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"Sideshow Bob Roberts" is the fifth episode of the sixth season of the American animated television series The Simpsons. It originally aired on the Fox network in the United States on October 9, 1994. The episode sees Kelsey Grammer return as Sideshow Bob for his fourth appearance. Clips from previous episodes featuring Bob were used to remind viewers who he was and what he had done. The two Republicans who follow Bob around were based on H. R. Haldeman and John Ehrlichman, two of Richard Nixon's closest advisors during Watergate. Birch Barlow's question to Mayor Quimby about whether his stance on crime would differ if it was his family being attacked is a reference to Bernard Shaw's similar question to Democratic candidate Michael Dukakis during the 1988 presidential debates. Birch Barlow is a parody of American talk show host and political commentator Rush Limbaugh. a choice David Mirkin found "very sad". Archie Comics characters Archie Andrews, Reggie Mantle, Moose Mason and Jughead Jones are shown throwing Homer on the Simpsons' lawn and warning him to "stay out of Riverdale!" The epitaph on The Big Bopper's gravestone is "Gooooodbye, Baby!" a reference to the opening line of his song "Chantilly Lace" – "Hellooo Baby!". Matthew Henry writes in the same book that the episode "well illustrates the battle of [political] ideologies [ ] and its engagement with the politics of sexuality". He refers to the scene where Smithers intimates that Bob rigged the election; his motivation for whistleblowing is Bob's conservative policies, which disagree with his "choice of lifestyle", namely his homosexuality. Henry concludes the scene shows that conservative politics and homosexuality "cannot coexist" and that the scene marks the point where Smithers' sexuality became "public and overtly political". Erik Adams writes that the episode "saves its greatest reserves of comedic contempt for a single entity—but it’s an entity that represents multitudes. The subjects of the episode’s most effective political takedowns aren’t Republicans (though their local headquarters is portrayed as a dreamhouse from the Universal backlot circa Frankenstein) or Democrats (this in spite the fact that Springfield’s resident 'Spendocrat' dynamo, Mayor 'Diamond' Joe Quimby, willingly admits to all questions of his character save for illiteracy—and even that’s a recent development). No, the group that takes it on the chin most vigorously in this, The Simpsons’ finest half hour of political satire, is the American voting public."

In its original broadcast, "Sideshow Bob Roberts" finished tied for 64th place in the weekly ratings for the week of October 3 to October 9, 1994, with a Nielsen rating of 8.6. It was the sixth highest rated show on the Fox network that week. Warren Martyn and Adrian Wood, in I Can't Believe It's a Bigger and Better Updated Unofficial Simpsons Guide, noted the episode was: "A stunningly outspoken political satire that drew considerable disapproval from the Republican Party when it was aired." Thomas Rozwadowski of Green Bay Press Gazette placed the episode among his list of the ten best episodes of the show which have lessons: "Corrupt politicians always get their comeuppance. Or not." He also highlighted Bob's campaign advert and Kent Brockman's line: "And the results are in. For Sideshow Bob, 100 percent. For Joe Quimby, 1 percent. And we remind you, there is a 1 percent margin of error."

The episode has been used in a course at Columbia College Chicago. The course titled "The Simpsons as Satirical Authors" featured "Sideshow Bob Roberts" as one of the episodes screened for the "What's (Not) Wrong with America? Critiquing the U. S. Government" topic. The episode contains the first use of the word "meh" on the show. Writer John Swartzwelder claims credit for introducing the word to the writers. "I originally heard the word from Howie Krakow, my creative director at Hurvis, Binzer & Churchill, in 1970 or 1971," Swartzwelder told The New Yorker in 2021. "He said it was the funniest word in the world. I don’t know when it was invented, or by who, but I got the impression it was already very old when Howie told it to me." The word, which was later included in the Collins English Dictionary, is credited as being popularized by the show, principally following its usage in the season twelve episode "Hungry, Hungry Homer". In "Sideshow Bob Roberts", the word is used by the librarian who provides Lisa with the town's voting records, in response to her questioning their unclassified nature.