Seymour Skinner (seasons 9-30)

Seymour Skinner is a major character and an antagonist from the long-running American animated sitcom The Simpsons. He is Bart Simpson's principal, and arch-nemesis. Sadly, he was flanderized.

Why He Didn't Deserve Steamed Hams
Note: This only applies to his character as depicted in Seasons 9-30 of The Simpsons, as he was flanderized.
 * 1) Unlike most other The Simpsons characters who were flanderized, Skinner's character was ruined very quickly and not only did he suffer flanderization, but he also had one of the worst character derailments in the show. Early appearances had him mainly as a reasonably competent, no-nonsense principal who was a Vietnam veteran and had an overbearing mother, but in the episode "The Principal and the Pauper", it threw all of Skinner's backstory and personality out of the window and it revealed that he was nothing more than just an imposter named "Armin Tamazarian", not only did it see that this reveal see that the show was starting experience a decline in quality, but it also single-handedly ruined Seymour Skinner's character.
 * 2) *Even though the episode has been deemed to be non-canon by the crew members, it still doesn't save the fact the change in Skinner's character caused so much outrage by fans. His imposter nickname was even referenced in the season 15 episode "I, (Annoyed Grunt)-bot" when Lisa got a new cat named Snowball V, but decided to name it Snowball II due to its resemblance to the original cat.
 * 3) After a few seasons, he became a pathological mama's boy who was still a virgin in his 40s and merely embarrassed himself whenever he tried to assert authority over Bart or any other students.
 * 4) His relationship with Bart has changed completely, which was friend-foe but he happened to be Bart causing havoc and crying like a baby.
 * 5) He has become a pathetic subject, pretending to be intimidating or abusive towards children and Willie, but is actually a cowardly crybaby when he talks or hangs out with Superintendent Chalmers and his Mother.
 * 6) He went from being a war veteran with post-traumatic stress disorder, to a subject without self-esteem and without identity.
 * 7) Due to his break-up with Edna Krabappel (who eventually died), he is unable to get a partner.
 * 8) The relationship with Mother has become sickly, where instead of looking like Agnes's son, he seems more like her husband.
 * 9) Due to his constant dependence on his mother, he is falling infamously and sickly in love with her (In fact in the episode "Days of the Future Future", it is made clear that he married his mother).
 * 10) Due to the episodes "The Principal and the Pauper" and "My Big Fat Geek Wedding", he happened to make a punching bag mainly for jokes about how his life has become pathetic and his constant depression.
 * 11) He provoked Bart into pranking more by pranking him in front of the whole school.

Redeeming Qualities

 * 1) He is a bit simpathetic because he has an overbearing mother who still treats him like a child and never seems to accept the fact he's a grown man.
 * 2) *Of course, this was also the reason why he was a ruthless principal prone to treat students poorly.
 * 3) He was a much better character in the first eight seasons and has started to slightly improve as a character since season 31, although some of his flaws still remain.
 * 4) Harry Shearer still does a good job voicing him, as always.