The Simpsons Season 36 Forces The Family To Vacation With Their Greatest Villain

Sideshow Bob first appeared on "The Simpsons" in the episode "The Telltale Head" (February 25, 1990), merely as a background character on "The Krusty the Clown Show." That episode was significant, as it was also the first appearance of Krusty the Clown (Dan Castellaneta), Reverend Lovejoy (Harry Shearer), the bullies Dolph, Jimbo, and Kearny (Tress MacNeille, Tress MacNeille, and Nancy Cartwright), and Apu (Hank Azaria). 

Only a few episodes later, however, Sideshow Bob (Kelsey Grammer) would star in "Krusty Gets Busted" (April 29, 1990), an episode that saw the TV sidekick framing his clown employer, Krusty, for armed robbery. It seems that Bob, a professionally trained actor, resented having to play second-fiddle to an ungrateful star, and wanted revenge. Ultimately, it was Bart (Cartwright) who figured out Bob's scheme and who exonerated Krusty. Bob began hating Bart and began plotting revenge from prison. 

The palm tree-haired actor returned in "Black Widower" (April 9, 1992), wherein he tries to marry and exploit Bart's aunt Selma (Julie Kavner), although he wouldn't really rise to supervillain status until "Cape Feare" (October 7, 1993) wherein he was released from prison, and aimed to murder Bart once and for all, even stalking the family as they undergo witness protective services. Bob has since appeared in over a dozen "Simpsons" episodes, each time expressing his villainous rage, and his evil plots to kill Bart or undo a vital institution. 

And, as it has now been revealed in a special sneak preview in Entertainment Weekly, Bob will return again, this time within a winking spoof of "The White Lotus." It seems that the Simpsons and Bob will find themselves staying at the same swanky resort ... with Bob possessing the upper hand. Thanks to a deal with the devil, the Simpsons will have to share space with their most hated enemy. 

In the above clip, we observe that the Simpsons haven't merely gone to a swanky White Lotus-like resort, but appear to be squatting there for free. When Marge (Kavner) suggests they leave, Homer (Castellaneta) whines that Bob's crimes only go so far as attempted murder. Bob, staying in the suite next door, catches them red-handed. Bart accuses Bob of being a villain, but he claims to have gone straight, having invented a rake that, when stepped on, doesn't thwack you in the face. This is in reference to a joke in "Cape Feare," wherein Bob, dazed after riding on the underside of a car for many miles, staggers to his feet only to step on a rake. A wide shot reveals, somewhat surreally, that Bob is surrounded by many rakes, and he will likely step on them in perpetuity. 

Of course, Bob's shortened rake doesn't quite solve the problem, however. It doesn't thwack him in the head, but directly in the crotch. 

Bob is there with a wealthy fiancée, played by Chloe Fineman from "Saturday Night Live." Marge accuses him of marrying for money, but Bob denies it, offering a proposal to the Simpsons. They can go to the police with whatever accusations they may have, or they can stay mum and enjoy the free amenities that the resort has to offer. A truce is struck. Homer adds, "But if your wife turns up dead, even once, we're calling the cops." 

The episode will be one of the first in the show's 36th gangbusters season. "The Simpsons" has now lasted six years longer than the Thirty Years Wars.