Random Best Seasons of 'The Simpsons' (32 items)

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  (#1) The Simpsons season 6

  • The Simpsons

  The sixth season of The Simpsons premiered on September 4, 1994 and contains 25 episodes. This season finds the residents of Springfield trying to uncover who shot Mr. Burns.

  This season features several unforgettable episodes including: "Lisa's Rival," "Itchy & Scratchy Land," and "The Springfield Connection."

  Memorable moments from Season 6 include:

  • Bleeding Gums Murphy dies.
  • Homer goes to clown college.
  • Homer becomes a Stonecutter.
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  (#2) The Simpsons season 5

  • The Simpsons

  The fifth season of The Simpsons premiered on September 20, 1993 and contains 22 episodes. This season contains the series' hundredth episode.

  This season features several unforgettable episodes including: "Cape Feare," "Boy-Scoutz 'N the Hood," and "Bart Gets an Elephant."

  Memorable moments from Season 5 include:

  • The Simpsons do an almost shot for shot remake of Scorsese's Cape Fear.
  • Homer joins barbershop quartet, The Be Sharps. 
  • Homer goes to space.
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  (#3) The Simpsons season 4

  • The Simpsons

  The fourth season of The Simpsons premiered on September 24, 1992 and contains 22 episodes. This season further develops other Springfield characters like Krusty the Clown and Ralph Wiggum. 

  This season features several unforgettable episodes including: "A Streetcar Named Marge," "Mr. Plow," and "Whacking Day."

  Memorable moments from Season 4 include:

  • Homer suffers a heart attack.
  • Lisa "Cho-Cho-Chooses" Ralph.
  • Krusty's show gets canceled.
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  (#4) The Simpsons season 3

  • The Simpsons

  The third season of The Simpsons premiered on September 19, 1991 and contains 24 episodes. This season won six Emmy Awards.

  This season features several unforgettable episodes including" "Stark Raving Dad," "I Married Marge," and "Colonel Homer."

  Memorable moments from Season 3 include:

  • Homer gets committed to a mental hospital.
  • Flanders opens the Leftorium.
  • Moe steals the recipe for the Flaming Homer.
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  (#5) The Simpsons season 7

  • The Simpsons

  The seventh season of The Simpsons premiered on September 17, 1995 and contains 25 episodes. This season has many notable cameos like Sir Paul McCartney and Billy Corgan from The Smashing Pumpkins.

  This season features several unforgettable episodes including: "Radioactive Man," "Lisa the Vegetarian," and "22 Short Films About Springfield."

  Memorable moments from Season 7 include:

  • George Bush moves to Springfield.
  • Selma marries Troy McClure.
  • Homer joins Hullabalooza.
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  (#6) The Simpsons season 8

  • The Simpsons

  The eighth season of The Simpsons premiered on October 27, 1996 and contains 25 episodes. This season finds Milhouse's parents getting a divorce.

  This season features several unforgettable episodes including: "You Only Move Twice," "The Springfield Files," and "The Secret War of Lisa Simpson."

  Memorable moments from Season 8 include:

  • Bart works at a burlesque saloon.
  • Homer voices Poochie.
  • Santos L. Halper gets a credit card.
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  (#7) The Simpsons season 2

  • The Simpsons

  The second season of The Simpsons premiered on October 11, 1990 and contains 22 episodes. This season featured the very first "Treehouse of Horror" installment.

  This season contains several unforgettable episodes including: "Bart Gets an 'F,'" "Homer vs. Lisa and the 8th Commandment," and "Blood Feud."

  Memorable moments from Season 2 include:

  • Bart catches a three-eyed fish.
  • Marge campaigns against "The Itchy & Scratchy Show".
  • Homer meets his half-brother Herb.
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  (#8) The Simpsons season 10

  • The Simpsons

  The tenth season of The Simpsons premiered on August 23, 1998 and contains 23 episodes. This season includes the final guest appearance by Phil Hartman.

  This season features several unforgettable episodes including: "Lard of the Dance," "Mayored to the Mob," and "Mom and Pop Art."

  Memorable moments from Season 10 include:

  • Kim Basinger and Alec Baldwin hire Homer as their personal assistant.
  • Homer becomes a hippie.
  • Lisa joins Mensa.
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  (#9) The Simpsons season 9

  • The Simpsons

  The ninth season of The Simpsons premiered on September 21, 1997 and contains 25 episodes. This season finds Homer and Marge rekindling their love for each other.

  This season features several unforgettable episodes including: "Lisa's Sax," "Bart Carny," and "The Last Temptation of Krust."

  Memorable moments from Season 9 include:

  • Bart and Ralph go on a play date.
  • Homer tries to climb the Murderhorn.
  • The Simpsons become Movementarians.
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  (#10) The Simpsons season 12

  • The Simpsons

  The twelfth season of The Simpsons premiered on November 1, 2000 and contains 21 episodes. This season finds Flanders looking for ways to keep Maude in his life.

  This season features several unforgettable episodes including: "Skinner's Sense of Snow," "Day of the Jackanapes," and "Bye, Bye, Nerdie."

  Memorable moments from Season 12 include:

  • Homer and Bart start grifting.
  • Bart and Milhouse fill in for Comic Book Guy.
  • Bart, Nelson, Milhouse and Ralph become a boy band.
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  (#11) The Simpsons season 1

  • The Simpsons

  The first season of The Simpsons premiered on December 17, 1989 and contains 13 episodes. This season introduces viewers to The Simpson family and their friends.

  This season features several unforgettable episodes including: "Simpsons Roasting on an Open Fire," "The Telltale Head" and "Some Enchanted Evening."

  Memorable moments from Season 1 include:

  • The Simpsons go to a company picnic.
  • Homer is suspected of being Bigfoot.
  • Bart goes to France.
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  (#12) The Simpsons season 15

  • The Simpsons

  The fifteenth season of The Simpsons premiered on November 2, 2003 and contains 22 episodes. This season welcomes the brief return of Homer's mother.

  This season features several unforgettable episodes including: "The Fat and the Furriest," "Marge vs. Singles, Seniors, Childless Couples and Teens and Gays," and "Co-Dependents' Day."

  Memorable moments from Season 15 include:

  • Homer becomes Pie Man.
  • Homer becomes a robot.
  • Homer becomes the nicest guy in Springfield.
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  (#13) The Simpsons season 13

  • The Simpsons

  The thirteenth season of The Simpsons premiered on November 6, 2001 and contains 22 episodes. This season finds Springfield being named the, "World's Fattest Town".

  This season features several unforgettable episodes including: "Homer the Moe," "Jaws Wired Shut" and "The Lastest Gun in the West."

  Memorable moments from Season 13 include:

  • Homer gets roasted.
  • Bart's comic "Angry Dad" becomes a hit.
  • Homer becomes a cop.
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  (#14) The Simpsons season 11

  • The Simpsons

  The eleventh season of The Simpsons premiered on September. 26, 1999 and contains 22 episodes. This season found the residents of Springfield dealing with the passing of one of their neighbors.

  This season features several unforgettable episodes including: "Guess Who's Coming to Criticize Dinner," "E-I-E-I-(Annoyed Grunt)," and "Alone Again, Natura-diddily."

  Memorable moments from Season 11 include:

  • Homer grows tomacco.
  • Manjula gives birth to octuplets.
  • Maude Flanders dies.
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  (#15) The Simpsons season 14

  • The Simpsons

  The fourteenth season of The Simpsons premiered on November 3, 2002 and contains 22 episodes. This season includes the series' 300th episode.

  This season features several unforgettable episodes including: "How I Spent My Strummer Vacation," "A Star Is Born-Again," and "Moe Baby Blues."

  Memorable moments from Season 14 include:

  • Santa's Little Helper becomes the mascot for Duff beer.
  • Moe saves Maggie's life.
  • Marge hits Homer with a car.
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  (#16) The Simpsons season 17

  • The Simpsons

  The seventeenth season of The Simpsons premiered on September 11, 2005 and contains 22 episodes. Kelsey Grammer won an Emmy Award for voicing Sideshow Bob during this season.

  This season features several unforgettable episodes including: "The Bonfire of the Manatees," "Homer's Paternity Coot," and "Homer Simpson, This Is Your Wife."

  Memorable moments from Season 17 include:

  • Homer hosts a "pox party".
  • Bart becomes a mama's boy.
  • Grandpa becomes a bullfighter.
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  (#17) The Simpsons - Season 20

  • The Simpsons

  The twentieth season of The Simpsons premiered on September 28, 2008 and contains 21 episodes. This season found the primary voice actors getting a raise to $400,000 per episode.

  This season features several unforgettable episodes including: "Sex, Pies, and Idiot Scrapes," "Homer and Lisa Exchange Cross Words," and "Waverly Hills, 9-0-2-1-D'oh."

  Memorable moments from Season 20 include:

  • Lisa takes anti-depressants.
  • Marge and Homer get re-married.
  • Homer becomes a bounty hunter.
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  (#18) The Simpsons season 19

  • The Simpsons

  The nineteenth season of The Simpsons premiered on September 23, 2007 and contains 20 episodes. This season features the return of Sideshow Bob and his brother Cecil Terwilliger.

  This season features several unforgettable episodes including: "He Loves to Fly and He D'ohs," "Husbands and Knives," and "All About Lisa."

  Memorable moments from Season 19 include:

  • The Simpsons go to Sundance.
  • Homer saves Mr. Burns from drowning.
  • Lurleen Lumpkin returns to Springfield.
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  (#19) The Simpsons - Season 27

  The twenty-seventh season The Simpsons premiered on September 27, 2015 and contains 22 episodes. This was the final season to credit Sam Simon as a producer due to his passing in 2015.

  This season features several unforgettable episodes including: "Barthood", "Halloween of Horror", and "Orange Is the New Yellow."

   Memorable moments from Season 27 include:

  • The story of Bart's life, spanning from six years old to adulthood, is told.
  • We see the first Halloween-themed episode of The Simpsons to be fully canon and not a part of the Treehouse of Horror series.
  • Marge gets arrested after Bart goes to the park unsupervised.
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  (#20) The Simpsons season 16

  • The Simpsons

  The sixteenth season of The Simpsons premiered on November 7, 2004 and contains 21 episodes. This season further explores the dysfunction of the Simpson family.

  This season features several unforgettable episodes including: "Sleeping with the Enemy," "Homer and Ned's Hail Mary Pass," and "Thank God It's Doomsday."

  Memorable moments from Season 16 include:

  • Homer and Bart consider Catholicism.
  • Homer makes a new friend.
  • Marge becomes a surrogate mother to Nelson.
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  (#21) The Simpsons season 18

  • The Simpsons

  The eighteenth season of The Simpsons premiered on September 10, 2006 and contains 22 episodes. This season marks the 20th anniversary of The Simpsons' franchise.

  This season features several unforgettable episodes including: "The Mook, the Chef, the Wife and Her Homer," "Moe'N'a Lisa," and "Stop, or My Dog Will Shoot."

  Memorable moments from Season 18 include:

  • Homer becomes a member of the paparazzi.
  • Bart gets engaged.
  • The Simpsons befriend the mob.
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  (#22) The Simpsons - Season 26

  • The Simpsons

  The twenty-sixth season of The Simpsons premiered on September 28, 2014 and contains 20 episodes. This season features the return of Sideshow Bob and his brother Cecil Terwilliger.

   This season features several unforgettable episodes including: "Simpsorama", "Bart's New Friend", and "My Fare Lady"

   Memorable moments from Season 26 include:

  • Crossover with Futurama
  • Homer goes to a hypnotist and ends up believing he is ten years old.
  • Marge becomes a chauffeur.
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  (#23) The Simpsons - Season 28

  The twenty-eighth season The Simpsons premiered on September 25, 2016 and contains 22 episodes. This season features the very first hour-long episode.

  This season features several unforgettable episodes including: "The Great Phatsby," "Looking for Mr. Goodbart," and "Treehouse of Horror XXVII."

   Memorable moments from Season 28 include:

  • Mr. Burns hires a pretend family.
  • Homer and Kirk coach lacrosse.
  • Mr. Burns starts a university.
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  (#24) The Simpsons Season 21

  • The Simpsons

  The twenty-first season of The Simpsons premiered on September 27, 2009 and contains 23 episodes. This season found the series becoming the longest-running American primetime television series.

  This season features several unforgettable episodes including: "Homer the Whopper," "The Devil Wears Nada," and "Moe Letter Blues."

  Memorable moments from Season 21 include:

  • Bart gets mentored by a veteran prankster.
  • Homer becomes Everyman.
  • The Simpsons and Flanders go to Jerusalem.
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  (#25) The Simpsons - Season 22

  • The Simpsons

  The twenty-second season of The Simpsons premiered on September 26, 2010 and contains 22 episodes. This season finds The Simpsons exploring the full range of their individual talents.

  This season features several unforgettable episodes including: "Elementary School Musical," "The Fight Before Christmas," and "A Midsummer's Nice Dream."

  Memorable moments from Season 22 include:

  • Bart becomes a bully.
  • Moe's Tavern becomes a gay bar.
  • Fat Tony and Selma get married.
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  (#26) The Simpsons - Season 25

  • The Simpsons

  The twenty-fifth season of The Simpsons premiered on September 29, 2013 and contains 22 episodes. This season, Harry Shearer won an Emmy Award for his voice-over work.

  This season features several unforgettable episodes including: "Homerland," "The Kid Is All Right," and "Days of Future Future."

  Memorable moments from Season 25 include:

  • Homer regrets selling his Mapple stock.
  • Milhouse gets bitten by a zombie.
  • Homer goes to Lego world.
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  (#27) The Simpsons - Season 23

  • The Simpsons

  The twenty-third season of The Simpsons premiered on September 25, 2011 and contains 22 episodes. This season contains the series' 500th episode.

  This season features several unforgettable episodes including: "The Falcon and the D'ohman," "The Man in the Blue Flannel Pants," and "The Spy Who Learned Me."

  Memorable moments from Season 23 include:

  • Lisa gets help from Lady Gaga.
  • Ned Flanders and Edna Krabappel elope.
  • Homer becomes a political pundit.
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  (#28) The Simpsons - Season 24

  • The Simpsons

  The twenty-fourth season of The Simpsons premiered on September 30, 2012 and contains 22 episodes. This season continues to follow the residents of Springfield as the get involved in crazy situations.

  This season features several unforgettable episodes including: "Adventures in Baby-Getting," "A Test Before Trying," and "Whiskey Business."

  Memorable moments from Season 24 include:

  • Grandpa moves in with Homer and his family.
  • Bart gives Milhouse a haircut.
  • Homer gets inspired by 50 Shades of Grey.
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  (#29) The Simpsons - Season 29

  The twenty-ninth season of The Simpsons premiered on October 1, 2017 and contains 21 episodes. This season finds the series setting the record for the longest-running scripted series in primetime television.

  This season features several unforgettable episodes including: "Springfield Splendor," "Mr. Lisa's Opus," and "Left Behind."

  Memorable moments from Season 29 include:

  • Marge and Lisa create a graphic novel.
  • Grampa gets hearing aids.
  • Krusty goes dramatic.
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  (#30) The Simpsons - Season 30

  The thirtieth season of The Simpsons premiered on September 30, 2018 and contains 23 episodes. This season finds Al Jean returning as the showrunner.

  This season features several unforgettable episodes including: "Bart's Not Dead," "Krusty the Clown," and "D'oh Canada."

  Memorable moments from Season 30 include:

  • Lisa's college fund gets stolen.
  • The Simpsons visit Niagara Falls.
  • Self-driving cars come to Springfield.

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