The Simpsons has been on for 30 seasons, which means that the series has certainly had its ups and downs when it comes to the quality of its episodes. All in all, most fans will agree that some of the best episodes of the more recent seasons don’t really equate to the series’ earlier years. However, every season still had its own highlights, which must be celebrated.
On this list, we are choosing the funniest, most interesting, and/or most memorable episode of each season. Then, we are ranking each of those best episodes against one another. Read below to find out how the highlight of each season stands against the other seasons!
SEASON 30 - “BABY YOU CAN’T DRIVE MY CAR”
On “Baby You Can’t Drive My Car,” the fifth episode of season 30, we see Homer getting a job at CarGo, which is a self-driving car company that moves to Springfield. During the episode, we see Homer – and Springfield as a whole – hilariously coming to grips with this new company and technological advancement.
SEASON 28 - “THE TOWN”
On season 28, The Simpsons did a parody of Ben Affleck’s second film as a director, 2010’s The Town.
During this “The Town” episode, Bart is found cheering for a football team based in Boston, which happens to be Springfield’s rival team. Consequently, an annoyed Homer takes the family to Boston in an attempt to show to Bart how terrible the city and its people are.
SEASON 24 - “TREEHOUSE OF HORROR XXIII”
Season 24’s “Treehouse of Horror XXIII” was a parody of both Paranormal Activity and Back to the Future. During the episode’s “Unnormal Activity” segment, we see a collection of home videos from the Simpsons household being seemingly haunted. Then, Bart time-travels to 1974 and sees his parents as young people during the “Bart & Homer’s Excellent Adventure” segment.
SEASON 22 - “ANGRY DAD: THE MOVIE”
All the back on season 13, Bart created the character of Angry Dad, which was inspired by Homer, his often-irate father. Many years later, on season 22, The Simpsons aired the “Angry Dad: The Movie” episode, where Bart is able to turn this character into a movie.
It is hard to argue against the fact that “Angry Dad: The Movie” stood out from the other episodes on season 22. Not only was the episode hilarious, but it also felt like a huge payoff for a long-running storyline (Bart’s work on the Angry Dad character) in the series.
SEASON 20 - “SEX, PIES, AND IDIOT SCRAPES”
The St. Patrick’s Day-themed “Sex, Pies, And Idiots Scrapes” episode was certainly the highlight of The Simpsons season 20. In it, Homer and Flanders form a questionable duo of bounty hunters, and Marge finds a job at an erotic bakery.
This episode was not only a critical success, but it was also responsible for one of the show’s highest ratings during that 2008-2009 season.
SEASON 21 - “TREEHOUSE OF HORROR XX”
On “Treehouse of Horror XX,” we first see a Hitchcock-inspired segment where Lisa finds herself in a murder scene. Then, Springfield is overrun by zombies in the next segment. Lastly, the episode closes with a Sweeney Todd parody where Homer’s blood is used to brew beer.
SEASON 16 - “DON’T FEAR THE ROOFER”
The premise of the “Don’t Fear the Roofer” episode is simple: the roof is leaking at the Simpsons household, and Homer meets a roofer (at Knockers) who is voiced by Ray Romano. The twist? Well, it seems like nobody but Homer can actually see that roofer.
This very The Sixth Sense episode on The Simpsons is arguably season 16’s very best. At the end, Marge takes Homer to Dr. Hibbert, who declares him insane for seeing this mysterious roofer.
SEASON 15 - “TREEHOUSE OF HORROR XIV”
Season 15 started out with “Treehouse of Horror XIV,” which actually turned out to be the highlight of that season.
The segments on this The Simpsons Halloween special included Homer becoming the Grim Reaper, Millhouse getting a watch that can stop time itself, and Professor Frink bringing his father back to life. All in all, “Treehouse of Horror XIV” was watched by 16.22 million viewers, making it the most-watched Simpsons episode of that season.
SEASON 17 - “THE SEEMINGLY NEVER-ENDING STORY”
Based on The Neverending Story novel, this “The Seemingly Never-Ending Story” episode saw Homer and his family get stuck in a cage, where Lisa tells Homer a sequence of stories involving herself, Mr. Burns, Edna, and Moe.
There are many different stories in this episode, which is fitting for the title that it received. Season 17, which aired between 2005 and 2006, included a total of 7 holdover episodes that were originally slated to air on season 16.
SEASON 29 - “FLANDERS’ LADDER”
During this “Flanders’ Ladder” season finale, Bart is struck by lightning and then starts receiving visits from ghosts who are seeking closure. In the end, the episode even features a parody of the series finale of HBO’s Six Feet Under. All in all, “Flanders’ Ladder” brought an emotional arc to season 29 and the series as a whole.
SEASON 14 - “MOE BABY BLUES”
“Moe Baby Blues” is yet another season finale that really stuck out from the rest of the episodes. The episode tells the story of a lonely Moe who attempts to commit suicide, but ends up involuntarily saving Maggie’s life.
Not only is “Moe Baby Blues” one of those iconic moments where The Simpsons allowed itself to get a little deeper and more serious, but this episode is also held to a high regard by fans of the show. In hindsight, this finale made season 14 much stronger.
SEASON 25 - “BRICK LIKE ME”
The Simpsons goes LEGO on season 25’s “Brick Like Me.” This very fun and creative episode was brought to life through a LEGO style of animation where Springfield and the Simpsons family were shown in the form of bricks.
Despite the fact that the episode looks and feels nothing like The LEGO Movie franchise, the episode does reference those movies at the end. All in all, “Brick Like Me” will forever be remembered as one of the best times that the franchise explored a different animation style.
SEASON 13 - “POPPA’S GOT A BRAND NEW BADGE”
Season 13 was the first season with Al Jean serving as The Simpsons showrunner, a title that he still holds. The season 13 finale, “Poppa’s Got A Brand New Badge,” was certainly the standout episode of that year. In it, Homer caused an electrical blackout in all of Springfield, which somehow prompts him to start his own third-party police force.
SEASON 26 - “SIMPSORAMA”
The Simpsons and Futurama are both adult animated TV shows created by Matt Groening that air on Fox, so a crossover makes sense, right?
Well, the Simpsorama crossover episode didn’t happen until season 26, but it was definitely one for the books. During this episode, Bender attempts to kill Homer, but changes his mind later on.
SEASON 11 - “BEHIND THE LAUGHTER”
Season 11’s “Behind the Laughter” episode took a page from VH1’s Behind The Music, displaying The Simpsons characters taking fans on a fictionalized ‘behind the scenes’ on the making of the series.
Because this episode breaks the franchise’s overall continuity, it is considered by many fans as non-canon. In any case, “Behind the Laughter” is definitely considered one of the funniest and most creative The Simpsons episodes ever.
SEASON 19 - “ETERNAL MOONSHINE OF THE SIMPSON MIND”
Inspired by 2004’s Eternal Sunshine of the Spotless Mind, the “Eternal Moonshine of the Simpson Mind” episode shows Homer waking up and not remember what happened to him the day before. Throughout this season 19 episode, we watch Homer trying to piece things together with the help of Professor Fink and Moe.
SEASON 18 - “24 MINUTES”
Despite the fact that 24-inspired “24 Minutes” was originally slated to be the 400th episode on The Simpsons, it ended up airing as the 399th episode in the series. Featuring Kiefer Sutherland as a guest voice actor, this season 18 episode follows Bart and Lisa attempting to stop the school bullies from setting off a stink bomb at a bake sale.
SEASON 23 - “HOLIDAYS OF FUTURE PASSED”
Because the characters never actually age on The Simpsons, fans had always been curious to see how this family would turn out in the future. On season 23’s “Holidays of Future Passed,” we see the Simpsons family coming together for Christmas 30 years in the future. Homer and Marge are older, Bart and Lisa are parents, and Maggie is pregnant.
SEASON 10 - “MAYORED TO THE MOB”
Homer rescues Mark Hamill (dressed up as Luke Skywalker from Star Wars) during a sci-fi convention, and is then appointed as Mayor Quimby’s bodyguard. The premise of “Mayored to the Mob” is hilarious, and the episode certainly pays off, too. This is by far the highlight of season 10, kick-starting the next decade of this beloved TV show.
SEASON 27 - “BARTHOOD”
Inspired by 2014’s Boyhood, “Barthood” was a collection of flashback scenes taking place during Bart’s childhood. There is no doubt that this was the most interesting and memorable episode of season 27 of The Simpsons, with storylines that were both hilarious and heartfelt.