The Simpsons is known for creating some of the most iconic characters in animation history, yet some of them have changed immensely over the course of the show’s run. The titular family and the citizens of Springfield have prevailed for decades that the series has been on the air, and while The Simpsons is an episodic sitcom, some stories have made some pretty drastic alterations to a handful of characters’ arcs, backgrounds, personalities, and more.
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Since its premiere in December 1989, The Simpsons has run for 37 seasons, with 799 episodes having been released as of the writing of this article. The Simpsons will release its 800th episode on February 17, 2025, and with a second movie and more seasons on the way, the show is far from over. With hundreds of original characters appearing throughout the decades, some are bound to have changed. However, these seven major characters have seen the most drastic alterations since their first appearances.
7) Waylon Smithers

Mr. Smithers is the assistant of Mr. Burns, with him being known for his loyalty and attraction to his boss. Although Smithers’ voice was heard in the show’s premiere, Smithers first appeared in The Simpsons season 1, episode 3, “Homer’s Odyssey.” Here, Smithers sported a completely different look than every appearance since, with him having a much darker skin tone and blue hair.
However, Smithers’ appearance is far from the only way that he has changed. Smithers’ role in The Simpsons has also shifted massively. For the first few decades of Smithers’ existence, he played the stereotype of a closeted gay man. Most of the jokes surrounding the character had to do with his sexuality, although he was never confirmed to be gay for the longest time. Smithers finally came out in season 27, episode 17, “The Burns Cage,” fundamentally changing the mystery that surrounded his character from the very beginning.
6) Chief Wiggum

Springfield Chief of Police Clancy Wiggum is a stereotypical bumbling cop, and another The Simpsons character who has changed significantly. His appearance has altered since his debut in “Homer’s Odyssey,” with his hair starting blue, turning black in later episodes, and then turning blue again. Chief Wiggum also started as a corrupt police officer, although later appearances focused on his laziness more than his criminality.
5) Ned Flanders

Ned Flanders has been Homer Simpson’s neighbor since the show’s premiere, and since his debut, he has changed a lot. Flanders was initially representative of the ideal family man, with his happy home life being juxtaposed with that of the titular family. As time has gone on, however, Flanders’ characterization has mostly shifted to focus on his religiosity, while episodes like “Huricane Neddy” have shown that Ned has more layers than he initially let on.
Flanders’ change in characterization is probably the most well-known example from The Simpsons, as the term “Flanderization” is the namesake of the character. Flanderization refers to the media trend of characters being dumbed down to their most recognizable traits, with the pivot to Flanders’ overexaggerated religiosity being the prime example of this.
4) Nelson Muntz

Nelson Muntz is a typical school bully, with him terrorizing Bart and Lisa at Springfield Elementary School. Nelson first appeared in season 1, episode 5, “Bart the General,” where Bart gets the help of his grandpa in order to fight back against the bully.
Although Nelson started out as a one-dimensional jerk, he has surprisingly become one of the most sympathetic and tragic characters in The Simpsons. The Muntz’s financial insecurity and Nelson’s rough home life have become a major focus of many of his stories, with the show using this to explain why Nelson is the way he is. Nelson even dated Lisa in season 8, showing that he can fill the slot of a love interest rather than a bully.
3) Principal Skinner

Skinner is the principal of Springfield Elementary School, and while his personality and appearance have remained consistent throughout The Simpsons, he has had the biggest story change of any character by far. Although he first appeared in the series premiere, season 7, episode 9, “The Principal and the Pauper” was not who he said he was, making it one of the most controversial episodes of the show.
As it turns out, Skinner’s real name is Armin Tamzarian. While in the army, Armin met the real Seymour Skinner, who went missing after the war. When Armin got home, he took over Skinner’s life, taking his name and becoming a school principal. Although this story has never been retconned out of existence, The Simpsons mostly ignores the reveal now, outside of a few throwaway jokes at the episode’s expense.
2) Ralph Wiggum

Although Chief Wiggum has changed since his first appearance, his son Ralph has changed even more significantly. Ralph first appeared in The Simpsons‘ premiere as part of of the Santas around the world performance, and is basically just completely normal. Compare that to basically any other school performance he later puts on, and it’s like a totally different character took over.
Throughout the first few seasons, he was portrayed as a little dim, but as time has gone on, however, Ralph has been Flanderized. His initial denseness has been overexaggerated so much that Ralph is basically just there to spout non-sequiturs, with him being so weird that he barely acts like a human.
1) Lisa Simpson

Although she is now known for being a goody-two-shoes, this wasn’t always the case for Lisa Simpson. In early seasons, Lisa was a lot like her brother Bart, with the duo getting into trouble pretty frequently. However, Lisa is now defined by her political activism, with her barely acting like a kid at all. Lisa’s well-known conversion to veganism and Buddhism are major landmarks in her development, but now that she has been at the center of so many unpopular modern The Simpsons episodes, she is basically unrecognizable from her first appearance.
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