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“The Simpsons” is a show that’s usually a slave to its status quo. Almost nobody in the series grows older and almost nobody’s allowed to make major life changes that stick. This is part of why the special non-canon episodes, like the “Treehouse of Horror” specials or those occasional flashback/flashforward stories, are so fun; they’re introducing change into a show that so rarely offers any.

But even though life in Springfield has stayed oddly static throughout the past 38 years, major events do happen. Sometimes a character we all know and love will die, and the characters will mourn their death for many seasons afterward. “The Simpsons” doesn’t kill off quite as many established characters as some of its competitive shows like “Family Guy,” but when they do kill someone off it tends to hit a lot harder. So, here’s a list of all the significant deaths in “The Simpsons,” ranging from the deeply sad ones to the bizarre and random. 

Obligatory reminder: spoilers below!

It seems fitting that the first recurring character’s death on “The Simpsons” was a friend of Lisa, the most sensitive member of the family. In season 6’s “Round Springfield,” the charming jazz musician dies of an apparent heart attack off-screen. It’s devastating news for Lisa, especially since she was just about to share with him some good news. 

Bleeding Gums Murphy serves a similar purpose to Mr. Bergstrom from season 2′ “Lisa’s Substitute,” in that he’s a smart, trustworthy adult who sees Lisa’s value and gives her hope that things will get better. (It’s tough being the only normal person in a town full of idiots, after all.) Both characters only get to hang out with Lisa for a small window of time before the show whisks them away. It’s sad to see Bleeding Gums go, but at least his ghost returns in the clouds for one final song. 

This episode is uniquely grounded for season 6, a year of “The Simpsons” that was otherwise very hectic and over-the-top. In a season of chaos, the show slowed down to let Lisa go through all the stages of grief. It makes for one of the most underrated episodes in the classic era. The show itself may have joked in season 8 that Bleeding Gums was never popular (more on that soon), but Bleeding Gums will always hold a special place in my heart. 

27 years later, “The Simpsons” would introduce Bleeding Gums’ adult son Monk. The episode, “The Sound of Bleeding Gums,” serves as a nice final chapter to a Bleeding Gums trilogy. Sure, it raises a massive continuity issue (how did Monk grow into adulthood while Lisa stayed the same age!?) but that’s a small price to pay for some Bleeding Gums goodness.

Poor Grimey doesn’t quite deserve to be on this list, considering that he’s technically just a one-off character, but his episode was so memorable I’m including it anyway. “Homer’s Enemy” is all about exploring the absurdity of Homer Simpson’s life, and it does so through the lens of Frank Grimes, a man from the real world who’s had to struggle for everything he’s gotten. Poor Frank is driven crazy by how Homer is able to live out the American dream despite his extreme laziness and incompetence, all while Frank himself still has to live in a single room above a bowling alley and below another bowling alley. 

The unfairness of the world drives Frank insane, to the point where he electrocutes himself to death amidst a massive mental breakdown. To throw some extra salt in the wound, Homer rudely falls asleep at his funeral, much to the amusement of all the people who watched Frank die. 

“Homer’s Enemy” is often ranked among the best “Simpsons” episode of all time, although it has always seemed too mean spirited to me. Yes, Frank Grimes should’ve learned to let go of his envy, which is arguably the most self-destructive of all emotions. But still, what a sad way to go out. The bleak ending leaves a bad taste in my mouth, even if I do still think Homer’s line, “Change the channel, Marge!” is pretty funny. 

The good news is that the spirit of Ol’ Grimey would live on within his secret illegitimate son, Frank Grimes Jr., who tries to kill Homer in season 14’s “The Great Louse Detective.” Thankfully Jr. does not die like his father, though it appears that bitterness has conquered his soul as well.

The actress who voices Maude Flanders, Maggie Roswell, asked for a raise in 2000 to cover the commute costs for her to get from her home in Denver to the show’s studio in Los Angeles. The Fox executives were very stingy about the situation, so Roswell quit. For some of the characters she voiced, like Miss Hoover, Helen Lovejoy, and Luann Van Houten, the show simply de-emphasized them for a year or two. But for Roswell’s most important character, Maude, they chose a different route. In the first act of “Alone Again, Natura-Diddly,” Maude is hit with a T-shirt cannon and falls over a stadium railing to her death. 

It’s the sort of moment where you can’t tell at first if the show’s serious. After all, if Homer could fall down the Springfield Gorge and be perfectly fine at the start of the next episode, surely Maude could survive this fall? But no, Maude is indeed dead here. And in the 20+ years since, she’s only returned as a ghost or in flashback scenes. 

As dark as this all is, it did at least lead to an interesting long-term character arc for Ned Flanders, who must now make peace with this horrible tragedy and start looking for love all over again. Ned gets quite a few romance storylines throughout the rest of the series, which is something fans back in the classic era never would’ve expected from such a character. Maude’s death may be one of the most controversial writing choices of the series, but I think it opened up a lot of fun storytelling avenues for the entire Flanders family. Even Rod and Todd have a bit more depth to them these days. 

Although the Simpson family dog is still kicking 36 years after it was introduced, the Simpson family cat hasn’t been so lucky. The first Snowball, Snowball I, was run over by a car shortly before the show began, at least according to a family Christmas letter Marge wrote in the first episode. Snowball II then died in season 15’s “I, D’oh-Bot.” Once again, he was hit by a car — driven by Dr. Hibbert. Lisa copes by getting a third and fourth cat to replace him (named Snowball III and Snowball IV respectively), but the third one drowns in the fish tank and the fourth one jumps out the window and very much does not land on its feet. 

Finally Lisa finds Snowball V, a cat who looks and acts exactly like Snowball II. Lisa decides to name him Snowball II so she can pretend those previous three cat deaths never happened, and sure enough those grisly events are never mentioned again. It’s a bad episode. But hey, at least Snowball II gets to live on in the show in spirit, if not in the flesh. And at least poor, never-seen Snowball I gets to have a lasting impression on the series; the original cat’s name lives on, plus we did get to hear Lisa’s poem on the subject. 

Amber’s an odd addition to this list, because she’s not a particularly well-known character. If you’re one of those stickler “Simpsons” fans who doesn’t watch anything past the classic era, you probably didn’t even know she existed. Well, Amber showed up in season 10’s “Viva Ned Flanders.” In this episode, Homer and Ned have a wild night in Las Vegas, only to wake up and find that they both married two barmaids. The woman Homer married is Amber. 

“Viva Ned Flanders” doesn’t really resolve this storyline much; when the storyline returns in season 13’s “Brawl in the Family” Ned is no longer married, so it’s pretty much only Homer who has to seriously worry about the situation. Amber tries to wreck Homer and Marge’s marriage, but Homer tricks Amber into getting drunk and marrying Grandpa; the scheme works and Amber heads back off to Vegas. Four seasons later, a season 18 episode (“Jazzy and the Pussycats”) starts off with Amber’s funeral, revealing that she has died from an overdose at a rollercoaster theme park. 

And, well, that’s pretty much it for Amber. None of her episodes are particularly well-liked among fans and she’s rarely mentioned again on the show itself, so it’s easy for even long-time “Simpsons” fans to forget about her. It doesn’t help that this show has had a million storylines where Homer and Marge’s marriage is on the rocks, so viewers’ patience for Amber’s storyline was strained from the second she showed up. Still, rest in peace, Amber! I’m sure golden era “Simpsons” episode could’ve given you a better arc.

Of all the long-running story arcs on “The Simpsons,” is there any as cruel as the one with Mona Simpson? Voiced by Glenn Close, Mona is Homer’s long-lost mother, who keeps trying to return to Homer’s life only to be thwarted by the show’s love for its status quo. Having someone as stable and wise as Mona in the Simpson household would seriously disrupt a lot of the stories the show could tell, so “The Simpsons” ended Mona’s first few appearances by having her run away from the law again. 

In season 19’s “Mona Leaves-A,” Mona returns to try to make things up to Homer, promising to stick around for good this time. Homer originally spurns her, having gotten his hopes up with her too many times already. He then tries to apologize for his harsh words, only to find out that she’s left him yet again, this time permanently. Poor Homer! On the bright side, “Mona Leaves-A” isn’t as much of a downer as its premise implies. Its final act revolves around Homer fulfilling Mona’s plans to stop Mr. Burns from sending a missile full of nuclear waste to the Amazon Rainforest. Mona may have died, but at least her rebellious spirit has lived on. 

This is one of those weird “Simpsons” fun facts that always bewilders the fans who’ve long stopped watching. In season 22’s “Donnie Fatso,” Homer goes undercover with the mob, gaining the trust of Springfield’s main mob boss, Fat Tony. When Homer inevitably lets slip that he’s a mole for the FBI, Fat Tony is so betrayed he has a heart attack and dies. Yes, really. It’s a canon death. 

The reason some of the more casual fans may not have heard about this plot point is because of what happens next: Fat Tony’s crew is taken over by his cousin, Fit Tony, who is basically the same as the original character but in good shape. The stress of the job quickly gets to Fit Tony however; he gains weight and begins to look exactly like Fat Tony did. His nickname changes, and the character is simply referred to as Fat Tony from that point forward. So, the Fat Tony we’ve seen throughout the past 14 seasons hasn’t actually been the original Fat Tony we’ve known and love, but much like Snowball V it doesn’t seem to matter. 

Whereas Lisa’s schoolteacher Miss Hoover has never made a strong impression, fans have loved Bart’s teacher, Miss Edna Krabappel, from the moment she was introduced. She’s charmingly cranky, burnt out, and bad at holding down a man, but she does genuinely care about the kids even if they drive her crazy. And although I for one am disappointed the show backed away from her romance with Principal Skinner, it did at least lead to one of the most surprising romantic pairings on the entire series: Edna and Ned. These two should not work together, but it turns out that opposites not only attract but they make for a fun duo. 

Unfortunately, the actress for Krabappel, Marcia Wallace, passed away in October 2013. Her character has been quietly retired on the show since 2014, and since then Bart’s fourth grade class has been taught by a string of guest stars, and then eventually by Mrs. Peyton (voiced by Kerry Washington). 

The show hasn’t lingered too much on Krabappel’s death, although it’s made a point to show just how unfortunate a love life Ned Flanders has had. Not only was his first wife murdered by a t-shirt cannon, but his second chance at love died young too. At least the second time wasn’t quite as traumatic. 

Oh no, not beloved Simpsons character Rabbi Krustofsky! Voiced by Jackie Mason (and sometimes by Dan Castellaneta), Krustofsky was Krusty the Clown’s disapproving father. He’s a respected rabbi in Springfield’s Lower East Side (yes, they have one of those), and he pops by the show occasionally to add to whatever father issues Krusty is currently going through. In the season 26 premiere, “Clown in the Dumps,” Krusty goes to Krustofsky to ask for advice. Krustofsky explains how he doesn’t really find Krusty all that funny, but dies before he can fully finish his point. 

For most “Simpsons” fans, Krustofksy’s death is known for the insane marketing Fox pulled around it. This was the season 26 premiere, and in the weeks ahead Fox kept hyping up the fact that a beloved established Simpsons character would die. They released an image featuring some floating heads of the “Simpsons” characters, with the text reading, “On September 28th, one will die…” It’s a pretty funny image, given that most of the characters on it (like the immediate Simpson family, Moe, Apu) are almost certainly too important for the show to actually kill off. Of the characters shown, only Krustofsky and maybe Marge’s mother were believable targets. 

Oh no, not Larry too! Larry was a treasured character who’s been on the show since season 1. Who can forget that big scene where he silently sat a few stools down from Homer at Moe’s Tavern? Or that other iconic scene where he sat silently at a booth behind Homer, also in Moe’s Tavern? 

Alright, so Larry was never all that important to Homer or the viewers, but Homer sure was important to Larry. That’s what we found out in season 35’s “Cremains of the Day,” where Larry dies and Homer finds out that Larry considered him his best friend. The show treats us to a glimpse into poor Larry’s life, revealing a lonely man who always just wanted to be included but never was. It turns out that the only way he could get Homer’s attention was by dying, and even then it was only briefly. 

“Cremains of the Day” was one of the best-received episodes of latter-day “Simpsons,” and part of a growing trend of the show getting increasingly self-referential. The whole episode feels like a meta joke about the writers running out of new things to do, so they’ve turned to killing off a background character and pretending like they had a big backstory sketched out for him the whole time. It makes you wonder what minor background character the show’s planning to kill off next. Maybe Bart’s classmate Richard is next on the show’s death list. 

This is a weird one. Dr. Marvin Monroe is a local counselor first introduced in season 1’s “There’s No Disgrace Like Home,” in which he tries to use shock therapy to fix the Simpson family’s constant fighting. Monroe showed up a couple more times throughout the first two seasons, and then disappeared. During the show’s very meta “138th Episode Spectacular,” there’s a meta trivia question where Troy McClure says, “Which popular Simpsons characters have died in the past year? If you said Bleeding Gums Murphy and Doctor Marvin Monroe, you are wrong: they were never popular.”

It was a moment that made fans everywhere say, “Wait, Monroe died? When?” Bleeding Gums got his own special episode about his death, whereas Monroe’s death must’ve happened off-screen (the only other confirmation of Monroe’s death came via a hospital named Marvin Monroe Memorial Hospital). The most likely explanation is simply that Monroe was just one of those early-show characters that never quite stuck, like Bart’s school friends Richard and Lewis. But whereas Richard and Lewis were simply relegated to the background for the rest of the series, with Monroe the show went the extra step of establishing he’d died, and referenced his death repeatedly in subsequent seasons. 

But then in a season 15 episode, Monroe shows up again, explaining that he had merely “been very sick.” But then in season 29’s “Flanders’ Ladder,” Monroe is depicted as a ghost, and then in “Homer’s Adventures Through the Windshield Glass,” Monroe is depicted as being down in hell. I’m not sure what to make of this, frankly. I say if anyone asks about him, let’s just tell them Monroe’s dead and let that be the end of it.