The story that so clearly upsets Willie so much in Lit class and causes him to drop out is Edgar Allan Poe's "Willliam Wilson," about a young man and his doppelganger, whom he eventually murders. There are parallels between Willie's self-image regarding his betrayal of his friend/roommate, not to mention his own name, that clearly distresses him.
Ron Livingston and Stephen Root appeared together in Office Space (1999).