28 Episodes That Define The Simpsons 28-Year-Run

Premiering as a short on The Tracey Ullman Show in 1987, The Simpsons soon earned their own series two years later. Creator Matt Groening could have never have guessed that almost 30 years later this show would still be such a mainstay in pop culture. As a result of its popularity, The Simpsons has aired over 600 episodes to date. Impressive would be an understatement.

So with that many, you’ve got to wonder which is the best Simpsons episode of all time? While we can’t pick the ultimate #1, we can give you an episode from each season that has helped define the series and keep it going for almost three decades.

1. Season 1: “Simpsons Roasting On An Open Fire”

Because it was the first, we have to go with what is essentially the pilot episode. Set around Christmastime, we were introduced to the family in a full 30 minutes. Instantly we knew Bart was the bad boy, and while they had a nice house — finances weren’t always strong. As a result, Homer’s secondary job as a mall Santa eventually led them to their pup, Santa’s Little Helper. Setting the tone for the whole series, this is definitely one of the best Simpsons episodes.

2. Season 2: “Treehouse Of Horror”

This season had so many amazing moments it was really hard to choose. Trust, it was difficult to push the three-eyed fish and “Dancin’ Homer” to the side, but the most noteworthy of the entire second season had to be “Treehouse of Horror” because it started a long-standing tradition for the series. Every year from then on, The Simpsons‘ Halloween-inspired episodes were some of their most anticipated.

3. Season 3: “I Married Marge”

Let’s just note really quick that this season saw the introduction to the Flaming Moe, a drink we have all wanted since 1991. We also saw Bart’s BFF almost leave him for a girl! Not to mention they had THE Michael Jackson appear in their season premiere. All great, but not as good as “I Married Marge.”

The flashback episodes have always been special treats for the fans because they delivered a look into the past of these characters we’d come to love. An origin story on any level always works.

4. Season 4: “Marge Vs. The Monorail”

No one is ignoring the fact that both Bart and Lisa’s love lives shined this season. Well, sort of. Bart’s heart was broken by his babysitter while his sister broke the heart of Ralph Wiggum after a misinterpreted Valentine’s Day card.

We’re just saying that the musical number in “Marge vs. the Monorail” is the absolute best. Written by Conan O’Brien, this episode will forever play on a “best of” reel of this show.

5. Season 5: “Lisa Vs. Malibu Stacy”

The Simpsons is no stranger to tapping impeccable talented guest stars. This season they had musical legends like The Ramones and George Harrison of The Beatles, but it was Kathleen Turner in “Lisa vs. Malibu Stacy” that stole the show. Lisa has always been the animated definition of girl power. A hero for many young women for years, she tried to fight the patriarchy in this episode. She may’ve lost, but lessons were definitely learned.

6. Season 6: “Who Shot Mr. Burns? (Part One)”

Do you know how hard it is to walk through memory lane, especially when it’s lined with so many fantastic TV moments? Season six was on point y’all. We saw the future with “Lisa’s Wedding” and learned that toilets down under flushed the other way in “Bart vs. Australia.” The best, though, is the thrilling setup in “Who Shot Mr. Burns (Part One).” This kept us guessing ALL summer long. We won’t spoil it in case you never solved the case.

7. Season 7: “Homerpalooza”

A lot of great things happened during this season. We found out who shot Mr. Burns. Lisa became a vegetarian and talked to Paul McCartney about it. Finally, The Simpsons did their take on Lollapalooza with Hullabalooza. An ode to a signature music festival of the ’90s, it was a perfect homage along with guest stars, The Smashing PumpkinsCypress HillSonic Youth and Peter Frampton.

8. Season 8: “The Springfield Files”

One could not exist in the ’90s without showing some love to The X-Files. Homer and Bart’s run-in with an “alien” that turned out to just be Mr. Burns after a cascade of medical treatments was beyond perfect. Plus, you can’t beat having David Duchovny and Gillian Anderson in an episode. Oh yeah, and the late Leonard Nimoy narrating. ICONIC.

9. Season 9: “Natural Born Kissers”

Things got a little naughty at the end of season nine with “Natural Born Kissers.” After Homer and Marge realize that getting down and dirty in public is intoxicating, they cannot stop. Of course, this leads to a very uncomfortable instance at a mini-golf course. It was an eye opening experience for fans of every age.

10. Season 10: “Simpsons Bible Stories”

Because they aren’t so in your face with it, you kind of forget that, at the core, The Simpsons are a faithful family. God has appeared in the series a handful of times. They also attend church quite regularly. Without being preachy, this episode from their tenth season showcased where The Simpsons stood in religious terms without crossing any sort of Joel Osteen lines.

11. Season 11: “Alone Again, Natura-diddily”

If a television show doesn’t shock you at least once during its run, it’s not done its job. The Simpsons did just that when Ned Flanders became a widower in this one. Basically everyone in the world was like ‘WTF?!‘ It changed the course of Ned’s character forever while proving that life does go on after losing someone.

12. Season 12: “New Kids On The Blecch”

The year was 2001. Boybands were still the best thing about music. The result? NSYNC fans got a look at what their faves looked like all animated and yellow. Plus we got to see Bart and Co. do their thing in their own rendition of a boyband as well.

13. Season 13: “I Am Furious (Yellow)”

The 13th season kind of went there. Homer had medical marijuana and wound up bootlegging sugar after Springfield banned it. All sweet and great, but Stan Lee guest starring in “I Am Furious (Yellow)” was top notch as we were introduced to “Angry Dad;” Bart’s comic book inspired by his own angry dad.

14. Season 14: “Large Marge”

Homer moving out and into a gay neighborhood was solid, but we have to go with “Large Marge” as the best episode of the season. When the animated mom opted for plastic surgery, it made real-life headlines. It would be only six years later that she then appeared on Playboy. Yup, THE Playboy.

15. Season 15: “Milhouse Doesn’t Live Here Anymore”

Anyone with siblings knows that Bart and Lisa’s relationship isn’t overly dramatic. We can really get on one another’s nerves. We also know that at the end of the day, they are natural best friends. We got to see that friendship between Bart and Lisa when he was left alone after Millhouse moves away and after 15 seasons, we needed that.

16. Season 16: “All’s Fair In Oven War”

One episode in their 16th season had Tom BradyWarren SappLeBron JamesYao Ming and Michelle Kwan. Damn. That wasn’t the best though. That title belongs to “All’s Fair in Oven War.” It was during that episode when we saw Marge’s very dark side as she sabotaged a cooking contest and we kinda dug it.

17. Season 17: “Marge’s Son Poisoning”

This was the season that introduced us to Sideshow Bob’s wife and son, but it was also the one with “Marge’s Son Poisoning.” A bonding episode for mothers and sons everywhere. Sometimes an episode can just be simple and sweet and still compete with some of the hectic and chaotic ones.
Simplicity, another reason this show has remained on top for 28 seasons.

18. Season 18: “24 Minutes”

Pairing with other FOX shows was nothing new to The Simpsons. They did it before with The X-Files and then again with 24 in “24 Minutes.” Kiefer Sutherland and Mary Lynn Rajskub were obviously included in the package as they helped Bart and Lisa save their school’s annual bake sale. 24 was such a hit show at the time that this just seemed like SUCH a big deal for Simpsons fans and 24 fans alike.

19. Season 19: “Funeral For A Fiend”

Sideshow Bob had been stealing the show for a while by this time. Every time he tried to kill Bart was as hilariously evil as the last, but “Funeral for a Fiend” gets a special shoutout because Bob’s whole family was involved in the action. In addition, this episode also stood out because Kelsey Grammer was reunited in the animated realm with his Frasier family as David Hyde Pierce and John Mahoney both guest starred as well. Yeah, remember Frasier?

20. Season 20: “Lisa The Drama Queen”

It’s not that this episode saw Lisa losing her grasp on reality, or that it guest starred Emily Blunt and Fall Out Boy that made this episode the best one of season 20. Nope, this episode was special because it was the last one to air with the old opening that the show had used since the second season. It was really a turning point of the show and at that point, we knew it.

21. Season 21: “The Color Yellow”

2010 was the year we learned that Homer Simpson wasn’t just a yellow dude. “The Color Yellow” taught us that Homer was actually a descendent of a black slave long down the line in his family tree. An interesting twist to their story? For sure.

22. Season 22: “The Ned-liest Catch”

Homer partners up with Cheech Marin, Aunt Selma marries into the mob, and there is a Glee-inspired episode. The most surprising of the season came at the end, though, when Ned Flanders starts dating Edna Krabappel in “The Ned-Liest Catch” because literally NO one would’ve paired them together and we love a good plot twist.

23. Season 23: “Lisa Goes Gaga”

No stranger to superstars, The Simpsons has had a few dozen over the years. They may have outdone themselves in 2012 when they tapped Lady Gaga for this episode where she helps Lisa overcome being the outcast of Springfield Elementary. It was a touching episode that not only spoke out against bullying the unpopular kid but also went with Gaga’s ongoing message of inclusiveness.

24. Season 24: “dangers On A Train”

There have only been a few times since the beginning where we really felt like Homer and Marge were over and done with. This was the biggest though. Marge went and caught feelings for another man? This was stressful for longtime watchers from beginning to end.

25. Season 24: “Married To The Blob”

It can be hard for a show that has so many side characters to showcase them all. That’s why you have to love when they shine a light on anyone who’s not in the immediate Simpson family. Which is what they did in “Married to the Blob.” The Comic Book Guy has had a few storylines in the past, but this one seemed to give him the most heart.

26. Season 26: “simpsorama”

Superfans know that Simpsons’ creator Matt Groening is also the mind behind Futurama. So when those futuristic characters made their way to Springfield, awesomeness ensued. Fans were left very, very happy seeing Bender and Homer in the same realm. More crossovers, please!

27. Season 27: “The Burns Cage”

Smithers finally realizes it was time to move on from Mr. Burns after his elderly boss just doesn’t care about him the way he needs. So the rest of Springfield offers to find Smithers a man. It’s great because we finally got to really see this character out and about after so many years of wondering. A fabulously done episode based on a longtime favorite.

28. Season 28: “Kamp Krustier”

When it’s been almost 30 years of a show, it feels like a treat when the story decides to revisit the past. We’re reminded of an episode from way back in their fourth season called “Kamp Krusty” when “Kamp Krustier” came out — and this one picks up where that one left off. Picking up 20 years later could’ve been massively confusing BUT because time never really passes in The Simpsons’ world — it worked.

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