The 10 Best Simpsons Episodes of All Time... So Far

The Simpsons will reach the 500-episode mark this Sunday, a feat unmatched by any other sitcom (animated or not). There have been many guest stars over the last 23 seasons and the 500th episode, "At Long Last Leave," will be no exception: The show will welcome WikiLeaks founder Julian Assange to Springfield. In true Assange fashion, his lines were recorded over a secret phone line while he was under house arrest, presumably hidden deep inside the Earth’s core (citation needed). It's yet to be determined whether or not Episode 500 will go down in the books as one of the show's best, but considering the magnitude of the series thus far, we thought now would be a good time to reflect on a few of the existing 499 episodes that will be hard to top. Here are 10 of the best episodes of The Simpsons, evvv-er.

#10: "Homie the Clown" (S06E15)

To pay off gambling debts to the mafia, Krusty opens a clown college to expand his brand. Of course, Homer enrolls in the course and becomes a regional Krusty. As he is about to quit his newest dream, he realizes the perks of being the most famous clown in Springfield and takes advantage of everything Krusty has coming to him, including a mafia hit. This episode has one of my favorite endings to a Simpsons episode, ever.

#9: "Lisa the Iconoclast" (S07E16)

While researching an essay for Springfield’s bicentennial celebration, Lisa finds out that town founder Jebediah Springfield was actually a fiendish pirate named Hans Sprungfeld, who had a tongue made of silver. In trying to expose the truth, Lisa becomes an outcast in her own town and is even banned from the historical society for three months by Hollis Hurlbut, the curator (voiced by Donald Sutherland). This episode gave us two great new words: "cromulent" and "embiggen."

#8: "You Only Move Twice" (S08E02)

Homer is offered a new high-paying job for the Globex Corporation, which is owned by Hank Scorpio, and moves the whole family to Cypress Creek. But the Simpsons' new life turns out to be not as great as they thought it would be: Marge has nothing to do around the house, Bart is sent to remedial class, and Lisa is allergic to everything. Oh, and Homer is oblivious to the fact that Hank Scorpio is an awesome super villain.

#7: "Marge vs. the Monorail" (S04E12)

For once, the citizens of Springfield agree with Marge on something and decide to use their recently acquired $3 million to fix up Main Street and build a monorail. That is, until the silver-tongued (figuratively, not literally like Jebidiah Springfield) Lyle Lanley sways public opinion through song. The monorail is a scam and puts everyone on board in mortal peril. Luckily Leonard Nimoy is on hand to save the day.

#6: "Bart Gets Famous" (S05E12)

After a thrilling trip to the box factory, Bart stumbles his way into a job as Krusty’s assistant. A chance walk-on role lands Bart in the spotlight when his accidental catchphrase, “I didn’t do it,” takes off. Bart learns that celebrity isn’t all it’s cracked up to be when he's pigeonholed as the “I didn’t do it” boy. The show pokes fun at itself by having all the characters utter their own famous catchphrases, one after another.

#5: "Homer at the Bat" (S03E17)

After Homer leads the Nuclear Power Plant softball team to the championship against Shelbyville, Mr. Burns decides to call in some ringers to pad his roster. Mr. Burns’ dream team turns out to be impossible to assemble, as most of the players he suggests are no longer alive. He gets all the best Major League Baseball players of 1992 to replace the ones who got the team to the championship.

#4: "Last Exit to Springfield" (S04E17)

“Dental plan. Lisa needs braces.” That quote pretty much sums up this entire episode. Homer is appointed president of the union at the power plant and goes up against Mr. Burns in order to keep their company dental plan in tact.

#3: "A Fish Called Selma" (S07E19)

Troy McClure needs to get his career back on track and dispel rumors of his strange sexual escapades involving fish. To escape said rumors, he gets involved with Selma Bouvier and his career picks up again. This inspires him to marry her, and after McClure stars in the Broadway musical version of Planet of the Apes, he's up for the role of McBain’s sidekick in the new McBain movie. The sham doesn’t last forever, though, and eventually McClure decides to star in The Contrabulous Fabtraption of Professor Horatio Hufnagel.

#2: "Burns, Baby Burns" (S08E04)

After attending the annual Harvard vs. Yale football game, Mr. Burns is spotted by his long-lost son, Larry (voiced by Rodney Dangerfield). Larry hitchhikes his way to Springfield and is picked up by the Simpsons, who are on their way home from a fascinating trip to the cider mill. Larry finds that he has much more in common with Homer than he does with his father and the two stage a fake kidnapping to win Mr. Burns’ love.

#1: "The Itchy & Scratchy & Poochie Show" (S08E14)

Producer Roger Meyers, Jr. makes a hasty decision to add a one-dimensional character, Poochie, to The Itchy & Scratchy Show in order to give declining ratings a shot in the arm. After a lengthy audition process that includes Troy McClure and Otto, Homer is cast as Poochie’s voice. After a huge marketing push, the Poochie experiment is a huge failure and The Itchy & Scratchy Show’s ratings tank even further.

Did your favorite Simpsons episode make this list, or do you have more to add? Will you be tuning in for Episode 500 on Sunday?

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