There are few shows that have made as big of a mark on pop culture as The Simpsons. For over more than three decades, The Simpsons has functioned as an essential piece of comedy on television and a touchstone for other adult animated programs. The Simpsons has over 700 episodes under its belt and it should come as no surprise that its earliest seasons are the most groundbreaking, but it’s fascinating to watch how The Simpsons has evolved over the years.

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The show has gradually established hundreds of characters that fill Springfield, but there are some select individuals who audiences won’t be seeing back on the series any time soon, if at all.

10 Hartman’s murder led to Troy McClure & Lionel Hutz being peacefully retired

Animation The Simpsons Lionel Hutz Empty Pizza

There are a number of reasons to retire a character and have a resident of Springfield permanently exit. However, it always stings a little more when these decisions are the result of real-life tragedies. The irreplaceable Phil Hartman voiced Springfield’s most beloved washed up actor, Troy McClure, as well as the perpetually incompetent lawyer, Lionel Hutz.

Hartman’s murder led to these iconic characters being peacefully retired. They’re not dead, but no one else will voice them to take over the roles out of respect for Hartman’s work on the series.

9 Maude Flanders' death was initially prompted by Maggie Roswell’s departure from the series

Animation The Simpsons Maude Flanders Ghost With Bart Milhouse

Ned Flanders has an optimistic disposition that sometimes turns him into an unfortunate punching bag to other citizens and even the universe. A major loss that Ned experiences is the death of his wife, Maude, which becomes a significant story arc and his family.

Maude’s death was initially prompted by Maggie Roswell’s departure from the series, but she’s since returned and continues to voice Helen Lovejoy, Luann Van Houten, and Miss Hoover. Maude has returned on the rare occasion as a ghost in a “Treehouse of Horror” special, but fans are unlikely to see her again in a noteworthy fashion.

8 Frank Grimes Turns Into A Cautionary Tale Over The Indomitable Spirit Of Homer Simpson

Animation The Simpsons Frank Grimes Leers At Homer

“Homer’s Enemy” is a cherished classic Simpsons episode that poignantly examines Homer’s ability to fail upwards from a frustrated outsider who can never catch a break. Frank Grimes’ sobering look at Homer makes for an entertaining episode with a dark underbelly to it.

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Grimes’ inability to understand the world’s love over Homer leads to the character’s own death, which continues to be undercut by Homer. Grimes has actually made a brief return appearance as a ghost, but he’s not an enemy that Homer has to continue to worry about.

7 Homer’s mother, Mona Simpson, passes away, which both Homer & Abe process in their own ways

Animation The Simpsons Mona Simpson Dies Homer Worried

The Simpsons typically goes for big laughs, but there are occasional episodes that tug at the heartstrings and explore some genuinely emotional territory. “Mother Simpson” is an early episode that looks at Homer’s complicated relationship with his estranged mother that ends in her once again leaving him.

Much later, Homer’s mother passes away, which both he and Abe process in their own ways. Mona’s voice actress, Glenn Close, is still alive and well and this casualty is instead for the dramatic weight it has on Homer.

6 Alice Glick Is A Belligerent Neighbor That Never Received Love Until It Was Too Late

Animation The Simpsons Alice Glick Death News Report

Alice Glick isn’t the most well-known Simpsons character, but she still adds some important flavor to Springfield and gives Bart plenty of frustration. Bart and Milhouse’s robot seal experiment goes wrong and apparently results in Alice Glick’s death, which Kent Brockman reports on television.

Despite Alice Glick’s reported death, the character has still appeared on random occasions throughout Springfield, although this is more a continuity error than proof that Glick faked her passing or is somehow immortal. Either way, it’s unlikely that Glick will play a significant role again and be elevated beyond a background player.

5 Sadly, Marcia Wallace passed away & so Edna’s character was retired out of respect

Animation The Simpsons Edna Krabappel Sad With Bart

Every facet of Springfield connects and there’s such a life to all of the characters that are typically reserved to Springfield Elementary. Edna Krabappel is an important part of Bart’s life as his fourth-grade teacher, but she later becomes Ned’s new wife after the passing of Maude.

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Sadly, Marcia Wallace passed away and so Edna’s character was retired out of respect. It’s not turned into a major event in the series, but there’s a somber memorial for the character through one of Bart’s opening chalkboard scrawls.

4 Dr. Marvin Monroe’s Passing Is Reserved As A Background Detail

Animation The Simpsons Dr Marvin Monroe Angry Ghost

The first season of The Simpsons really leans into the dysfunctional family aspect and the Simpsons even enter family therapy with hopes that they can “fix” themselves. This operation is run by Dr. Marvin Monroe, a brash character that doesn’t make much of an impression.

The news of Monroe’s passing is actually quite sly and revealed through the dedication of the Marvin Monroe Memorial Hospital. Monroe’s passing and the unpopular nature of his character are even joked about in “The Simpsons’ 138th Episode Spectacular” clip show. Monroe has made a ghostly cameo decades later, but it’s not a regular occurrence.

3 Krusty Comes To Terms With His Father Once Rabbi Hyman Krustofsky Passes

Animation The Simpsons Rabbi Krustofsky Lectures Krusty

Krusty the clown is typically used as a punchline or a critique on show business in The Simpsons, but he’s allowed some depth and stronger character moments whenever his father, Rabbi Hyman Krustofsky, is present. Krusty grapples with his father’s disapproval over his career path in life, which hasn’t embraced religion.

Their relationship ends on a stark note when Krusty’s father expresses his disinterest in his son’s work, only to then pass away. This forces Krusty to earnestly explore himself and his work. It’s a surprisingly powerful storyline for Krusty.

2 Lunchlady Doris Gracefully Retires To Greener Pastures after the passing of her voice actress, Doris Grau

Animation The Simpsons Lunchlady Doris Ghosts

The utility of a supporting character sometimes can’t be appreciated until they’re gone. This is largely the case for Lunchlady Doris, who was consistently entertaining and almost operated with an absurdist basis whenever her time in Springfield Elementary’s cafeteria was detailed.

Doris never got a chance to be in the spotlight like many other supporting characters on The Simpsons and the passing of her voice actress, Doris Grau, who was also the character’s namesake, ultimately prevented this from ever happening. This doesn’t change the impact that the character makes on The Simpsons’ earlier seasons.

1 Bleeding Gums Murphy’s Death Is A Catalyst For Lisa’s Development Process

The Simpsons has featured hundreds upon hundreds of celebrity voice appearances and it’s practically become a rite of passing for much of Hollywood. An early and memorable guest role is James Earl Jones as saxophone savant, Bleeding Gums Murphy.

Jones is an instance of a guest actor who returns, but the reunion between Lisa and Bleeding Gums Murphy is bittersweet. Murphy’s passing teaches Lisa an important lesson that inspires her as she becomes more worldly and mature. Murphy might have worked in a recurring role to mentor Lisa, but the surprise of his loss remains a top Simpsons moment.

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