The 20 Best Seasons Of The Simpsons Ranked

"The Simpsons" is less of a TV show and more a force of pop-cultural nature. While the series has undergone many changes over the years and decades, it has never lost its perfect balance of satire, humor, and heart. Homer, Marge, Lisa, Bart, and Maggie have embarked on countless (mis)adventures, and yet audiences have never gotten tired of seeing the Simpson family stick together through all of the zaniness. What started off as a fun animated program about a wacky family that poked fun at sitcom cliches has since become a massive franchise whose influence can only be measured in terms of megatons, which is not surprising considering how long and with how many episodes "The Simpsons" has been entertaining us. 

As of this writing, the series has now tallied more than 720 episodes spread out over 30 seasons and has the unique distinction of being the longest-running sitcom in the U.S. That's not bad for something that got its start as animated short segments on "The Tracey Ullman Show" in 1987. Let's not forget about the hit 2007 film, either. While the popularity of "The Simpsons" has dwindled throughout its history, it's still going strong. Some mediocre seasons are to be expected for a series that has lasted this long, but overall the show has an incredibly strong legacy consisting of far more acclaimed seasons than middling ones. Let's take a look at the best seasons of "The Simpsons," ranked according to IMDB.

Season 17 doesn't go over and beyond with the laughs or originality, but it should be lauded for at least giving some extra attention to side characters. "Million Dollar Abie" is a Grandpa-centric episode, chronicling his blowing Springfield's chances of becoming the home for a professional football team. Feeling down after everyone in town hates him, he gets a new lease on life by becoming a matador. The plot is kind of all over the place, but it features some laugh-out-loud moments and fleshes out the relationship between Grandpa and Lisa.

"Treehouse of Horror XVI" continues "The Simpsons"' tradition of spoofing popular horror properties: "B.I. Bartificial Intelligence" has the Simpson family replacing Bart with a superior android son; "Survival of the Fattest" finds Homer and others going to Mr. Burns' property to do some hunting, only to be hunted by Mr. Burns himself; and "I've Grown a Costume on Your Face" has Springfield hosting a costume contest that goes awry for everyone in town.

Season 20 of "The Simpsons" is a pretty important one for the show, as it was when they tied with the "Gunsmoke" record of most seasons on the air. Unfortunately, despite a few good episodes, this season isn't remembered for much more than its milestone. The season opener, "Sex, Pies and Idiot Scrapes," is a standout, following Homer who ⁠— inspired by his recent stint in jail ⁠— decides to become a bounty hunter and brings along Ned Flanders for some hijinks. The episode also features Marge working at an erotic bakery, which shocks her more traditional sensibilities but she agrees to stay on when told she has a special talent for baking.

"Homer and Lisa Exchange Cross Words" does a nice job crossing two different storylines: Lisa becomes addicted to crossword puzzles and even participates in a crossword puzzle competition, while Homer makes big bucks breaking up couples ... only to get out of that business when he has nightmares about angry exes. So how do these two plots meet? Homer, noticing Lisa's wins at the crossword competition, bets the money he made from breaking up couples on Lisa which pays off big time. However, when Lisa begins to falter, Homer decides to bet on her opponent, much to Lisa's annoyance. However, this episode does a nice job harking back to that classic feel-good era of "The Simpsons."

While Season 15 isn't without some solid episodes, it was also proof that "The Simpsons" had lost much of its originality and was firmly in a more straightforward direction. A high point for the season was "The Regina Monologues," which saw the Simpson family head to London on the insistence of Grandpa, who wants to look up a woman he once hooked up with during his time in World War II. Of course, this being "The Simpsons" the episode isn't a travelogue and it isn't long before Homer crashes into the horse-drawn carriage of Queen Elizabeth II and is considered for execution.

The writers behind "The Simpsons" have fun with history in "Margical History Tour," which has a wraparound storyline about Marge giving botched history lessons to Bart, Lisa, and Milhouse when they discover that the library has gotten rid of most of their history books. Homer plays King Henry VIII (which of course features him singing "I'm Henry the Eighth, I am"), Lenny and Carl play Meriwether Lewis and William Clark, respectively, and the film "Amadeus" is referenced with Lisa as Salieri and Bart as Mozart.

One of the most memorable "Simpsons" episodes of Season 14 was "How I Spent My Strummer Vacation," which sees the Simpson family send Homer to a Rock 'n Roll Fantasy camp after they see him rant about how much they annoy him on TV. Not only does it feature a hilarious premise, but the episode also includes a bevy of rock star cameos including Mick Jagger and Keith Richards of the Rolling Stones, Lenny Kravitz, Elvis Costello, Tom Petty, and Brian Setzer.

Kelsey Grammer returns as Sideshow Bob in "The Great Louse Detective," when the character is ordered by Chief Wiggum to live with the Simpson family to help them discover who's been trying to assassinate Homer. Spoiler alert: it's Frank Grimes, Jr., the son of Homer's enemy who died while futilely trying to prove to the world how stupid Homer is. It's a pretty hilarious callback to a classic episode, and seeing Bart forced to live with his archnemesis is a blast as well. However, one of the season's low points is "A Star Is Born Again," in which Ned Flanders strikes up a relationship with a famous actress who is charmed by his old-fashioned ways. While Marisa Tomei makes a great addition as the actress, the episode feels rushed and Ned's actions feel out of character.

Homer gets lots of love this season with plenty of episodes focused on the big lug. It's a dream come true for Homer in "Guess Who's Coming to Criticize Dinner?" when he gets paid to eat at restaurants as a food critic (with Lisa writing the actual reviews, of course), but becomes the target of an attempted assassination when his negative reviews arouse the ire of Springfield's chefs. "E-I-E-I-(Annoyed Grunt)" has Homer take his family to live on the farm he grew up on, where he mixes tobacco seeds with tomato seeds to create the highly addictive "tomacco." In "Hello Gutter, Hello Fadder," Homer achieves some local notoriety when he bowls a perfect 300 game, but must contend with being seen as a flavor of the month.

Luckily, Homer leaves room for other characters to get the spotlight this season. Moe gets plastic surgery in "Pygmoelian," which leads to him getting the starring role in a soap opera, and Lisa learns tap dancing from a deranged former child star in "Last Tap Dance in Springfield." However, this season is marred by the death of Maude Flanders in "Alone Again, Natura-Diddily," which not only tries to cram too much story into a single episode but also feels like a contrived way to change up the status quo of the show.

Watching the inaugural season of "The Simpsons" today is an almost completely different experience from watching the show in its current form. The voices sound different (despite being provided by the same actors), the animation is rough compared to the modern polished style, and there's a lot more emphasis on character than gags and pop culture references. It's still a marvel how well-formed the show was when it first aired in 1989, and how many elements it introduced that have since become staples of the show for the following 30+ years. It's obvious that Matt Groening and company had a clear vision in their heads of how the show would look and the type of humor it had before that debut episode hit the small screen.

Speaking of the debut episode, "Simpsons Roasting on an Open Fire" was an auspicious start for the series. It saw the family struggling with financial issues around Christmastime, prompting Homer to get a second job as a department store Santa Claus. When that doesn't work out, he goes to the dog track for one last chance to make some money. That too fails, but he does return home with a new family member, Santa's Little Helper.

During this era of "The Simpsons," the show was still fairly grounded and largely consisted of believable storylines. While there were still some aspects that needed polishing, Season 2 was a considerable improvement on the inaugural season and featured a ton of heart that's been largely missing in later seasons. Because of Bart's immediate popularity, there were several episodes that focused primarily on him. Notable among these episodes is "Bart Gets an 'F'" which sees Bart's constant failures in school put him in jeopardy of repeating the fourth grade, and so he reaches out to class genius Martin Prince (marking the character's series debut) for help.

Homer's side of the family is explored in "Oh Brother, Where Art Thou?" which features Danny DeVito voicing his long-lost half-brother Herbert 'Herb' Powell. Dustin Hoffman guest stars in a moving episode as Lisa's substitute teacher Mr. Bergstrom, on whom she develops a crush. While the show was still in its relative infancy, it still managed to snag a cameo from a Beatle (namely Ringo Starr) in the episode "Brush with Greatness," which gives Marge a time in the spotlight as she explores her artistic side. Season 2 is also important for serving as the launchpad for several characters who would go on to become major fixtures in the show, including Maude Flanders, Nick Riviera, Hans Moleman, Julius Hibbert, Comic Book Guy, and Snake Jailbird.

While there were still some rough edges around "The Simpsons" in Season 3, so many classic elements had been crystallized by this point that it still holds up remarkably well today. The show was also big enough to attract more and more massive celebrities, including the King of Pop himself Michael Jackson in "Stark Raving Dad," voicing a large white mental patient who claimed to be Michael Jackson. "Flaming Moe's" sees Homer fashion a cocktail made of children's cough syrup and fire that Moe takes credit for, turning his tavern into the town's hottest joint. Even Aerosmith does a show there!

Many music icons appeared on "The Simpsons" during this season. Sting appears as himself in "Radio Bart," and even Spinal Tap stops by in "The Otto Show." However, it's not just the celebrity guests that make Season 3 so great, as there are also plenty of great storylines here. Fat Tony makes his first appearance in the terrific "Bart the Murderer," which has Bart joining the local mafia. We're treated to more of Lisa's mature side in "Mr. Lisa Goes to Washington," and Milhouse gets a girlfriend (straining his relationship with Bart) in "Bart's Friend Falls in Love."

By the time Season 4 aired, the cast and crew behind "The Simpsons" had pretty much worked out all of its formative kinks, and thus the show matured into a veritable masterpiece beloved around the world. No conversation about Season 4 would be complete without mentioning "Marge vs. the Monorail," written by Conan O'Brien. The episode had the always-welcome voice of Phil Hartman as Lyle Lanley, a sleazy yet charismatic salesman who tricks Springfield into building a poorly-made monorail. While Springfield's citizens don't always make the best decisions (like constantly voting for Mayor Quimby), nobody could blame them for falling for Lanley's catchy tune, "The Monorail Song." 

"Marge vs. the Monorail" is often seen as a turning point for "The Simpsons" as the series began to adopt wackier and wackier scenarios, which have since become their signature style of humor. "Krusty Gets Kancelled" saw Krusty the Clown's show taken off the air only for him to make a valiant rebound with the help of fellow entertainers Johnny Carson, Luke Perry, Bette Midler, Hugh Hefner, and the Red Hot Chili Peppers (all played by their real-life counterparts). The season also has another fan-favorite episode, "Last Exit to Springfield," which follows Homer as he becomes the head of the nuclear power plant's union in a bid to restore the workers' dental plan so that Lisa can get braces.

At the top of our list we have Season 6, a veritable "greatest hits" of classic "Simpsons" episodes, each filled to capacity with amazing character moments and gags. "Homer the Great" saw Homer accidentally become the leader of the exclusive clandestine club the Stonecutters, whose members leave when Homer tries to steer them in a more altruistic direction. "Lemon of Troy" told the story of how Bart and his friends snuck into nearby Shelbyville to take back Springfield's fabled lemon tree. We even got a glimpse of a possible future in the surprisingly touching "Lisa's Wedding."

One of the more notable episodes of Season 6 was its cliffhanger finale, "Who Shot Mr. Burns? (Part One)." What could've been a sleazy attempt to boost ratings ended up becoming a classic moment in "Simpsons" history. To capitalize on the mystery numerous promotions were held, including the release of "Springfield's Most Wanted," a hilarious sendup of "America's Most Wanted" that even featured the show's host John Walsh. Because "The Simpsons" was so popular at this point, all these promotions did was get fans even more excited for the following season to find out if their theories were true. This season also had a terrific "Treehouse of Horror" installment, which included a hilarious spoof of Stanley Kubrick's "The Shining" titled "The Shinning" (to avoid getting sued, according to Groundskeeper Willie). The episode even featured a one-line cameo from James Earl Jones, voicing Maggie from another dimension.