The 20 Best Episodes of 20 Years of The Best Show Ever
Yesterday marked the 20th anniversary of the airing of the first episode of The Simpsons. In the 20 years since December 17, 1989, we have been invited into the home of America’s favorite family. In all that time Homer has gone to space and won a grammy, Bart became a national icon and bought a factory, Lisa saved her brother’s soul and fought the 8th amendment, and Marge has become a cop, a body builder, an artist, a chef, and a carpenter among many others. Hell, even Maggie shot an old man.
No show has the kind of quality and quantity of shows as The Simpsons. In compiling this list, I made a list of every episode that I loved, and it was 132 episodes long. When I shortened it to the classics, it was still 77 episodes long. Save for Seinfeld, no show in the 90’s came close toThe Simpsons at the height of their reign from Season 4-Season 8. This is the hardest list I’ve had to compile, but one I fully stand by, so please enjoy and here is to hoping for another 2 decades at 742 Evergreen Terrace.
- 20. Behind the Laughter (Season 11)
A perfect satire on Behind the Music and the show itself. - 19. Grade School Confidential (Season 8)
Getting to see the auxiliary character get strong, funny stories is always a highlight. - 18. The Wizard of Evergreen Terrace (Season 10)
For all the dopiness that Homer is known for, it is when he is trying his hardest to achieve something that usually leads to the funniest and most honest stories. - 17. I Love Lisa (Season 4)
One of the great secondary character episodes, with probably the most popular secondary character. - 16. The Dad Who Knew Too Little (Season 14)
The last truly classic episode. The dynamic between Homer and Lisa has led to many great episodes, with this displaying it at its best. - 15. The Joy of Sect (Season 9)
Religion has always been a big topic for the show, and I would argue none are funnier than this one. - 14. Bart Sells His Soul (Season 7)
We get to see the deeper side of Bart and just a lot of hilarious Milhouse. - 13. Homer The Great (Season 6)
Homer being an idiot never was so good. - 12. 22 Short Films About Springfield (Season 7)
The Simpsons has tried different storytelling styles over the years, the more recent episodes failing to come close to the genius of this episode. - 11. Homer’s Barbershop Quartet (Season 5)
A Simpsons episode inspired completely by the Beatles? Can’t not be good.
- 10. Bart of Darkness (Season 6)
This Rear Window spoof is the best of the many spoofs over the last 450 episodes. - 09. Itchy & Scratchy Land (Season 6)
Itchy & Scratchy led to many great episodes, none better than this action packed classic. - 08. The City of New York vs. Homer Simpson (Season 9)
Homer’s tortured past and present with NYC, along with great riffs on the things that symbolize the world’s most famous town put this near the top. - 07. Marge vs. the Monorail (Season 4)
Conan O’Brien (you know him?) wrote what many consider the high point of the show, especially with the fantastic music that the show has displayed over the years. - 06. Bart After Dark (Season 8)
This episode has so many fantastic lines and sightgags that it has to be in the Top 10. - 05. Homer at the Bat (Season 3)
An episode made for my love of Baseball and The Simpsons, the terrible fates of all involved are legendary. - 04. Homer’s Enemy (Season 8)
Someone finally calls out Homer for his laziness and stupidity, but you can’t help but love Homer more after all of it. - 03. Homer’s Phobia (Season 8)
The Simpsons and social commentary go hand-in-hand and never was it played better than this hilarious episode.
- 02. And Maggie Makes Three (Season 6)
For me, The Simpsons is never better then when it blends its humor with pitch perfect sincerity. So touching, I actually cried at the end. - 01. You Only Move Twice (Season 8)
It doesn’t get better than this play on James Bond and the new fangled Silicon Valley Billionaires. Each beat of this episode is sheer brilliance.
