7. Lindsay Lohan
Lindsay Lohan started out as that cute kid who did a charming turn in the remake of The Parent Trap, then turned into a capable actress that had a string of hits that included Freaky Friday and Mean Girls. But somewhere along the way, the talented redhead just completely imploded, and her hard partying ways started to overshadow her up and coming career. Like her former buddy Paris Hilton, Lohan had a few run-ins with the law before being sent to jail for violating her probation.
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Also like Hilton, Lohan served a reduced sentence, although hers was at home due to overcrowding. She was sent to jail again for violating her community service agreement, and spent a total of five hours in the slammer due to (you guessed it) overcrowding. Lohan tried making several comebacks, and while they weren’t super successful, they did show that she was able to laugh at herself along with everyone else.
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