4 Most Tragic Characters on The Simpsons

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Meanwhile, certain members of the Simpsons family endure all kinds of pain in their lives as part of sincere stabs at poignancy. These may look like silly cartoon characters, but they do go through real turmoil that viewers can relate to. Ahead, let’s look at the four most tragic Simpsons characters, who epitomize what a tonally complicated production this hilarious sitcom really is.

Seymour Skinner

The beleaguered Springfield Elementary School principal, Seymour Skinner, is often around just to provide a stick-in-the-mud foil for impish Bart Simpson. However, he’s also a tragic guy on many levels, including his psychological torment over his experiences as a soldier in Vietnam. In the audio commentaries for episodes like “I Love Lisa,” various Simpsons writers recall how this personality trait wasn’t necessarily meant to instill depth into Skinner. They just thought it was amusing that a cartoon character fought in Vietnam.

Whatever the intent, this quality solidified that Skinner is a haunted soul, which just makes his present, uber-lame circumstances extra tragic. Skinner is a pushover, still living with his mother (Agnes Skinner), and little definable personality beyond the studious intricacies of his job. Seymour Skinner is a bundle of PTSD and tediousness, a lethal combo making him one of Springfield’s most cursed residents.

Hans Moleman

There’s no other supporting Simpsons character who’s been through more endless comedic misery than Hans Moleman. This man isn’t just plagued by tragedy; his existence is solely defined by it. Throughout the course of the show, Moleman’s been set on fire, attacked by flocks of angry birds, hit in the groin with a football, and even taken to the electric chair in a local jail despite not getting his last meal (naturally, Homer gobbled it up). This shriveled-up fellow has no other purpose than to suffer for the amusement of Simpsons viewers. His anguish has certainly been a plus for Simpsons fans, since the trials and tribulations of Hans Moleman have inspired some of the program’s greatest gags.

Ned Flanders

True, Ned Flanders is the goody-goody Christian neighbor that’s often a thorn in Homer’s side. But he’s also a guy who’s experienced endless chaos in his personal life. That includes losing two different wives, Maude Flanders and Edna Krabappel, over his 35+ years of Simpsons exploits. The season eight installment “Hurricane Neddy” also revealed that a destructive side of this man’s personality is always lying in wait to cause mayhem. And let’s not forget all the turmoil Homer has caused Flanders. Just the amount of personal items this oaf has confiscated over the years is enough to render Ned Flanders a tragic character. Adding in so many deceased lovers and all of his other struggles makes it a miracle that Ned always wakes up with a perky smile.

Lisa Simpson

Lisa Simpson’s anguish isn’t as visually noticeable as the pain heaped on Hans Moleman. Instead, her tragic qualities are quietly reinforced over countless Simpsons episodes. She’s smart beyond her years and has so much empathy for the larger world. That makes her an outlier in the self-conceited realm of Springfield as well as her own household, where impulsive mayhem is king. Lisa is an outsider, always struggling to connect with other people her age or even the people supposedly closest to her. Cursed to be a pariah, Lisa Simpson constantly experiences crushing disappointment in her life as so many dreams and escape routes from Springfield crumble into dust.

Lisa Simpson is an audience surrogate for any viewers who ever felt at odds with the worlds they were born to. The tragedy of not fitting into society’s narrow perceptions of “normalcy” plagues the incredibly wise and thoughtful Lisa Simpson. Yet, even in the face of such a tragic existence, she never stops being herself and refuses to conform. That’s a comforting and inspiring quality ingrained into Lisa Simpson, arguably the most tragic denizen in the world of The Simpsons.

The first 35 seasons of The Simpsons are streaming on Disney+.