Year: 2007
Drug caught with: Allegedly heroin
Consequence: We all learned the hard way that if you're going to do something bad, don't document it through pictures and post it online. Apparently LiLo didn't get the message, as pictures of the Mean Girls actress were released depicting her with what appears to be a tourniquet and a syringe, which we can only assume had some sort of controlled substance in it.

The photos were posted just a few hours after Lohan was released from a 14-hour jail stint. Lindsay was booked into Lynwood jail after failing two drug tests while on probation. Unfortunately for Lohan, this story never seems to end.