Remember the cute freckle-faced girl in Parent Trap? Lindsay Lohan was a child model for years before she landed the lead role in the 1998 Disney remake - the film that launched her movie career. She then went on to score critically-acclaimed lead roles in Freaky Friday and Mean Girls. In 2004, she recorded her first pop album Speak and released a second in 2005. However, the starlet's career has been far from a smooth ride, interrupted by spells in rehab, two counts for DUI, and a string of troubled relationships. Lindsay was sentenced to 90 days in jail in July 2010 for breaching her probation order. The American actress famously had a relationship with Samantha Ronson (DJ Mark Ronson's sister) and has been romantically linked to Calum Best, Harry Judd and The Wanted's Max George. In 2011, she posed for Playboy magazine and reportedly received a cool $1million for the spread. In the Summer of 2013, Lindsay spent 90 days in rehab and was ordered to remain in therapy until Novemver 2013, when her next court date is scheduled.