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At age 11, Lohan made her motion picture debut in Disney's remake of The Parent Trap , a critical and commercial success. Her next major motion picture, Disney's remake of Freaky Friday , was also a critical and commercial success. In , two driving under the influence incidents led to Lohan being put on probation, and together with three visits to rehabilitation facilities caused the loss of several movie deals. Though the album received mostly lukewarm reviews, it was certified platinum. Between and , Lohan went into rehabilitation three times, and spent much of her time entangled in legal problems stemming from misdemeanors and probation violations. Lohan's second album, titled A Little More Personal Raw , was released in December and featured darker material than her debut had. In , she starred in Paul Schrader's independent film The Canyons.

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Kennedy. Age: 30.
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At age 11, Lohan made her motion picture debut in Disney's remake of The Parent Trap , a critical and commercial success.

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Brooklynn. Age: 27.
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With the release of Mean Girls , another critical and commercial success, and Disney's Herbie: Fully Loaded , another commercial success, Lohan became a teen idol sensation, a household name and a frequent focus of paparazzi and tabloids. Lohan's second album, titled A Little More Personal Raw , was released in December and featured darker material than her debut had. She appeared in Robert Rodriguez's feature film Machete Following Just My Luck, Lohan focused on smaller, more mature roles in independent movies, receiving positive comments on her work, including A Prairie Home Companion , Bobby and Chapter 27 Though the album received mostly lukewarm reviews, it was certified platinum. Lohan's debut studio album, titled Speak, was released in December and became the first high-seller from Casablanca in several years, selling 1 million copies in the United States alone and peaking at number four on the Billboard After recording several songs for her movie soundtracks, Lohan signed with Casablanca Records.

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