When you think of The Simpsons villains, a few faces come to mind: Mr. Burns, the greedy nuclear baron; Fat Tony, the gentleman gangster; and then, towering above them all at six-foot-six— Sideshow Bob .
Let’s break down the fraternal feud (and partnership) of Springfield’s most articulate sociopaths. Sideshow Bob (Kelsey Grammer) started as Krusty the Clown’s sidekick. Framing Krusty for robbery, marrying Selma for her money, trying to kill Bart via electrocution—Bob’s modus operandi is theatrical, vengeful, and increasingly unhinged. His fatal flaw? A monstrous ego and a pathological need to monologue. sideshow bob and cecil
In their subsequent appearance ( Funeral for a Fiend , Season 19), the brothers finally team up. Their plot? To fake Bob’s death at his own funeral to lure the Simpsons into a trap. It fails spectacularly, not because the Simpsons are smart, but because the Terwilliger brothers cannot stop trying to out-intellectualize and betray each other. When you think of The Simpsons villains, a
But as Captain McAllister says: “She’s built like a steakhouse, but she handles like a bistro.” You know the other shoe is going to drop. The brilliance of Brother from Another Series is that it plays with our expectations. For 90% of the episode, we think Cecil is the good brother. Bob is fresh out of prison, trying to prove he’s reformed, while Cecil shows him up as the family success. Sideshow Bob (Kelsey Grammer) started as Krusty the