Lindsay Lohan

Lindsay Lohan was once the freckle-faced redhead who everyone loved in family friendly comedies such as Mean Girls and The Parent Trap. Now, the starlet is more famous for her multiple trips to rehab and jail than her once-promising career. LiLo's hard-partying ways began in 2004, as did speculation that the actress suffered from an eating disorder. In 2007, the now-blonde actress did double duty, with two trips to rehab and two DUIs in that year alone. In spring of the following year, Lindsay began a volatile romance with DJ Samantha Ronson which ended in 2009. Over the next few years, LiLo went in and out of jail for reasons ranging from failing a drug test to a felony grand theft charge for reportedly stealing a $2,500 necklace.