Ay, caramba! The Simpsons is a treasure trove of endlessly iconic moments, bursting with heart, humor, and deliciously savage satire. There’s a reason writers always say, “The Simpsons did it first” and it’s because they did! Since its first episode in 1989, The Simpsons have explored so many facets of contemporary family living. From marriage troubles to new jobs, The Simpsons have done it all, and done it well.
It’s why we feel such a strong connection to the family because, in a sense, they are our family. We’ve been with them for 33 years now, and although the series is well past its golden years, that doesn’t mean it’s unwatchable.
Even the occasional modern episode is capable of doing something new, subverting our expectations, and making us laugh until our stomach hurts. That being said, we’re only counting Seasons 1 – 10, because they’re, by far, the most lucrative seasons. They’re David Bowie Hunky Dory tier. Let’s do this thing.
Season 1 – Roasting on an open fire (Episode 1)
This Christmas episode was chosen as the pilot for good reason. It’s the perfect introduction to the Simpson family, showcasing each characters’ flaws, strengths, and motivations to hilarious effect.
Best Line: “Jingle Bells, Batman Smells, Robin laid an egg. The Batmobile broke its wheel, Santa got away”
Season 2 – Bart The Daredevil (Episode 8)
A reckless Bart brings out the best (and most entertaining) sides of Homer, as we watch him fall down a cliff, not once, but twice, in order to teach his son a lesson. D’oh indeed.
Best Line: “You think you got guts? Try raising my kids”
Season 3 – Flaming Moe’s (Episode 10)
Moe the local bartender definitely operates on the shadier side of the business. When he steals Homer’s drink and skyrockets to stardom, we learn two valuable lessons. 1. Don’t betray your friends. 2. Fame is fleeting.
Best Line: “They say everyone can float in the Dead sea, but Selma sunk right to the bottom”.
Season 4 – Last Exit To Springfield (Episode 17)
There isn’t a second wasted in Last Exit To Springfield. Commonly cited as one of the all-time best episodes, Homer’s battle against Mr. Burns brings out the bizarre at every turn. A child needing braces has never, and will never, escalate this ridiculously ever again.
Best Line: “This is a thousand monkeys working at a thousand typewriters. Soon, they’ll have written the greatest novel known to man. Let’s see. It was the best of times, it was the “burst”, of times?! You stupid monkey!
Season 5 – Cape Feare (Episode 2)
Sideshow Bob gets hit by a rake. Many times. Bart almost gets killed. Homer is as useful as a mullet. It’s brilliant.
Best Line: “Very well Bart. I will send you to heaven before I send you to hell”
Season 6 – And Maggie makes three (Episode 13)
A wholesome, family-focused episode in which Homer explains why there are no photos of Maggie in the house. The reason why is so heartwarming and perfect; a reminder that The Simpsons functions best when it balances absurdity with heart.
Best Line: “You’re a pin monkey? Wow! Finally I don’t have to be ashamed of my father’s job”.
Season 7 – 22 Short Films About Springfield
Gazing over Springfield, Milhouse and Bart wonder what its motley citizens must be up to. For Principle Skinner, it’s burning down the house and feeding his boss Krusty Burgers. Wait, sorry. Steamed Hams. You have to watch it to understand.
Best Line: “Aurora Borealis? At this time of year, at this time of day, in this part of the country, localized entirely within your kitchen?”
Season 8 – Homer’s Enemy
It takes 8 seasons for us to meet THE anti-Homer, but it’s well worth the weight. Frank Grimes is the polar opposite of Homer, so when they meet, prepare for a firework-explosive collision.
Best Line: “A dream house, two cars, a beautiful wife, a son who owns a factory, fancy clothes, and lobsters for dinner! Do you deserve any of it? No!”
Season 9 – The City of New York vs. Homer Simpson
Speaking of Homer’s opposites, it’s unsurprising that New York is everything Homer isn’t. Competitive, swift, and compact, Homer struggles to even pay for a parking ticket during his family adventure at the big apple.
Best Line: “Now remember, criminals, prey on small-town folk like us. So if anybody asks, we’re sophisticated millionaires from the Ozarks”.
Season 10 – Mayored To The Mob
The Simpsons have had some stellar cameos throughout its run. Michael Jackson, Paul McCartney, the list goes on. For this episode, we get the one and only Mark Hamill, not to mention some outrageous Quimby antics.
Best Line: “Hey, thanks, everybody. You know, I’m here today as Luke Skywalker, but I’m also here … to talk about Sprint”.