23. Donnie Barksdale, The Gift (2000)
Played By: Keanu Reeves
Things were working out pretty well for Donnie Barksdale until the town psychic got involved. Technically, things started going bad for him when his mistress got killed, but then got really bad when the psychic found about it.
It's shocking that a film that allowed Keanu to play an abusive drunk opposite Cate Blanchett's town psychic didn't strike box office gold. The character deserves at least some props for saying, "She said I was the only man in town who knew how to fuck," on the witness stand.