The Simpsons has been on television for 25 years. Stop and think about that for a minute or two.
It doesn’t matter that the show’s Golden Age passed more than a decade ago or that Homer, Marge and their never-aging children were at best the silver medalist in FOX’s Animation Domination Sunday night line-up. Anyone that watched this show early in its run heard from their parents that it was stupid to have cartoons on in prime time and that it would never last. Well, The Simpsons has outlasted every other television show of the last 20 years and though they might have overstayed their welcome, the show has undeniably delivered some iconic episodes over the years.
Thanks to Buzzfeed’s outstanding list of 29 Jokes Only “Simpsons” Fans Will Find Funny, the royal family of animation is getting featured in this week’s edition of The Rundown.
Let us know your favourite episodes – hit us in the comment section or tell us on Twitter: @AmongMenMag
Marge vs. The Monorail
Hands down the best episode of all time. It’s not even close. From Homer’s opening take on the theme song from The Flintstone’s (“Simpson. Homer Simpson. He’s the greatest guy in history. From the town of Springfield, he’s about to hit a chestnut tree.”) to Lyle Lanley conning the town out of millions of dollar by selling them a faulty, possum-filled monorail, this is one of the most iconic episodes in the show’s lengthy run.
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Last Exit to Springfield
Dental Plan. Lisa needs braces. Dental Plan. Lisa needs braces. The name of the episode itself might not ring a bell, but Homer’s turn as the union rep at the Power Plant and Lisa’s Jack Nicholson as The Joker moment are etched in every Simpsons fan’s memory. Homer desperately searching for a bathroom in Mr. Burns’ mansion and answer, “Um… yeah” when asked if he found one is simple genius.
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The Itchy and Scratchy and Poochie Show
Ah Poochie the Dog, such an iconic “inside baseball” (read: what now gets called meta) nod to the way television shows often try to fend off a case of the stales (or even cancellation) by introducing someone new and hip into the mix. Of course, the creative team wasn’t afraid to poke fun at themselves either, introducing The Simpsons’ new house guest, Roy, into the fold at the start of the episode. Thankfully, Itchy and Scratchy got back to beating the hell out of each other and Poochie rocketed back to his home planet, dying on the journey. Oh, and Roy moved out too.
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Flaming Moe’s
“Mr. McStagger is here?!” There’s a lot of awesomeness contained in this episode about flammable drink recipes stolen from a friend, but Moe’s reaction to the alcohol rep wanting to purchase his recipe has always stood out. So too did the guest appearance by Aerosmith. That may not seem like a big deal now, but the episode aired in 1991 following the massive success of Pump and during the days when famous people didn’t do guest spots on cartoons.
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Bart the Lover
Stuck in detention, Bart decides to torment Mrs. Krabappel with fake love letters from a fabricated admirer (and Gordie Howe doppelganger) named Woodrow, taken from President Woodrow Wilson, but it stops being fun when he sees his frequent adversary heartbroken after Woodrow never turned up for their dinner date. A sweet farewell letter finished with smooth words from “The Old Honey Dripper” Homer J. eases Edna’s pain. An extra bonus about this episode is Tod Flanders learning to swear and Homer trying not to as he builds a dog house.
NEXT: 5 more iconic episodes of The Simpsons…

E. Spencer Kyte
E. Spencer Kyte is a freelance journalist based in Abbotsford, British Columbia, where he lives with his wife and dog. In addition to his work here, he writes about sports for Complex Canada and covers the UFC for various outlets. His mom also still tells him what to do on a regular basis, even though he’s nearly 40. He tweets from @spencerkyte.