They portrayed murderers, rapists, prostitutes, and victims. It sheds that “good kid” image, lemme tell ya. *Episode spoilers ahead*
Hilary Duff, Lizzie McGuire
Lizzie McGuire guest starred on an episode of Law and Order: SVU as a mother who supposedly killed her infant. This episode obviously stood in for the Casey Anthony case. Turns out her kid had measles, but she was still a crappy mother.
Jake Thomas, Lizzie McGuire
Lizzie's younger brother Matt switched from harmless pranks to rape. He guest starred on an episode of Criminal Minds as a member of a trio who kidnap, chase, rape, and murder women. To be fair, he didn't know one of his accomplices went rogue and killed them, but still. He ends up beaten to death with a baseball bat because karma's a bitch.
Raviv (Ricky) Ullman, Phil of the Future
Yep, the lovable boy from the 22nd century guest starred on an episode of Law and Order: SVU. His character raped an unconscious girl to impress a radio shock-jock.
Kay Panabaker, Phil of the Future
Debbie went from being annoying as hell to a rape victim on an episode of Law and Order: SVU. Her character goes to New York and shacks up with this homeboy. Soon after, he pimps her out to all these rich, skeevy dudes. Charming, right?