Sideshow Bob Roberts - Production

Production

Although the episode primarily mocks the Republican Party, the writers included several jokes at the expense of the Democratic Party, liberal and conservative politics, to try to be as neutral as possible. Writers Bill Oakley and Josh Weinstein were very interested in the Watergate scandal and based a lot of the second act on that. Mark Kirkland directed the episode.

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. Bob's Cape Fear musical cue from the episode "Cape Feare" is also reused. Showrunner David Mirkin found directing Grammer "a joy". Dr. Demento also guest-starred, as did Larry King for the second time, while Henry Corden voices Fred Flintstone. One of the prisoners in Bob's campaign advert is a caricature of producer Richard Sakai. The "Les Wynan" joke was pitched by Mike Reiss. The episode does not feature a chalkboard or couch gag, cutting straight from the clouds to the TV. Some syndication edits have included a couch gag.

The episode contains the first usage of the word "meh" in the show. 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.

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