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11 Episodes of “The Simpsons” That Washingtonians Should Watch During FXX’s Marathon

The best takes on politics, elections, and media in the show's 25-year run.

Image courtesy 20th Century Fox.

As tempting as it might be to cancel all your plans for 12 days and to glue yourself to your couch while indulging in the full run of FXX’s broadcasting of all 552 episodes of The Simpsons and the 2007 feature film, such a feat is both impractical and unhealthy.

Wherever the show’s Springfield truly sits, Washington has been one of The Simpsons’ favorite targets since its 1989 debut. Even as the show has, in the judgment of most fans, declined as it has aged, it still offers consistently smart takes on presidents, members of Congress, elections, and media. Assuming you have to leave the house at some point during the marathon, you should do so judiciously to avoid missing the show’s best indictments of Washington and the episodes that speak most loudly to our region.

Like any roundup of Simpsons episodes, quotes, characters, or anything else connected to the show, this list is by no means a complete index to the series’s best Washington-related moments, but it’s still a perfectly cromulent one.

1. Season 2, Episode 17: “Two Cars in Every Garage and Three Eyes on Every Fish” (Thursday, August 21, at 6 PM)

Charles and David Koch have nothing on C. Montgomery Burns. Two decades before the Supreme Court’s Citizens United ruling unleashed spigots of corporate money into seemingly every election in the country, Springfield Nuclear Power Plant’s diabolical owner attempted to get around environmental laws by running for governor of whatever state The Simpsons is set in. He might have won, too, if not for Marge’s well-timed deployment of Blinky, the three-eyed mutant fish.

2. Season 3, Episode 37: “Mr. Lisa Goes to Washington” (Friday, August 22, at 4 AM)

Long before Lisa Simpson transformed into an eight-year-old atheist and vegan skeptic, she described herself as “fiercely pro-American” in an essay about “American greatness” to win a trip to Washington from a Reader’s Digest-style magazine. True to the episode’s title, the trip is a great riff on Mr. Smith Goes to Washington, ending with Lisa ripping up her original essay in favor of a stem-winding speech indicting members of Congress involved in a bribery scheme to raze a federally protected forest. This early political dip from The Simpsons also gave the series some of its first political backlashes—from the timber industry, which did not like the bribery plot, and from President George H.W. Bush, who took issue with him and his wife, Barbara, being drawn into the episode. In January 1992, four months after the episode first aired, President Bush said in a re-election speech that American families should aspire to be “a lot more like the Waltons and a lot less like the Simpsons.”

3. Season 4, Episode 71: “Marge vs. the Monorail” (Friday, August 22, at 9 PM)

This Conan O’Brien-scripted homage to The Music Man, starring Phil Hartman as seersucker-wearing flimflam man Lyle Lanley, did not have much to do with Washington when it first aired in 1993. But it has plenty of relevance for our city in 2014. Besides having a delightfully memorable song, it’s an expert treatise in poor transit planning, as nearly every resident of Springfield succumbs to the hype of an overdue, overbudget, impractical light-rail system. Sound familiar? DC might not be going the same direction as Ogdenville, North Haverbrook, and Brockway, but if it does, we can’t say The Simpsons didn’t warn us.

4. Season 5, Episode 101: “The Boy Who Knew Too Much” (Saturday, August 23, at noon)

Springfield Mayor “Diamond” Joe Quimby is descended from a long line of Kennedy parodies, but this episode reveals just how deep The Simpsons has been able to mine the United States’ most famous political dynasty, from their accents, sexual appetites, and political ruthlessness. What starts as Bart’s attempt to skip school leads to the hilarious trial of Springfield political scion Freddy Quimby, a brilliant send-up of 12 Angry Men and a stark reminder that it’s tough to defeat a political machine.

5. Season 6, Episode 108: “Sideshow Bob Roberts” (Saturday, August 23, at 3:30 PM)

Quimby’s no saint, but when the alternative is Sideshow Bob, better go with the sleazeball than the homicidal maniac. Kelsey Grammer’s appearances as Sideshow Bob are always a treat, but perhaps no more than this one, in which his mayoral campaign against Quimby becomes a hilarious pastiche of every famous political disaster—from the Willie Horton ad that sank 1988 Democratic presidential nominee Michael Dukakis to Richard Nixon’s sloppy 1960 debate appearance to Watergate itself—with Bob as both mastermind and plumber. The episode also introduces loud, bloated, windy radio talker Birch Barlow, a one-off character who proves that Rush Limbaugh is dangerous and obnoxious in any medium.

6. Season 7, Episode 141: “Two Bad Neighbors” (Sunday, August 24, at 8 AM)

That rivalry between The Simpsons and the Bush family was no joke. The gag of George and Barbara moving to Evergreen Terrace came four years after Poppy dropped his infamous Simpsons insult, but this slapstick coup de grâce was worth the wait, and not just because it contained the revelation that Grover Cleveland spanked Grandpa Simpson on two non-consecutive occasions. Bush today might be more appreciated for his skydiving and colorful taste in socks, but it’s not hard at all to imagine him as the unpleasant and fussy patrician neighbor whose tightly wound mannerisms are a gateway to suburban chaos. Who can blame Homer for preferring to eat nachos with Gerald Ford instead?

7. Season 8, Episode 154: “Treehouse of Horror VII” (Sunday, August 24, at 2:30 PM)

Seven words: “Don’t blame me. I voted for Kodos.”

8. Season 8, Episode 171: “Homer vs. the Eighteenth Amendment” (Sunday, August 24, at 11 PM)

Prohibition was a bad idea when it was added to the real-life Constitution and an even worse experiment when modern-day Springfield tried it out. But this episode also delivers a stern warning that applies today. Excessive moralizing is more dangerous than a little bit of vice. (Though making ducks wear pants isn’t the worst idea.)

9. Season 14, Episode 305: “Mr. Spritz Goes to Washington” (Wednesday, August 27, at 6 PM)

If the political careers of Sonny Bono, Jim Bunning, Heath Shuler, and possibly Clay Aiken prove that anyone with enough fame can overcome a lack of substance to get themselves elected to Congress, what’s so unbelievable about a cartoon clown like Krusty? One of the better entries in The Simpsons’ second decade, it’s just another reminder that Washington will always be flush with craven opportunists who keep getting elected because enough folks like them back home.

10. Season 18, Episode 400: “You Kent Always Say What You Want” (Friday, August 29, at 5:30 PM)

Apologies to the Newseum, but when it comes to fictional news anchors, Ron Burgundy’s got nothing on Kent Brockman. Airing in May 2007, before Fox News Channel went full-tilt, Brockman briefly strays away from his smarmy, pandering act and becomes a real newsman again and folk hero to Lisa. Brockman’s revival ends abruptly when he gets a big raise from his network, which looks and acts a lot like a certain cable news channel known for sharing strategies with the Republican Party.

11. Season 19, Episode 409: “E Pluribus Wiggum” (Saturday, August 30, at midnight)

Why not cast a ballot for Ralph Wiggum? Sure, he’s a dolt, but at least he’s been a good boy. In the larger run of things, it’s not the worst argument we’ve heard from candidates for office.

Staff Writer

Benjamin Freed joined Washingtonian in August 2013 and covers politics, business, and media. He was previously the editor of DCist and has also written for Washington City Paper, the New York Times, the New Republic, Slate, and BuzzFeed. He lives in Adams Morgan.