Crime: DUI and drug possession Served: Too many to count. The longest stint was 14 days. Given how much her extra-curricular activities dominate her reputation its easy to forget that Lindsay Lohan was once an actress who could stand on her talents; now any role she has is in direct reference to her troubles. A child star (that old chestnut), Lohan looked set to remain in the limelight on the back of great turns in the likes of Mean Girls and a strong public image; she fronted multiple fashion brands and presented herself as incredibly politically minded. And while she did remain in the publics eye, it wasnt in the way we all expected. Meticulously documented by online gossip sites, Lohans repeated arrests for drink driving and possession of cocaine led to a complete nose-dive of her reputation. For years alternating between rehab and being on the brink of returning, she spent time in jail multiple times, never for that long, but substantial enough to make the list.
