While The Simpsons gave most of its heroes a happy ending in its best Christmas-set future episode, there was a dark fate in store for one major character. The Simpsons has a thorny relationship with canon. The show has an elastic approach to the concept, with some episodes of The Simpsons mentioning the events of earlier outings while other episodes ignore character details and plots that contradict the events of new stories.
For example, The Simpsons season 34 retconned its most reliable future as the show depicted Lisa ending up happy with Nelson even though she is in a relationship with Milhouse in 6 of the show’s 10 future-set episodes. Similarly, in The Simpsons season 23, episode 9 “Holidays of Future Passed,” Bart is depicted as a washed-up deadbeat, while other versions of the character’s future are more hopeful. However, while even Bart gets a happy ending in season 23's “Holidays of Future Passed” (as does the rest of the Simpson family, since the outing was written as a potential series finale), one supporting star has a shockingly dark fate in store.
“Holidays of Future Past” Kills Off Sideshow Bob
In “Holidays of Future Passed,” the iconic villain Sideshow Bob is revealed to have died offscreen at some unspecified point. While this is brutal enough, The Simpsons Christmas special digs the knife in further by barely even addressing the death. Sideshow Bob’s death is revealed in a blink-and-you’ll-miss-out background gag where his recognizable silhouette is one of the chalk outlines on Moe’s floor. The characters don’t even comment on Sideshow Bob’s passing even though, judging by the outline, he was most likely murdered (that said, his many attempts on Bart’s life do give the Simpson clan reason to dismiss his demise).
The Simpsons Changed Sideshow Bob’s Future (Repeatedly)
While it is brutal to see that Sideshow Bob ends up dead on the floor in Moe’s bar, fans of the supporting star can rest assured that his fate is not set in stone. While The Simpsons' future problem means that the show sometimes contradicts the events of earlier episodes by depicting a new version of the same character’s future, this tendency might be enough to save Sideshow Bob’s future. After all, in one later Christmas episode, The Simpsons season 29, episode 9, “Gone Boy,” it is revealed in a flash-forward that Sideshow Bob lived into old age (although he also wasted his life pursuing vengeance against Bart).
Meanwhile, in season 31, episode 10, “Bobby It’s Cold Outside,” Sideshow Bob buries his beef and forgives Bart, moving on and finding a new purpose (and eventually even standing in for Santa Claus and inadvertently finding love). Since The Simpsons season 34 saw Maggie speak, Bart team up with Skinner, and numerous other unlikely events, it is likely that the outing will once again retcon this Sideshow Bob future with another, even less likely ending for the character. However, for now, Sideshow Bob survives one of The Simpsons futures, but he is killed off in the show’s sweetest ending.