‘Simpsons’ Did It

‘The Simpsons’ Predicted Trump's Mob

Simpsons writer Bill Oakley spills on unknowingly creating Trump 2016 in the form of Sideshow Bob 1994.

11.29.15 5:01 AM ET

Early in “Sideshow Bob Roberts,” an episode of The Simpsons that begins with its murderous title character incarcerated, a Rush Limbaugh clone named Birch Barlow calls his audience to action.

“My friends, Bob is a political prisoner,” says the animated radio host, whose voice Harry Shearer provides with the same gassy verve of the fictional bloviator’s real-life inspiration. “I want every loyal listener to do everything they can to get him out of jail.”

Moe the bartender immediately responds with, “All right, you heard the man.” He then passes out grenades to his regulars.

The men only disarm when Barney drunkenly blurts out: “I think he meant through nonviolent, grassroots political action.”

A scene featuring an angry demagogue spewing overheated rhetoric to an impressionable mob of cartoon characters may feel kind of on the nose in 2015, but that’s the point. Since “Sideshow Bob Roberts” aired on Oct. 9, 1994, American political discourse has become intolerable in ways that render satire almost needless. 

“The masses now behave a little bit more like the population of Springfield than they did back then,” co-writer Bill Oakley told The Daily Beast.

The classic episode, which pits felonious Republican Sideshow Bob against inevitable incumbent Democrat Joe Quimby in the town’s mayoral race, lampoons 20th-century politics. It also inadvertently captures the absurdity of the modern political climate. 

Oakley does want to make this clear, however: “The political discourse now is way more fucked up than the one depicted in the show.”

While growing up in Washington, D.C., in the ’70s and ’80s, both Oakley and his writing partner Josh Weinstein became Watergate obsessives. After joining the staff of The Simpsons in the early ’90s, they naturally came up with a political parody centered on Sideshow Bob. Brilliantly voiced by Kelsey Grammer, the big-haired psychopath already had appeared in a handful of episodes. By the sixth season of the show, he’d framed Krusty the Klown for murder, tried to blow up Marge’s sister Selma, and attempted to kill nemesis Bart.

“Rather than have him be homicidal,” Oakley said, he and Weinstein decided to have Sideshow Bob run for office. But first they needed to bust him out of jail. 

To do that, they created Barlow, who’s introduced as “Springfield's favorite conservative and author of the well-selling book, Only Turkeys Have Left Wings.” His biggest fan is Homer. “It just seems like the kind of thing that he would love,” Oakley said. 

The manipulative, Yale-educated Sideshow Bob soon starts calling in to Barlow’s show from prison. “Kudos for bringing the public back to the Republican Party. It's high time people realized we conservatives aren't all Johnny Hatemongers, Charlie Bible Thumps, or even—God forbid—George Bushes,” he says. 

Barlow quickly proclaims that Bob has been “railroaded by our liberal justice system” and vows to set him free. Springfield rallies around the cause, and Kennedy amalgamation Mayor Quimby, who’s in the middle of a re-election campaign, responds to the groundswell of support for Bob by pardoning him. 

In an early draft of the episode, there actually was a George Stephanopoulos-like, Phil Hartman-voiced campaign manager who advises the shameless Quimby to acquiesce to the public.

“Sir, that mob is very insistent,” he says, “and as you know, we rely quite heavily on the mob vote.” (The character, along with subplots about Lisa working on the Quimby campaign and a failed Republican candidate/Barlow target named Gaylord Packman, were abandoned.) 

After Bob leaves prison, Springfield’s Republican Party—which counts Barlow, Mr. Burns, Rainier Wolfcastle, and a literal blood-drinking monster as its members—decides to install Sideshow Bob as its mayoral candidate.

The writers had fun dropping historical references into the ensuing campaign. They gave Bob two silent henchmen who look suspiciously like Watergate helpers John Ehrlichman and H.R. Haldeman. At the mayoral debate, Quimby is so hopped up on “extra-drowsy formula” flu medicine that he looks as sweaty and disheveled as Richard Nixon did when he faced off against John F. Kennedy in 1960. There are nods to debate moderator Bernard Shaw’s infamous death penalty question to Michael Dukakis in 1988, there’s a re-creation of the Willie Horton attack ad, and there’s this:   

Before you tell the writers to go back to Massachusetts and call them pinkos, like Homer does, it should be noted that The Simpsons makes no effort to hide its political leanings. “The show is unabashedly liberal,” Oakley said. “I think it’s super clear.”

For something as incisive as “Sideshow Bob Roberts” to work, it can’t be objective. “There was no point in being even-handed,” Oakley said.

But that doesn’t mean that the Democrats are sacred cows. At the beginning of the episode, Carl quips, “That Barlow’s a right-wing crackpot. He said Ted Kennedy lacked integrity!” Mayor Quimby, who Dan Castellaneta voices with an exaggerated Hyannis Port accent, is an unintelligent, corrupt philanderer.

“I think it was clear that we gave it to both sides,” Oakley said, “but in different ways.” Not that the show’s ethos seemed to alienate its fans.

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Devotion to The Simpsons cuts across party lines. The show, said Chris Turner, author of Planet Simpson, is “the universal satirical language.” The National Review’s Jonah Goldberg adores it. So does former Ronald Reagan speechwriter Peggy Noonan, who in a 1997 Good Housekeeping column correctly deemed the series “the best family values show on television.” Republican presidential Ted Cruz also is a Simpsons buff, even if his love is unrequited.

“To paraphrase Kang, ‘Ted Cruz?’ Go ahead, throw your vote away,” showrunner Al Jean recently told The Daily Beast when asked about the Texas senator. 


In “Sideshow Bob Roberts,” the citizens of Springfield appear to throw their votes away by electing the man born Robert Underdunk Terwilliger. (“Hmm...I don't agree with his Bart-killing policy, but I do approve of his Selma-killing policy,” Homer says to himself at the voting booth.)

Sensing that Bob’s landslide victory was odd, Bart and Lisa investigate. The episode’s final act is Oakley and Weinstein’s ode to All the President’s Men. Inside Springfield’s Hall of Records, the siblings sift through documents like they’re Woodward and Bernstein at the Library of Congress. The overhead shot of Bart and Lisa, borrowed from the movie, is one of Oakley’s favorite Simpsons moments.

Mr. Burns’ assistant Waylon Smithers serves as their Deep Throat, alerting them to election fraud. His reason for going behind his boss’s back is pretty obvious: “Bob’s ultra-conservative views, err,” he says, “conflict with my…choice of lifestyle.”

Lisa eventually deduces that Sideshow Bob used votes cast by dead people to prevail. During the resulting trial, Bart and Lisa goad him into revealing that he concocted the scheme.

“You need me, Springfield,” he says before getting arrested. “Your guilty conscience may force you to vote Democratic, but deep down inside you secretly long for a cold-hearted Republican to lower taxes, brutalize criminals, and rule you like a king. That’s why I did this: to protect you from yourselves.”

His final speech sounds like something that all but one Republican candidate would think, but never say.

After all, like Sideshow Bob, Donald Trump is a caricature.

This is why Oakley thinks it would be hard for Weinstein and him to write a Simpsons episode that sends up today’s political world. “It’s certainly hard to make it any more outrageous than real life,” he said. But if he were to give it a shot, he’d fall back on the same stereotypes people have been using for a century: Democrats are lazy and incompetent. Republicans are rich and evil.

“The nature of the universe is that there can’t really be any competent public officials of any political party,” Oakley said, “or there would not be any comedy.”