At this point, The Simpsons is almost synonymous with American culture. Currently in its 35th season, the show has been premiering new episodes since 1989 – and currently has more than 750 episodes under its belt, making it the longest-running prime-time show in television history. Add to that the franchise’s numerous hit video games, the 2007 movie that grossed more than $536 million, and its very own ride at Universal Studios, and you have one of the most successful franchises ever.
But The Simpsons has definitely had some lulls throughout the years as well. For a period, the series had developed a reputation for not being as good as it used to be and for relying too heavily on entire episodes that lazily spoofed something in the zeitgeist. Luckily, the show has restored its reputation with its last few seasons and has returned to its roots of biting satire and commentary on American life while also providing lots of humor and heart along the way. But what are the best seasons of The Simpsons that offer the greatest episodes and most iconic moments?
10. Season 34 (2022-2023)
One of The Simpsons‘ newest seasons is also one of its best. After years of somewhat lackluster episodes, season 34 provided tons of clever spoofs and smart satire. In this season, fans were even treated to two Halloween episodes. There was the annual Treehouse of Horror episode, which this time around lampooned Westword and Death Note in a unique anime style. The episode received lots of praise and even won an Emmy for Outstanding Animated Program. On top of that, there was an entire episode dedicated to Stephen King’s It.
Other highlights in the season included witty social commentary like Habeas Tortoise, where Homer falsely believes a tortoise has been stolen from the zoo and creates a Facebook group for conspiracy theorists to figure out who stole it. The episode clearly mocked the rise of conspiracy-obsessed fanaticism fostered by social media, proving that The Simpsons was still as brave and sharp as ever and wasn’t afraid to call out America for what it is.
9. Season 2 (1990-1991)
First and foremost, season 2 deserves massive credit for one simple reason: This is when audiences got their very first Treehouse of Horror episode, and that episode marked the first appearance of the alien duo Kang and Kodos. Since then, Treehouse of Horror has become an annual favorite and remains one of the most popular episodes each season.
On top of that, season 2 also had Bart vs. Thanksgiving, one of the very few Thanksgiving-themed episodes in the show’s history. But most famously, season 2 had Bart the Daredevil, where Bart enjoys the attention he gets from doing stunts, so he decides to jump the Springfield Gorge on his skateboard. But in the end, it’s Homer who famously finds himself going over the gorge … and then crashing down to the bottom.
8. Season 33 (2021-2022)
Season 33 was notable because it was the first season in a long time where The Simpsons began receiving praise again. The season was loaded with enjoyable episodes like The Star of the Backstage, where Marge puts on a local theater production, and Bart the Cool Kid, which poked fun at influencer culture. But the real star of the season was its finale, Poorhouse Rock.
The episode exposed the problems of America’s economy and revealed how those in powerful positions have rigged the system to turn the middle class into the working poor. The grand conclusion was the spot-on musical number Goodbye Middle Class sung by guest star Hugh Jackman. Also joining in on the song was former U.S. Secretary of Labor Robert Reich, who sang about how automation, offshoring, and the lie of trickle-down economics destroyed the prosperity of America. The episode made no attempts to be subtle and instead said exactly what it wanted to, proving that The Simpsons was as fearless as ever.
7. Season 23 (2011-2012)
Season 23 came out during a rough period for The Simpsons. The series by this time had developed a pretty negative reputation during the 2010s, with many saying the series had lost its magic and wasn’t good anymore. Luckily, season 23 proved that the show still had some spark.
It had tons of great spoof episodes like Exit Through the Kwik-E-Mart, Them, Robot, and The Doh’-cial Network, but the true strength of the season came from original stories like A Totally Fun Thing That Bart Will Never Do Again. In the episode, the Simpsons have the time of their life on a cruise and Bart realizes how fleeting great moments are … so he decides to sabotage the cruise to make it last forever. Without giving away any spoilers, the episode ends with the Simpsons sliding down snow mounds with penguins as Winter’s Love by Animal Collective plays. Somehow, it became one of the most emotional and touching scenes in Simpsons history.
6. Season 13 (2001-2002)
Season 13 had tons of great episodes, but the two most notable are both holiday-themed. There was Treehouse of Horror XII, which hilariously parodied 2001: A Space Odyssey (with Pierce Brosnan voicing the HAL-like AI) and Harry Potter. In the Harry Potter segment, Bart and Lisa both attend magic school and naturally, Bart slacks off … resulting in him creating a frog monster that’s an absolute abomination against nature. As it begs for death, you can’t help but feel mortified as you laugh your butt off.
The season also had the Christmas episode She of Little Faith, where Lisa rejects the commodification of Christianity and decides to convert to Buddhism. The episode guest-starred Richard Gere and was shocking upon its release in 2001, because it was still considered offensive to call out Christianity on broadcast television (especially in a cartoon). But the episode was also a powerful commentary on religion’s faults and, despite its controversy, She of Little Faith was well-received by critics and nominated for an Emmy.
5. Season 6 (1994-1995)
Filled with humor and heart, season 6 had a lot to offer. On the sad side, ‘Round Springfield saw Lisa lose her jazz idol Bleeding Gums Murphy. But after he dies, Lisa and his spirit perform a rendition of Carole King’s Jazzman. It was a touching and moving episode that proved The Simpsons could pull at your heartstrings even in its early seasons.
Other notable episodes include Bart vs. Australia and Treehouse of Horror V, which is one of the best Treehouse of Horror episodes ever. All three segments in the episode remain totally iconic and were spot-on hilarious and horrifying as they spoofed The Shining, A Sound of Thunder, and Soylent Green. Even the credits are hilarious as the Simpsons dance to A Chorus Line with their skin turned inside-out (you’ll just have to watch the episode to get it).
4. Season 5 (1993-1994)
Season 5 is one of the most iconic Simpsons seasons of them all. First off, Treehouse of Horror IV gave us Terror at 5 1/2 Feet, which hilariously spoofs the iconic Twilight Zone episode Nightmare at 20,000 Feet. This time around, a goblin is attacking the wheels of Bart’s school bus and nobody seems to believe him, driving Bart to madness. It’s hilarious and is a great homage to the original.
Also featured was Lisa vs. Malibu Stacy, which commented on the good and bad legacies Barbie (cough cough, I mean, Malibu Stacy) has left on the world. But most memorable of all was Cape Feare, the episode where Sideshow Bob gives us a rousing rendition of the musical H.M.S. Pinafore. Sideshow Bob might be a murderous mastermind, but he’s also one hell of a performer.
3. Season 7 (1995-1996)
Season 7 premiered with a bang … literally. The first episode of the season was the iconic Who Shot Mr. Burns Part 2. Spoofing Dallas, the episode revealed that Mr. Burns was shot by none other than Maggie Simpson. The episode was a massive event at the time and Fox even set up a contest where viewers could guess who the shooter was. From there, the season continued releasing fantastic episodes, like Scenes from the Class Struggle in Springfield, where Marge gets her hands on a discounted Chanel suit and tries to become a socialite. But with only one Chanel suit, she’s forced to hem it into different outfits daily.
But the most memorable episode has to be Two Bad Neighbors, where former president George H.W. Bush and his wife, Barbara, move across the street from the Simpsons. Bush had a long history of bashing The Simpsons and citing them as part of America’s moral decline. This feud helped inspire the episode that turned out to be both hilarious and charming.
2. Season 4 (1992-1993)
Sing it with me, “Monorail! Monorail! Monorail!” Marge Vs. the Monorail is one of the most iconic episodes in Simpsons history. Spoofing The Music Man, the episode was hilarious and tons of fun. A swindler comes to town (voiced by the late Phil Hartman) and sells the town on building a monorail system with his catchy musical number. Fun fact: The episode was written by Conan O’Brien. Another fun fact: The monorail plan ends in absolute disaster.
Season 4 also had the Emmy-winning episode Mr. Plow, where Homer and Barney become competing snow plow drivers, and the future-predicting episode Whacking Day. In the episode, Lisa is appalled that each May, Springfield has a celebration where they lure snakes to the middle of town and whack them to death with bats and mallets. Flash-forward and Whacking Day now takes place every day in the state of Florida, where invasive pythons are growing to almost 20 feet long and destroying ecosystems. You can even win money by killing pythons during the annual Florida Python Challenge.
1. Season 8 (1996-1997)
Season 8 is hands down the best Simpsons season of all time. It’s such a great season that there could be an entire article ranking all of its iconic, memorable, and downright fantastic episodes. First up, there was the epic X-Files spoof episode The Springfield Files. Both Gillian Anderson and David Duchovny guest-starred in the episode where Homer becomes convinced he’s seeing aliens. That year’s Treehouse of Horror was also iconic thanks to the segment The Thing and I, where Bart discovers he has an evil twin lurking in the attic. On top of being a great story, it also had some genuine scares.
But even more memorable was Bart After Dark, where Bart is forced to help out an old lady after he smashes her window … only to discover she runs a house of burlesque. The episode ended up winning an Emmy for its catchy tune We Put the Spring in Springfield. Season 8 also had the episode Homer’s Phobia, which guest-starred John Waters. In the episode, Homer befriends Waters, but later becomes upset after learning that he’s gay. The episode won an Emmy and became historic as one of the first times an animated series had a plot involving the LGBTQ community.
Looking for more Homer,Bart and company? Check out these classic Simpsons episodes,
