‘Sideshow’ Bob Underdunk Tewilliger is the best kind of villain, in the Dr. Doom mold: erudite, cultured, and intelligent; the kind of guy who could be a bestselling author, famed classical actor or renowned university professor, if not for the fact that he’s a homicidal maniac.
Despite (or, perhaps, because of) his sophistication and high class pedigree, Bob was forced to endure physical gag after physical gag as Krusty’s sidekick, forced to remain silent, communicating only via slide whistle.
His career as a frustrated criminal mastermind began when he framed Krusty the Clown and took control of Krusty’s show, transforming it into a kind of “Masterpiece Theatre” for children. Exposed by Bart, this led in turn to Bob’s psychotic obsession with killing Bart Simpson in revenge. From there, Bob engaged in scheme after scheme, only to have each foiled in turn by Bart (and, to a lesser extent, Lisa). He married Aunt Selma (planning to kill her for the money), ran for mayor, set off an atomic weapon, and tried to kill Bart, a lot, all the while humming a Gilbert and Sullivan tune or spouting off Shakespearean quotations.
Favorite Sideshow Bob episode: I have three: season five’s Cape Feare, when Bob’s desire for revenge forces the family to enter witness protection, season six’s Sideshow Bob Roberts, in which Bob runs for Mayor, and season eight’s Brother from Another Series, where Bob claims to have reformed and helps his brother Cecil build a hydroelectric dam under the suspicious eyes of Bart and Lisa (I wish the ending of this episode had stuck, with Bob legitimately reformed and over his obsession with Bart but imprisoned alongside his criminal brother nonetheless. I was disappointed when Bob had seemingly returned to his murderous ways in his next appearance. But I digress).
Amongst those three, the favorite is easily Cape Feare. I remember the first time I saw the rake sequence (in which Bob, tracking the Simpsons to their new home, inexplicably finds himself surrounded by rakes, all turned so they slap him in the face as he takes a step) it caused one of the hardest and longest laughs of my entire life. If I had to pick a favorite overall episode, that one would definitely be in the running. But that’s another post.
Favorite Sideshow Bob lines: You want the truth! You can't handle the truth! No truth handler you! Bah! I deride your truth handling abilities!
Well, if it isn't my arch-nemesis Bart Simpson. And his sister Lisa to whom I'm fairly indifferent.
No children have ever meddled with the Republican Party and lived to tell about it.
Your guilty consciences may force you to vote Democratic, but deep in your hearts you long for a cold, Republican leader who'll cut taxes, brutalize criminals, and rule you like a king!
"Attempted murder?" Now really, what is that? Do they give a Nobel Prize for attempted chemistry?