Played By: Jennifer Aniston
Movie: Derailed (2005)
Possibly the foulest chick on this list, Lucinda Harris runs an elaborate racket with her boyfriend Philippe and his main goon (Vincent Cassel, Xzibit) to ensnare rich, married businessmen and take them for all they've got. She pretends to be a married businesswoman herself and stages innocent meet-cutes during the morning commute, which in no time at all results in drinks and a motel room to consummate the attraction. Only, it never goes further than that because Philippe bursts in pretending to be a random mugger, knocks the hapless dude out and "rapes" her before dipping out.
The mark is then blackmailed into giving up more money, with the guilt of Lucinda's fake assault looming over them as a shameful incentive. Like we said, grimey to the highest degree.