Lindsay Lohan: From Promising Actress to Box Office Babe to Jail

In 1998, Lohan made her big screen debut in the dual role of Hallie Parker and Annie James in 'The Parent Trap,' an update of the 1961 Hayley Mills vehicle. The cute redhead charmed audiences and held her own against veterans Natasha Richardson and Dennis Quaid. The movie earned her the Young Artist Award in 1999.

After 'Trap,' Lohan appeared in two made-for-TV movies on the Disney Channel -- 'Life Size' and 'Get a Clue' -- in 2000.

Meanwhile, she began dating Aaron Carter. The little brother of Backstreet Boy Nick, Aaron started a rift between Lindsay and fellow Disney tween star Hilary Duff, who also dated Carter around the same time. The feud between the two escalated and lasted for years before Duff finally declared "it's over."

She returned to the big screen in 2003 for 'Freaky Friday,' another remake of a Disney classic. The film was a big hit for the young actress, and she was named Breakthrough Female at the 2004 MTV Movie Awards.

However, it was 2004's 'Mean Girls' that propelled Lohan to true superstardom. The film was a box office hit, earning over $86 million made domestically, and proved that its star had stellar talent and impeccable comedic timing. Lohan again prevailed at the MTV Movie Awards in 2005, taking home the trophies for Best Female Performance and Best On-Screen Team with her co-stars.

While filming her next venture, 'Herbie: Fully Loaded,' Lohan recorded and released her first album, 'Speak.' The set went platinum in 2005.

The production of 'Herbie' -- released in theaters in 2005 -- was halted when Lohan experienced medical issues (she was hospitalized with a kidney infection) and was plagued by her personal drama (she'd recently broken up with boyfriend Wilmer Valderama). But the film was a moderate success, grossing $144 million worldwide.

It was during 'Herbie' that Lohan's off-screen antics truly began affecting her professional life. Stepping out with Nicole Richie in May 2005, the two caused a stir with their very thin frames. In place of her trademark 'Mean Girl' curves was a near-skeletal physique.

Lohan's family only added to her drama. Her relationship with Michael Lohan has long been contentious -- she even released a music video, titled 'Confessions of a Broken Heart,' chronicling their issues. More recently, Michael, who was arrested in 2005 for DUI, tried to force his daughter into rehab, something she tweeted furiously about. And although Lindsay and her father remain estranged, he appealed to judge Marsha Revel to keep his daughter from jail.

Meanwhile, her first big paycheck following her 'Mean Girls' success came in the 2006 film 'Just My Luck,' which received a 12 percent rating on Rotten Tomatoes and only made $17 million at the box office. Later that year, however, she starred in critical indie darlings 'A Prairie Home Companion' and 'Bobby.'

Lohan continued to struggle with her weight, and in 2006 appeared on the cover of Vanity Fair, purportedly admitted to bulimia. "I was sick. Everyone was scared. And I was scared too. I had people sit me down and say, 'You're going to die if you don't take care of yourself,'" she said in the interview.

However, the actress later claimed she was misquoted. But the year only continued to spiral for the starlet. During filming of the box office and critical bomb 'Georgia Rule,' she was hospitalized for exhaustion and received a scolding letter from producers.

"You and your representatives have told us that your various late arrivals and absences from the set have been the result of illness; today we were told it was 'heat exhaustion.' We are well aware that your ongoing all night heavy partying is the real reason for your so called 'exhaustion.' We refuse to accept bogus excuses for your behavior," the letter read.


The party continued for the rest of the year, with paparazzi following her every move. On November 27, 2006, photogs snapped her in Paris Hilton's car, alongside Spears, in Beverly Hills. Hilton and Lohan had just gotten over their feud, which was sparked by Lindsay's canoodling with Paris' ex, Stavros Niarchos.

Only a few days later, her rep admitted that Lohan was attending Alcoholics Anonymous meetings. But those clearly weren't enough, and in January 2007, she began her first stint in rehab. At the time, she was filming 'I Know Who Killed Me' and production had to be halted.

Later that year, in May, she entered rehab again. She would eventually seek treatment for a third time in early 2007, following two DUIs, the second of which was the catalyst for her 90-day jail sentence.

Although Lindsay has dated a string of men -- from Harry Morton to Jared Leto to Calum Best -- in 2008, she started dating Samantha Ronson. The two would fight, break up and get back together via their Twitter accounts. Michael Lohan went so far as to cite Ronson as the reason Lohan was having problems.

In a surprisingly candid interview with British paper The Sun, Lindsay revealed details of her relationship with Ronson as well as her drug use.

"I never really thought about women before, it kind of just happened with Samantha. It surprised me," Lindsay says. "If I wasn't with Samantha, I would probably be with a boy next. She's the only woman I've been attracted to. We love each other. We might reconcile the relationship, maybe. I don't know," she described.

"When my father was going public, that's when I hit rock bottom. I abused substances too much and it wasn't the answer to my problems. People need to know that," she recalled of her 2007 stints in rehab and troubles with her father.

It seems apparent that Lindsay's decline was gradual. What began with drama over a boy escalated into weight and possible eating disorder problems, and when combined with family troubles, the constant pressure of the paparazzi and her unhealthy relationship with Samantha Ronson, it's easy to see how Lindsay never really got her feet firmly back on the ground.

In our mind, the tipping point where her career took a backseat to her drama was 'I Know Who Killed Me.' The movie garnered an 8 percent rating on Rotten Tomatoes and grossed only $7.5 million at the box office. Appropriately enough, she played a dual role in this film, which brought her career full circle from 'The Parent Trap.' Yes, she's filmed things since then -- a stint on 'Ugly Betty,' from which she was allegedly fired, and 'Labor Pains,' which ended up going straight to TV -- but she hasn't been seen in a big screen hit in a long time.

She has a promising role in 'Machete' coming up, as well as the Linda Lovelace film 'Inferno,' which could also be her career savior. For her sake -- and ours -- we hope she can pull herself up and regain some of her former glory.

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