In a thrilling new twist for fans of The Simpsons, Season 36 is set to bring back the ever-mischievous Sideshow Bob for an unforgettable family vacation. The anticipation is palpable as the beloved animated series gears up for another dynamic season, where the Springfield family is forced to share vacation space with their notorious nemesis.
Sideshow Bob made his debut on The Simpsons in the classic episode “The Telltale Head,” which aired on February 25, 1990. Initially just a background character on The Krusty the Clown Show, his role quickly escalated. The character, voiced by Kelsey Grammer, became a significant part of the series’ universe when he orchestrated a plot to frame Krusty for armed robbery in “Krusty Gets Busted,” just weeks after his first appearance. Bob’s grievances against Bart Simpson, who exposed his scheme, propelled him into a vendetta that has become a staple of his character’s narrative arc.
Over the years, Bob’s elaborate schemes have led him to commit increasingly outrageous acts. From his attempts to marry Bart’s aunt Selma in “Black Widower” to his infamous pursuit of Bart in “Cape Feare,” Bob has solidified his status as one of the most iconic villains in television history. Now, in a delightful parody of the hit series “The White Lotus,” Bob returns to wreak havoc on the Simpson family’s vacation.
In a preview shared by Entertainment Weekly, the episode teases a scenario that sees the Simpsons inadvertently squatting at a luxurious resort where Sideshow Bob is also staying. In a comedic twist, when Marge suggests they leave their unexpected vacation spot, Homer tells her that Bob’s past attempts on their lives haven’t quite justified their departure. Caught red-handed, Sideshow Bob confronts them, claiming to have gone straight since his villainous days. He introduces what he boasts is his new invention: a rake that doesn’t hit you in the face when stepped on—a nod to a hilarious moment from “Cape Feare.”
Joined by a wealthy fiancée, portrayed by Saturday Night Live’s Chloe Fineman, Bob tries to pitch a deal to the Simpsons: remain silent about his past misdeeds, or enjoy the resort’s amenities while they can. The tension culminates in a humorous exchange where Homer bluntly declares they will call the cops if Bob’s fiancée ends up dead.
This episode promises to be a standout in The Simpsons’ rich legacy, which has now entertained audiences for an astonishing duration, eclipsing even historical events like the Thirty Years’ War. Fans eagerly await what comedic chaos will ensue when their favorite family is forced to coexist with the very villain they’ve loathed for decades.
