd Goes To Comic-Con.”

Today, I’m here to talk to you about America’s longest-running sitcom of all time, The Simpsons. What started as a series of crude but catchy shorts on The Tracey Ullman Show in 1987 is now in its 26th season, permanently embedded in our collective pop culture consciousness. Don’t believe me? Go look up “d’oh” in the dictionary, and then come back with your tail between your legs because yes, it’s in there. Don’t have a tail? No problem! Just read my next article, “Our Vestigial Tails: Where Did They Go?”  

What is that makes The Simpsons endure? It starts with brilliantly created characters, who we completely believe in, animation be damned. The show is densely layered, with its humor coming from wacky storylines, smart cameos, slapstick, and references both obvious and esoteric. (Did you ever notice that Sideshow Bob’s prison number is sometimes the same as Les Miserables’ Jean Valjean’s?) The writers and animators have always been masters of detail, injecting jokes and sight gags into every scene. 

Everyone has a favorite scene, episode, season, catch phrase, side character, and member of the Simpson family, and the only way to hit them all is to watch the entire series from start to finish. In lieu of that, we’re going to hone in on what we think are the golden years of the show, its creative heyday, so to speak. There’s no better way to explain what makes those seasons solid gold than to give you a virtual feast of Simpsons clips to walk through. Sit back, relax, and enjoy the ride, as we highlight in clips and photos of what made The Simpsons so darned great from season two to season ten. 

SEASON TWO

Lisa fell in love with her substitute teacher (Dustin Hoffman), called Homer a baboon, and experienced her first heartbreak, all in one episode. 


Lisa: “Places where my intelligence will be an asset and not a liability?”


Mr. Bergstrom: “Yes, there is such a place. Believe me, it’s true.” 
Lisa: “I believe everything you say.” 

Lisa and her substitute teacher crush. 

Homer met his long-lost brother Herb (Danny DeVito), a rich tycoon car manufacturer. Herb bravely gave Homer free rein to design a car for the average man:

And … that was the end of Herb’s company. 

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Homer’s very Homer car design.

And season two brought us Harvey Fierstein as Karl, whose mother told him never to kiss a fool. When Homer found the miracle hair product he’d been dreaming of, he briefly became a junior executive at the nuclear power plant, and got himself an assistant.

It also gave us the return of Bart’s nemesis, Sideshow Bob (Kelsey Grammer). His declarations of love for aunt Selma fooled everyone but Bart, who knew that Bob had to have a diabolical plan in the works. He had a hard time explaining it to Homer, though.

And who could forget this one? “Mom it’s broken, Mom it’s broken …” from “Bart vs. Thanksgiving.” It’s a very sweet and funny episode, proving that despite the wackiness that abounded, The Simpsons always has a heart. 


SEASON THREE

Homer’s brother Herb came back to rebuild his fortune, and built a baby translator with some help from Maggie. Nothing beat hearing Danny DeVito’s low, husky voice interpreting for baby Maggie, “Lavish attention on me, and entertain me.” “I have soiled myself. How embarrassing.”

Homer’s shining moment with the nuclear power plant’s baseball team was usurped by ringers Darryl Strawberry, Roger Clemens, Wade Boggs, José Canseco, and more. Don Mattingly really wanted to play, too:


Bart fell down a well – after PRETENDING to fall down a well – and Sting headed up a group of celebrities in a benefit song (“We’re sending our love down the well…”) He also helped dig Bart out himself.

Marge: “Sting, you look tired, maybe you should take a rest.”


Sting: “Not while one of my fans needs me.”


Marge: “Actually, I don’t know if I’ve ever heard Bart play one of your albums.”


Homer: “Shhh! Marge, he’s a good digger!” 

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Sting really dug being on “The Simpsons.”

Mr. Burns sold the nuclear plant, giving Homer the opportunity to meet some Germans and daydream about the land of chocolate.

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Sweet! Homer’s trip through the land of chocolate.

But the highlight of the season was Michael Jackson’s uncredited guest spot as a psychiatric patient who thought he was. . .Michael Jackson.

SEASON FOUR

The classics started stacking up. 

Homer ran the union and they went on strike, so Burns and Smithers took over. 


Marge played Stella in “A Streetcar Named Desire,” sending Maggie to daycare for the first time. 


In a nod to The Music Man, a charming, singing scam artist brought a monorail to Springfield, and randomly chose Homer to become its conductor. 


In another career switch, Homer became Mr. Plow. 


And the best of all – sadly not on YouTube – Homer formed his own religion, which meant he could skip church with God’s permission.


The Simpsons Photo

It’s hard to pick a favorite moment on this one. Is it Homer as a toasty cinnamon bun while the family freezes away in church? Homer as a saintly figure with birds and animals in the shower with him? The brave and heroic Ned Flanders rescuing Homer from the fire? Reverent Lovejoy responding to Apu’s declaration that there are 700 million Hindus with “That’s swell”? Or is it Homer’s conversation with God, while Jimi Hendrix and Benjamin Franklin play ping pong behind them in heaven? You tell us. 

SEASON FIVE

Bart got an elephant. He named him Stampy. 

Homer’s relationship with God remained complicated when he started liking Flanders, which didn’t last long. (He still likes ceiling waffles.) 


He was tempted to stray from Marge with the lovely Mindy Simmons (voiced by the lovely Michelle Pfeiffer), even though it made him sad. 


And he also made it into outer space, traveling with the real Buzz Aldrin.


Best of all, Sideshow Bob came back in an awesomely stupendous Cape Fear tribute, which included a salute to Gilbert & Sullivan. 


SEASON SIX 

These were busy times. Marge became a police officer, Lisa got a rival and saw her future, Bart discovered a comet, and Sideshow Bob came back yet again, this time to run for office: 


But he got caught. 


Homer joined the Stonecutters, who were led by a protocol-loving, Patrick Stewart.

Patrick Stewart’s “Simpsons” cameo.

And he surprised everyone by pursuing the dream he’d apparently always been denied. 

The Simpsons’ dog, Santa’s Little Helper, had a whole lot of puppies with another dog from the racetrack, leaving the Simpsons’ house overrun. 


Not to be missed, but not on YouTube: Mr. Burns’ song about how he wants to use the puppies to make himself an exotic vest. (If you find it, don’t send it to PETA.)  

SEASON SEVEN 

Twenty Two Short Films About Springfield was a series of lightly interwoven skits written by twelve different writers. It took its inspiration from Thirty Two Short Films About Glenn Gould as well as Pulp Fiction. There are really 19 stories in it, not 22, and we’ve got one of them. 


Bart sold his soul (and Lisa bought it back for him), George and Barbara Bush became The Simpsons’ neighbors, The Flanderseseses took the Simpson kids into their loving foster care, and Sideshow Bob came back, once again failing to kill Bart. Homer replaced a vacationing Smithers, went on tour with the Smashing Pumpkins, and learned that getting really, really fat would save him a trip to the office. 


Lisa became a vegetarian, making fast friends of Paul and Linda McCartney. It was a lonely journey, though. 


And with some help from an etherized Mr. Burns, Homer started a bowling team.


The yearly clip show had become a staple by then, but this time it was hosted by Troy McClure (Phil Hartman).


What? Who’s Troy McClure? Perhaps you remember him from his appearance in. . .all of these: 

SEASON EIGHT

Is Sideshow Bob back? Of course! This time he brought his brother (David Hyde-Pierce, in a nod to Frasier), and actually saved Bart’s life, for a change. 

Bart fell in love with his new neighbor Laura (Sara Gilbert), while Homer tried to sue an “all you can eat” restaurant for false advertising, with the help of Phil Hartman’s Lionel Hutz. 


Homer’s activities brought Dana Scully (Gillian Anderson) and Fox Mulder (David Duchovny) all the way to Springfield to investigate. 


But you can’t blame him for thinking he’d seen something X-Files worthy: 


Marge branched out, and started doling out advice as “The Listen Lady”.


Albert Brooks, longtime friend of Simpsons co-creator James L. Brooks, made his fourth appearance on the show, this time as Homer’s new boss, supervillain Hank Scorpio.  

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Homer’s supervillain boss Hank Scorpio.

This was the year we got one of the crown jewels of all Simpson episodes. Homer went on a metaphysical journey and met his spirit guide (voiced to perfection by Johnny Cash), after trying to prove his chili-eating mettle by swallowing a couple of insanity peppers. Marge really did do her best to stop him. . . 


Oh no! We almost left season 8 without mentioning Frank Grimes. Poor old Frank. 


RIP, Grimey. 

SEASON 9

So many great episodes, so few adequate words to describe them.

We got a great production number, “The Garbage Man Can,” when Homer became the Sanitation Commissioner. U2 even joined in! 

Homer in “The Garbage Can Man” production number.

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U2 raises some brew.

Homer got the family to join a cult, helped a lovestruck Moe by stealing his car, climbed the Murderhorn with the help of some Powersauce bars and some hardy sherpas, and took on New York City. (He lost.)

Bart and Lisa became TV reporters (where Lisa had cats thrown at her by a crazy lady), got stranded on a desert island with their schoolmates, and tried befriending Ralph Wiggum. 

Seymour Skinner admitted that he’d been living under a false identity for years, the Simpsons won their friends’ hearts and then their contempt at Christmas when Bart burned down the tree and all of their presents, and Lisa’s stab at independence by heading to the museum on her own went terribly wrong when she got lost. At least she had Homer out there to save her:


Homer and Marge put a little spark in their sex life, which seemed like a good idea at the time …


And we got what might be one of the best scenes in one of the best Simpsons episodes of all time, when an impatient Homer buys himself a gun. Careful there, Annie Oakley! 


If there was an award for best use of a Tom Petty & The Heartbreakers song ever, in anything, it would go to this:


Season 10 gave us Homer’s pet lobster Pinchy, and his new identity as Max Power, as well as his brilliant invention of the make-up gun, but the golden era was winding down. The show’s still incredibly popular, scores brilliant guest stars, and makes viewers happy week after week, but it’s Season 2-9 that shine the brightest, making you not want to miss a minute. For some of us, they’re the defining seasons of our generation. It’s like the moon landing!