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 Sucks Now

 * 1) Unlike most other The Simpsons characters who were flanderized, Skinner was flanderized very quickly. Early appearances had him mainly as a reasonably competent, no-nonsense principal who was a Vietnam veteran and had an overbearing mother.
 * 2) He even managed to be pretty badass in a few episodes ("The Boy Who Knew Too Much").
 * 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 even became an unfunny jerk within the process.
 * 6) 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.
 * 7) He went from being a war veteran with post-traumatic stress disorder, to a subject without self-esteem and without identity.
 * 8) Due to his break-up with Edna Krabappel, he is unable to get a partner.
 * 9) The relationship with Mother has become sickly, where instead of looking like Agnes's son, he seems more like her husband.
 * 10) 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).
 * 11) 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.
 * 12) He provoked Bart into pranking more by pranking him in front of the whole school.