5. A Star is Burns (season 6, episode 18)
The episode: In a bid to improve the perception of Springfield, the town decides to put on a film festival.
Why it’s one of the best: God, I love this episode. Mr. Burns is at his tyrannical best here, trying his absolute best to rig a small-town film festival by throwing millions of dollars at an ego-fuelled production of his life. If that setup doesn’t make you chuckle, then how about the countless other homemade movies on display which allows half of Springfield to really shine? There’s Man Getting Hit by Football, The Eternal Struggle, and so much more besides that.
Each joke set-up quite easily could’ve been the high point for many a different comedy series. Not so for The Simpsons. Here, it was just another moment before an even bigger and better joke. The episode’s successes are summed up by one small throwaway gag: Boo-urns. It doesn’t make sense – much like a film festival being hosted in Springfield – but it didn’t have to, because the timing, set-up, and execution is all absolutely flawless.
It says a lot that this is an episode you can re-visit at any time, whether you’re watching the whole thing or just fancy a quick 20-second dip, and you’re going to be rolling around on the floor in fits of laughter, guaranteed. That’s the sign of a show at the top of its game.
4. Itchy and Scratchy Land (season 6, episode 4)
The episode: The Simpsons decide to go on a vacation to the newly-opened Itchy and Scratchy Land theme park. Chaos ensues.
Why it’s one of the best: We’ve all had a holiday go very, very wrong – but nothing quite like what goes down in "Itchy and Scratchy Land." Whether it’s Bart dialling up his prank game to 11, the Westworld-style meltdown of the robots, or the creative staff’s barbed digs at Walt Disney’s, ahem, dubious background, it all comes together to provide us with a riotous episode that allows the family to breathe away from the confines of Springfield.
It helps that every part of the trip is so relatable. You’ll groan along with Bart and Lisa as they pass the Flickey’s sign (probably the best sight gag in the show’s history), you’ll be embarrassed and want to be thrown in a (not-so-literal) hole just as Marge does after Homer and Bart’s shenanigans, and you’ll cheer as the family eventually bond as they come face-to-face with killer robots. Ok, maybe not that last bit. Still, this is one road trip you won’t mind revisiting again and again.
3. Bart's Comet (season 6, episode 14)
The episode: The end is nigh for Springfield as a comet hurtles towards the town.
Why it’s one of the best: It doesn’t appear that way at first – or even up until the episode’s final act, really – but this episode is a perfect marriage of what makes the (relatively) early years of the show so great as it makes your heart swell while also splitting your sides. Everything that comes before the final few minutes, where almost all the town gets crammed into Ned’s bunker, is exceptional (“There’s a 4:30 in the morning now?” Bart quips after being forced into early-morning science work with Principal Skinner), but Ned belting out the first few lines of Que Sera Sera elevates it into something even greater. He’s suddenly joined by the entire town, despite facing certain doom. Is someone chopping onions?
2. Last Exit to Springfield (season 4, episode 17)
The episode: Homer becomes union leader at the Power Plant and leads a strike to push through better benefits for the workers.
Why it’s one of the best: It was the best of times, it was the blurst of times. Don’t be fooled by the dry-sounding plot. Homer’s union antics very much play second fiddle to a show that decided it wouldn’t let something as flimsy as a plot get in the way of jokes. Often regarded as the show’s best (close here, but no dice), it’s not hard to see why everyone loves it thanks to the many cultural parodies, rambling Grandpa stories, and even some vaudeville-style innuendo.
What other show could mesh The Beatles, Jimmy Hoffa, Batman, and The Grinch into 22 minutes quite so expertly? The Simpsons, in its heyday, was something for everyone, yet this episode’s real skill was spinning so many plates at once and not having it all come crashing to the ground. It all ends with Homer getting one over his boss, too. That’s the dream.
1. Homer Badman (season 6, episode 9)
The episode: Homer undergoes trial by public opinion after allegations of sexual assault.
Why it’s one of the best: Homer Badman deals in serious issues – such as sexual assault and alarmist media coverage – and wraps it all up into a package worthy of topping any TV episode list, Simpsons or otherwise. It doesn’t take you to one side for a stern lecture, either.
The jokes, inevitably, come thick and fast (Homer’s obviously-edited interview to make him look bad is a definite highlight), but it’s the fact that it’s still as relevant today as it was a quarter of a century ago that sets it apart from all the others. Because that’s what The Simpsons does, and why it's the best Simpsons episode ever: it makes you laugh, it makes you cry, and, just sometimes, you can relate to it on a level that other shows daren’t even attempt to reach, let alone pull off with as much grace as The Simpsons does in "Homer Badman."