The Simpsons is full of shockingly tragic characters, with many Springfield residents actually having incredibly bittersweet backstories. But there's one figure, usually the comic foil to Bart's pranks, that stands above the rest. Seymour Skinner might be one of the saddest characters in Springfield -- with some potential signs of cracking mentally as well.
Despite the brief revelations that Seymour Skinner was actually an imposter named Armin Tamzarian, other episodes across the series have leaned towards the idea that Skinner is the genuine son of Agnes Skinner. A domineering and cruel woman, Agnes raised her son with a certain level of contempt. Many episodes, such as Season 21's "Boy Meets Curl," suggest this may have to do something with Seymour's father leaving the pregnant Agnes behind as he moved on in life, and being pregnant with Seymour directly led to her failure to win in the Olympics.
Season 29's "Grampy Can Ya Hear Me" also revealed that despite her outright dislike for her son, Agnes still couldn't stand the thought of him leaving her, which prompted her to hide that he'd been accepted to Ohio State University as a teenager with a full scholarship. Instead, Skinner ended up joining the Army and serving during the Vietnam War. Flashbacks throughout the series paint a horrifying experience for Skinner that shows him witnessing the sudden and brutal deaths of many of his friends. He was even taken captive for a period and tortured by the Viet Cong. Episodes like Season 7's "Team Homer" suggested he spent years in these horrendous conditions before finally returning to the United States
After taking a job with Springfield Elementary, Skinner embraced a boring and stern demeanor with any flashes of personality being beaten down by his mother and his newfound employer, Superintendent Chalmers. Skinner's life is positively tragic, and he struggles to connect with others. His frequent attempts to impress Chalmers could be seen as Skinner trying to connect with a male father figure and failing as Chalmers is often exhausted by Skinner's antics.
Agnes has only grown more bitter in her old age, insulting her son frequently, and, in one instance (admittedly during a non-canon entry in Season 25's "Treehouse of Horror XXIV"), Agnes caused Skinner to have a panic attack due to her insults -- only to make it worse by beating him with a purse. Skinner's shown to have no real friends and Groundskeeper Willie is often forced to hang out with him. His only significant romance was with Edna Krabappel, but his personal hang-ups and doubts led him to ruin the romance just as they approached marriage.
All of this trauma has also given Skinner a particular edge that contrasts with his usual pushover personality. Reflecting on his time in Vietnam often leaves Skinner in a mentally dark place, with his tone and body language becoming more rigid and harsh. It's also been implied that aspects of Skinner's life loosely mirrors Norman Bates from Psycho. The Simpsons repeatedly compares him to the murderous man primarily because of their terrible relationships with their mothers. Seeking a psychiatrist in Season 6's "Fear of Flying," it's implied that Skinner subconsciously considers smothering his mother and Season 25's "Yellow Subterfuge" revealed that he believed life would improve without his mother after faking her death for a prank.
Skinner is a particularly tragic figure in Springfield, an unimpressive and oft-forgotten man whose mother kept him from ever achieving the kind of life he wanted. He's one of the more traumatized characters in the series, and if there was anyone who could have the potential to actually snap, it would be him.
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