22. Vern Schillinger, 'Oz'
Long before he terrified Peter Parker as J. Jonah Jameson or triggered PTSD flashbacks for music majors everywhere in Whiplash, J.K. Simmons was the influential HBO prison drama's equivalent of the Wicked Witch of the West. Only instead of a broomstick and an army of flying monkeys, he had penchant for rape and terrorizing the penitentiary's inmates, with an army of white-supremacist gang members to back it up. And his torment of, and payback by, his nebbishy "prag" Tobias Beecher was the show's most visceral example of Oz's villain/victim dynamic.