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 has been infamously in love with her.
 * 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.