| Seymour Skinner (aka "Spanky") is the principal of Springfield Elementary School in The Simpsons universe. Eternally clad in his powder-blue suit and store-bought haircut (not a toupee1, however) he rules the school with an iron fist (if only in his mind, at least). His chief nemesis is one Bart Simpson, a fourth grader who has brought Skinner more pain and misery than any principal is entitled to. Skinner still lives with his mother, Agnes, because (as he claims) she is dependant on him, but to see them together it's obvious who controls their relationship. Seymour was also a member of the famous Be Sharps barbershop quartet in the 1980s and was presumed murdered by Fat Tony, the local mobster, in 1991. In reality he had been trapped under a stack of newspapers from which he eventually freed himself.
After serving a hitch in Vietnam with the army2 (he spent part of his tour of duty as a prisoner of war) Seymour returned to Springfield and began teaching fourth grade science. Eventually he rose through the ranks of the school to become principal. He's been fired from this job on several occassions, but he always returns to his former post in the end. His early confrontational relationship with teacher Edna Krabapple eventually blossomed into romance and the two were to be married until she broke off the engagement in 2004. This was Seymour's first romantic relationship since his marriage proposal was turned down by Patty Bouvier in 1991.
Superintendent Chalmers often drops in at the school for surprise inspections, and his presence is a constant source of worry for Skinner. Once Skinner became so flustered at Chalmers's surprise appearance that he asked him "How are you going?". Another time, in a plan to pass off Krusty Burgers as his own cooking, Skinner referred to the burgers as "steamed hams" despite the fact that they were obviously not ham nor were they steamed. Chalmers tends to be as gullible as he is gruff, so Skinner often gets away with his far-out excuses and explanations.
As mentioned earlier Skinner's mother Agnes controls most of his life. She has many harsh rules that Seymour must follow, such as no talking to salespeople, no dating (a rule that he has broken), and other such policies that are typically forced upon children. Every Friday night is Silhouette Night in the Skinner house, meaning that Seymour sits by a light so as to cast a shadow of his profile on the wall for his mother to trace.
No matter how much he's beaten down, Seymour Skinner will always bounce back. For as he says, "Tomorrow is another school day!"
1 The creators had originally planned for Skinner to wear a toupee, but nobody on staff wanted to write the cheap joke of his hairpiece being torn off. The joke had been written into scripts several times over the years but was always cut from the final version. In fact, the episode "Skinner's Sense of Snow", in which Seymour and the children are trapped in the school due to snow, actually had a scene animated where Bart yanked his toupee off. It was cut for broadcast, however, because nobody was a fan of the gag.
2 The episode "The Principal and the Pauper" established that the man we knew as Seymour Skinner is actually a nogoodnik named Armin Tanzarian. However at the end of the episode this information was cancelled out by Judge Snyder and everything was restored to the status quo with the matter never to be spoken of again. As such, an "official" bio of Skinner excludes this information. | 
