Over its 33 seasons, The Simpsons has featured some truly impressive guest stars, only a select few celebrities have actually been killed off. Despite its elastic continuity, The Simpsons is not overly fond of permanently retiring characters. The number of characters that The Simpsons has killed off in canon is shockingly low, given the show’s zany tone and its massive number of episodes, meaning it is even rarer for the show to kill a celebrity guest star.
However, in its early years, The Simpsons was famous for taking swipes at anyone and everyone, and no celebrity was too famous to escape the show's acerbic wit. At the height of the show’s acclaim, The Simpsons even leveled a gag at the then-sitting US president George H Bush after he claimed American families should be “more like the Waltons and less like The Simpsons.” In a cold open, Bart famously responded that, just like the Waltons, the Simpsons family were praying for an end to the depression, too.
However, despite this once-strong satirical verve, in recent seasons The Simpsons has earned criticism for the show having a fawning attitude toward celebrity guest stars. Lady Gaga and Elon Musk’s much-hated Simpsons cameos, in particular, irked fans who felt the Simpsons and the rest of the show's characters were too in awe of the week’s guest stars to criticize or poke fun at the famous faces. This was not always the case as, throughout its 33 seasons, The Simpsons has occasionally been willing to harm, mock, and even kill off celebrities for the sake of a gag. While the show may not be South Park, The Simpsons can on occasion skewer celebrities to death as proven by these examples.
Ernest Borgnine
Famous for everything from the ‘50s classics From Here To Eternity and Bad Day at Black Rock to the ‘90s classics Small Soldiers and BASEketball, Ernest Borgnine was an impressively game screen veteran who guest starred as himself in “Boy-Scoutz ’n’ The Hood” (season 5, episode 8). Unfortunately for Borgnine, he suffers one of The Simpsons’ darkest non-Treehouse of Horror fates. Introduced as a “celebrity dad” who is attending Bart’s boy scout camping trip, Borgnine is last seen onscreen telling a scary campfire story to a group of boy scouts. Since his cameo then ends with some unseen monster emerging from the woods to attack Borgnine and him screaming in terror, things don’t look good for the actor’s survival.
James Caan
James Caan played himself in season 16’s “All’s Fair In Oven War,” appearing briefly as an attendee of Bart’s swanky treehouse lounge. Unfortunately for the short-lived actor, his cameo ends when the minor Simpsons character Cletus shoots him for attempting to woo Cletus’ long-time love interest, Brandine. Caan is gunned down by Cletus in a recreation of his character in The Godfather’s unforgettable demise, making him the second celebrity playing himself on The Simpsons who ended being brutally killed off in exchange for their good-humored efforts.
Green Day
The pop-punk group Green Day played Lake Springfield in the opening scenes of The Simpsons Movie, where they provide a rock-inflected cover of the show’s usual theme music. However, the barge that the band is performing on begins to dissolve thanks to the lake’s lethal pollution levels. Ironically, the stage starts melting as the band attempt to talk about the lake’s level of pollution, and the townspeople choose to boo the group instead of helping out. In a surprisingly dark gag, the members of Green Day are confirmed to die as a result of this when a memorial service later takes place for them in Springfield’s church. It is hard to deny that Springfield’s citizens were the villains in this instance, although the band isn't mentioned for the remainder of The Simpsons Movie after their unfortunate passing.
Courtney Love, Spike Lee, Tom Arnold, Tonya Harding, Rosie O’Donnell, Pauly Shore
This veritable who’s who of minor (and, according to The Simpsons at least, annoying) early ‘00s celebrities die alongside Bart and Homer in "Treehouse of Horror X," (season 11, episode 4) aboard a rocket ship headed straight to the sun. Although the Treehouse of Horror segments are not typically viewed as canon, the annual Halloween specials have allowed the series to kill off both Springfield locals and scores of famous stars at the same time. The Simpsons’ playful approach to continuity means that these deaths may or may not be part of the show’s continuity, but either way, this highly-ranked Treehouse of Horror outing represents one of The Simpsons’ biggest celebrity killing sprees so far.
Los Lobos
Although they are never actually seen onscreen, the rock band Los Lobos reportedly dies in a blimp crash in “Thank God It’s Doomsday” (season 16, episode 19). The incident occurs offscreen during “Krusty’s Celebrity Salute to Specials,” and it is one of many moments that Homer reads as a sign of the end times since “the stars are falling to earth," as he punningly points out. Unfortunately for the rest of the cast, this is seen as pretty convincing evidence by much of Springfield, and Homer is soon seen as some sort of messiah. Luckily, the citizens of Springfield soon see sense, and Los Lobos even get to cover the iconic The Simpsons theme song during the episode’s end credits (even if they presumably remain dead according to the show’s canon).
Prince, Neil Armstrong, George Clooney
Legendary musician Prince, astronaut Neil Armstrong, and blockbuster star George Clooney do not, at first glance, appear to have much in common. However, the trio is three of the celebrities who Homer is hired to assassinate in the Treehouse of Horror segment “How To Get Ahead In Dead-vertising,” to allow companies to use their likenesses without having to pay pesky royalties. The segment soon trails off in another direction, but not before these three celebrities bite the bullet thanks to Homer’s surprising competence as a hitman. This Treehouse of Horror Halloween special may not see The Simpsons kill off as many celebrities as the earlier "Treehouse of Horror X," but Prince, Armstrong, and Clooney do boast the achievement of being the only celebrities who were killed by a member of The Simpsons family specifically.