The majority of naughtiness called out on this list falls into the “so bad it’s good” category; Madison Bell’s bad tendencies, however, are too unhinged to get such a pass. Played by the undeniably attractive Erika Christensen, Madison is at least nice to look at, even when her crazy ass is systematically destroying the life of her unhealthy obsession, a high school swimming star (Jesse Bradford).

Her loony courtship tactics start off agreeable enough, with a wet and wild in-pool seduction; problem is, though, dude has a girlfriend. Not that Madison gives a damn; shortly after smashing inside the chlorine tank, she befriends his girl and tells her about the soaked intercourse. That’s just the beginning of Madison’s madness, which culminates in her escaping police custody to abduct swimmer boy’s hospitalized wifey. So much for the notion that having sex with still-flowered girls turns them into the worst kind of stage-five clingers; Madison has them all beat.