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Lindsay Lohan's career of wrong turns

By Todd Leopold, CNN
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Lohan allegedly calls judge curse word
  • Lindsay Lohan sentenced to jail, rehab on Tuesday
  • Lohan was once considered promising actress, earned raves in box office hits
  • Actress had rough home life; father served jail time, parents fought
  • Lohan has had support from co-stars, director of new film standing behind her

(CNN) -- There was a time when Lindsay Lohan was considered one of the most promising actresses of her generation.

No, really.

In 2006, The New York Times ran a profile of her at 19, and she was already a veteran of good reviews and good box office for "The Parent Trap" (1998), "Freaky Friday" (2003) and "Mean Girls" (2004).

In her future, the article said, was the Robert Altman film "A Prairie Home Companion," the drama "Bobby" about Robert Kennedy and "Chapter 27" about John Lennon killer Mark David Chapman. She was taking serious roles and changing her career path after a handful of teen-targeted Disney projects.

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The flip side of Lindsay Lohan, however, was also painfully obvious. The article was headlined, "Lindsay Lohan: Portrait of the Party Girl as a Young Artist."

The "party girl," who turned 24 last week, is now at another crossroads. On Tuesday, a judge sentenced her to 90 days in jail and 90 days in a drug and alcohol rehab program. The sentence comes after months of tabloid mockery, poor behavior and romantic struggles -- all for public consumption.

"It's amazing to realize that Lindsay's only 24 years old. She's already been to rehab three times, she's already been to jail before, she's faced two DUI arrests -- it's amazing the amount of life she's lived in a short amount of time," says Us Weekly's Lindsay Powers, who has covered Lohan and interviewed her parents.

How did Lohan get here?

Part of it's the story of a sweet, talented kid gone awry, says media expert Howard Bragman of Fifteen Minutes media and public relations agency.

"As a young actor, she was incredibly appealing, and she became more appealing," he says. "She was gawky and freckly, and she grew up into a beautiful young woman, and we enjoy watching that."

And part of it is the related story of too much too soon, observes Powers.

"She had a lot of fame, access and notoriety from a very young age. She also does not come from the most stable home environment," Powers says. "Lindsay has never really had a stable background to fall [back] on."

She was born July 2, 1986, in New York City. Almost her entire life has been lived in public: She was modeling by the time she was 3, making TV commercials and appearing on the now-defunct soap "Another World" before she turned 10.

At 11, she was plucked from a group of 4,000 hopefuls for the 1998 remake of "The Parent Trap." Even then, amid the hot air of publicity, it seemed like she had a strong future: "Trap" director Nancy Meyers compared her to a young Diane Keaton in an article in People.

Disney, the "Parent Trap" studio, signed her to a contract, and she appeared in some easily forgotten TV programs: the TV movies "Life-Size" and "Get a Clue," a series pilot with Bette Midler. Then she was tapped for "Freaky Friday," a remake of a 1976 Disney movie. The smartly done comedy surprised critics and pleased audiences. Lohan was on her way.

But her family life has been rocky -- and equally public -- since she became famous.

Her father Michael Lohan, a former securities trader, served several stints in jail: for contempt of court, violating parole, DUI and assault for getting into a fight with his brother-in-law after his son's first communion. In recent years, he says he has found religion.

Lohan's mother, Dina, a former singer and dancer, topped a "crazy moms" list conducted by the gossip site and parlayed her daughter's notoriety into a reality series, "Living Lohan," with Lindsay's sister Ali. Michael and Dina separated twice and divorced in 2007.

Other adults have taken a guiding interest in her. Co-star Tina Fey praised her during the making of "Mean Girls." "Prairie Home" co-star Meryl Streep was quick to defend her in a 2006 interview with W magazine.

"She's very young. It's a great sort of coin to have, a wonderful time in somebody's life. 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," she said. "When they say 'action,' Lindsay is completely, visibly living in front of the camera, and that's all anybody really cares about."

Even her latest director, Matthew Wilder, has stood up for her.

"I am 100 percent behind Lindsay and can say the same for everyone involved in the production of 'Inferno: A Linda Lovelace Story,' " he told MTV News, characterizing Lohan as someone "who is really different from the cartoon portrayed in the tabloid press."

But it hasn't been enough, says Powers.

"She definitely has had a lot of opportunities for role models ... but the thing is, she tends to be surrounded by people who are enablers, who are also in the limelight, that may not have the best intentions," she says.

The tabloids and gossip blogs have found much to feast on since Lohan became a teenager.

She's been criticized for her weight, both when she's alleged to be too heavy or too thin. Her every romance has been scrutinized, from a liaison with teen heartthrob Aaron Carter (who also dated Disney colleague Hilary Duff, leading to an alleged rift between Lohan and Duff), to a very public relationship with DJ Samantha Ronson. And Lindsay used her Twitter account to post a topless photo of herself.

"Her behavior has just been a gift to the blogosphere and the tabloids in the kind of world we live in," says Bragman, who says that Lohan appears addicted to the attention. "We live in a very, very transparent world ... and she seems to be in front of it."

For all this, though, there's still hope Lohan can turn her life around, says Powers. She points to Robert Downey Jr., another talented performer who had some horrific times, as an example. "There's somebody that really hit rock bottom, and now, with age and maturity, was able to bounce back," she says.

But first, says Bragman, Lohan has to be honest with herself. Jail and rehab may help -- or it may not.

"There certainly is a problem of some sort or another, if only her inability to acknowledge that there's problems," he says. "Nobody can go to rehab from anything without acknowledging there's a problem."