5. Sideshow Bob is what would've happened to the show's creators had they failed: the bitterness of the idealist in defeat.
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Replying to @HeerJeet
6. Sideshow Bob raises a fundamental question: what is the role of the cultural elitist in a mass democracy?
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Replying to @HeerJeet
7. One answer is that the cultural elitist should simply turn his nose at the masses & become snob: the route of Mencken, Vidal, etc.
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Replying to @HeerJeet
8. The nobility of Sideshow Bob is he doesn't take the easy (and lazy) path of snobbery but sees it as his mission to uplift the masses.
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Replying to @HeerJeet
9. For the elitist to uplift the masses means entering into a complex love/hate relationship with them: which is what Bob has with Bart.
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Replying to @HeerJeet
10. Sideshow Bob wants to destroy Bart but also edify him: "to send Bart to heaven before he sent him to hell."
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Replying to @HeerJeet
11. The love/hate feelings Sideshow Bob has for Bart are surely shared on some level by the show's writers: Bart is their paycheck & a pain
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Replying to @HeerJeet
12. Sideshow Bob embodies something rarely celebrated in our culture: the creative power of negativity: scorn as life-affirmation.
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Replying to @HeerJeet
13. Stephen Marche interestingly noted that Sideshow Bob is a rare character in show who points to values outside Springfieldian mainstream.
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Replying to @HeerJeet
14. Sideshow Bob recommends "the Springfield Review of Books. Just look at these amusing pictures of Susan Sontag and Gore Vidal."
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15. The other character who points outside of Springfieldian values is Lisa: not so much as she is as a girl but as she will be as a woman.
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Replying to @HeerJeet
16. Lisa of course is more complex character. We can imagine her growing out of Springfield, seeing its flaws, but flinching from hating it.
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Replying to @HeerJeet
17. In conclusion: Sideshow Bob is great character because he speaks to way Simpsons as a show is reflectively aware of its place in culture
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