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Paparazzi began following her and her love life and partying became frequent targets of gossip sites and the tabloid media.

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At Lohan's initiative, her character was rewritten and changed from a Goth style to be more mainstream. The first film, Disney's teen comedy Confessions of a Teenage Drama Queen, earned a domestic box office total of million, with Brandon Gray of Box Office Mojo commenting that it was "well above expectations as it was strictly for young girls." Her second lead role that year, in the teen comedy Mean Girls, marked Lohan's first movie independent of Disney.

Based in part on the non-fiction book Queen Bees and Wannabes, the film stars Lohan as a previously homeschooled 16-year-old learning to navigate the social cliques of a public high school.

At age 11, Lohan made her motion picture debut in Disney's commercially and critically successful 1998 remake of The Parent Trap.

Her next major motion picture, Disney's 2003 remake of Freaky Friday, was also a critical and commercial success.

In 2013, she starred in Paul Schrader's independent film The Canyons.

In 2014, the docu-series Lindsay aired on the Oprah Winfrey Network, and Lohan made her stage debut in the London West End production of Speed-the-Plow.In 2005, Lohan became the first person to have a My Scene celebrity doll released by Mattel.She also voiced herself in the animated direct-to-DVD film My Scene Goes Hollywood, based on the series of dolls.Lohan remained in the role for a year, before leaving to star in Disney's 1998 family comedy The Parent Trap, a remake of the 1961 movie.She played dual roles of twins, separated in infancy, who try to reunite their long-divorced parents, played by Dennis Quaid and Natasha Richardson.Between 20, Lohan went into rehabilitation three times, and spent much of her time entangled in legal problems stemming from misdemeanors and probation violations.