A Classic ‘Simpsons’ Episode Tried (and Failed) to Win a Prestigious Literary Award
Bart Simpson’s mortal enemy Sideshow Bob has attempted a number of nefarious schemes over the years — from committing armed robbery in an effort to frame Krusty the Clown, to stealing a nuclear bomb from a military base, to running for public office on the Republican ticket.
But the most grisly Sideshow Bob-centric episode was arguably his second-ever appearance, in Season Three’s “Black Widower.” That’s the one where Bob marries Aunt Selma, then attempts to murder her using a deadly combination of natural gas and MacGyver.
While the episode was written by Jon Vitti, the story was credited to Simpsons co-developer Sam Simon and Thomas Chastain. The second name may not sound familiar to fans, considering that he was only ever credited for this one episode.
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Chastain was a successful mystery writer, and the author of Who Killed the Robins Family?, a novel that tasked readers with solving the unexplained disappearance of the fictional Robinses, with one lucky detective receiving a $10,000 prize for submitting the correct solution. Come to think of it, it was essentially a precursor to the “Who Shot Mr. Burns?” contest.
As then-co-showrunner Mike Reiss revealed in the episode’s DVD commentary, Chastain, who once headed the Mystery Writers of America, was enlisted by Simon to help “construct the mystery,” which explains why the clues were laid out in such a way that audiences could piece together the details of Sideshow Bob’s murder plot, just as Bart did, from Selma’s lack of smell, to her post-MacGyver cigarette, to Sideshow Bob’s conspicuous insistence on staying in a hotel room with a gas fireplace.
“We had our eyes toward winning an Edgar Award,” Reiss revealed, adding, “When you’re in show business, all you think about is, ‘What award can I win?’” The Edgar Awards are the literary honor for achievements in mystery writing, presented by the Mystery Writers of America. They are, of course, named after Edgar Allan Poe, who, it could be argued, was also a Simpsons writer
Reiss wrote about “Black Widower” in his book Springfield Confidential: Jokes, Secrets and Outright Lies from a Lifetime Writing for The Simpsons, and specifically noted that Simon was “hoping to win an Edgar Award.” Reiss pointed out that while The Simpsons failed in its bid to land an Edgar, he later won one for his “caveman detective story” Cro-Magnon, P.I. “The award is a painted plaster bust of Edgar Allan Poe,” Reiss wrote. “It looks like a novelty bottle that should be filled with bourbon, as the real Poe often was.”
Who knows, maybe in one of the next few seasons The Simpsons will finally come up with a mystery worthy of this surprisingly non-alcoholic award.
