Lindsay Lohan Through the Years

The Parent Trap

As a child actress, Lindsay Lohan had her breakout role in Disney's 1998 remake of The Parent Trap, tackling two roles opposite Dennis Quaid and Natasha Richardson. In his positive review of the family-friendly comedy, Roger Ebert wrote that Lohan had "the same kind of sunny charm Hayley Mills projected, and a sense of mischief that makes us halfway believe in the twins' scheme."

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Life-Size

Lohan co-starred with Tyra Banks in the 2000 TV movie Life-Size, in which Banks played a Barbie-esque doll come to life.

Lindsay, Circa 2001

The fresh-faced young star (seen here in a red-carpet appearance) was poised to become a household name with 2004's Mean Girls, which would catapult her to mega-stardom followed by a jaw-dropping downward spiral with stints in jail and rehab.

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Get a Clue

Lohan further established her image as a squeaky-clean-yet-plucky tween idol in 2002's Get a Clue, a Disney Channel Original movie in which she played a high schooler who launches an investigation into a teacher's disappearance.

Freaky Friday

Lohan co-starred with Jamie Lee Curtis in 2003's update of Freaky Friday, which was largely praised by critics. The New York Times marveled: "Loud but never coarse, candid without being prurient, 'Freaky Friday' ... is a quick-witted, perfectly modulated family farce with a pair of beautifully matched performances from Ms. Lohan and especially Ms. Curtis, who does some of her best work ever."

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Confessions of a Teenage Drama Queen

Lohan headlined 2004's critically panned Confessions of a Teenage Drama Queen, in which she portrayed an aspiring Broadway star whose life is turned upside-down when her family moves from New York City to New Jersey. Megan Fox played her high-school rival and Alison Pill her best friend. That same year, she also released her platinum-selling debut album, Speak.

Mean Girls

With a starring role in the Tina Fey-penned Mean Girls, Lohan soared into another stratosphere of celebrity. It was her second time working with director Mark Waters (Freaky Friday), and both a critical and commercial success, grossing $129 million at the worldwide box office. In Slate's review of the film, critic David Edelstein wrote that Lohan "has a natural, redheaded Irish-American prettiness that's a nice contrast to these wiggly Barbie dolls." Lohan scored several MTV Movie and Teen Choice awards for her Mean Girls work.

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Herbie Fully Loaded

Following her Mean Girls success, Lohan starred in Disney's Herbie Fully Loaded (2005) as a VW-bug-driving teen with NASCAR ambitions. While the film garnered mixed reviews, Lohan won favorite actress at the Kids Choice Awards the same year Herbie opened. At the same time, her personal life began unraveling in the public eye: she was hospitalized with a kidney infection during Herbie's shoot, and reportedly, a stressful breakup with actor Wilmer Valderrama was partly to blame. Also, in 2005, her famously spotlight-seeking parents legally separated.

Bobby

Lohan ventured into "serious" film fare with the Emilio Estevez-directed period drama Bobby, an all-star production for which she -- along with the cast -- was nominated for a SAG award.

Just My Luck

Lohan co-starred with Chris Pine in the 2006 rom-com Just My Luck, which attracted negative reviews and also scored Lohan a Razzie nomination for worst actress (despite the industry's general sentiment that Lohan was -- and still is, by some accounts -- a very good one).

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A Prairie Home Companion

Lindsay Lohan plus Robert Altman equals "good career move." In 2006, Lohan was tabloid fodder for her tumultous personal life, brushes with the paparazzi and TMZ-ready relationship with her parents, Dina and Michael Lohan. But in the ensemble comedy A Prairie Home Companion, she got to share the spotlight with the likes of Meryl Streep, who praised the troubled actress in an interview with W magazine, saying: "Lindsay knew her lines better than we did. ... I'm aware of the tabloid stuff because my kids tell me -- but I don't read it, and frankly, I couldn't care less. When they say 'Action,' Lindsay is completely, visibly living in front of the camera ... ."

Georgia Rule

Lohan referenced her wild-child reputation as the wayward daughter of Felicity Huffman and granddaughter of Jane Fonda in the 2007 drama Georgia Rule, which was overwhelmingly bashed by critics. During filming, the then-20-year-old was hospitalized because she was "overheated and dehydrated," her rep said at the time, amid reports of her partying. Lohan's on-set behavior and late arrivals resulted in a scathing letter by Morgan Creek Productions CEO James G. Robinson, who sniped: "You have acted like a spoiled child and in so doing have alienated many of your co-workers and endangered the quality of this picture."

I Know Who Killed Me

Lohan bombed big-time in 2007's I Know Who Killed Me, in which she played a stripper. (She won two Razzies for the role.) That same year, Lohan checked into rehab, was arrested for DUI, checked into rehab again, was arrested for DUI and felony cocaine possession, checked back into rehab for a third time, and served 84 minutes in jail. “It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs," she said in a statement.

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Chapter 27

In 2008's Chapter 27, which was filmed two years before but had troubles landing a distributor, Lohan portrayed a John Lennon fan who becomes friendly with the Beatles icon's killer, Mark David Chapman (Jared Leto).

Labor Pains

In the 2009 ABC Family movie Labor Pains, the actress portrayed a secretary who fakes her pregnancy to avoid getting fired. Lohan "became famous as a Disney heroine in hits like 'The Parent Trap' and 'Freaky Friday,' but this is not a triumphant return of a prodigal child star. She too often looks tired and ill at ease in a role that calls for an engaging, charismatic performance," wrote critic Alessandra Stanley in her New York Times review.

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Machete

Lohan co-starred alongside Robert De Niro and Jessica Alba in Robert Rodriguez's 2010 action film Machete, for which she did no promotion due to her legal issues. This time, Alba picked up a Razzie award, for worst supporting actress.

More Drama

Lohan's personal problems all but eclipsed her once-promising acting career as she began blowing off court-ordered substance abuse treatment courses related to her previous arrests as well as a DUI progress hearing in May 2010 (her reason for absence: she was at the Cannes Film Festival promoting her role in a Linda Lovelace biopic, for which she was ultimately never cast). Several months later, Lohan (known as LiLo in the press) was sentenced to 90 days behind bars and another stint in rehab. Soon after that, in September 2010, she failed another drug test and checked into Betty Ford for several months. In a Vanity Fair cover profile that year, she declared: "I want my career back."

Lindsay and the Necklace

Weeks after leaving Betty Ford, Lohan ran into more trouble in February 2011 when she was charged for stealing a necklace from a Venice Beach boutique. For her latest offense, she served more than a month under house arrest, sporting an ankle bracelet. However, she violated probation (again) for not completing the required 480 hours of court-ordered community service related to her misdemeanor theft and probation violation -- alas, she was sent back to jail, but only for about five hours because of overcrowding.

Lindsay and the Necklace, Part Two

After successfully completing her community service and therapy treatment, Lohan was released from supervised probation in March 2012; however, she'll be on informal probation through March 2014, stemming from the necklace theft. In early 2012, she returned to host Saturday Night Live, made a cameo on Fox's Glee and also appeared on the cover of Playboy in a Marilyn Monroe-inspired pictorial.

Liz & Dick

For her big comeback role, Lohan stars as Elizabeth Taylor in the much-hyped Lifetime movie Liz & Dick. The Hollywood Reporter's TV critic Tim Goodman called the film "spectacularly bad" and Lohan "woeful as Taylor from start to finish. ... It’s an instant classic of unintentional hilarity. Drinking games were made for movies like this."

STORY: Lindsay Lohan on Elizabeth Taylor: 'I Look to Her Because She Got Through It'