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Lindsay Lohan starred in 'Disney's The Parent Trap' in 1998 when she was 13. She later starred in the 2004 movie 'Mean Girls'. She also guest-starred on the ABC show 'Ugly Betty' in 2008. However, in recent years, she has faced a slew of personal troubles and has been sent to jail a handful of times for violating her probation in a 2007 drunken driving an cocaine possession case. As of December 2011, she is free and trying to resurrect her acting career. That month, she posed nude for Playboy magazine, channeling Hollywood icon Marilyn Monroe.
(Playboy / Walt Disney Pictures)