In the late nineties and early 2000s, Lindsay Lohan was a favorite among fans and critics. She appeared in popular movies like The Parent Trap, Freaky Friday, and Mean Girls. In these films, she worked with other A-listers, including Jamie Lee Curtis, Rachel McAdams, and more. Unfortunately, stardom and being a target of tabloids eventually got to the star. She released her 2004 song "Rumors" with the chorus, "I'm tired of rumors starting. I'm sick of being followed. I'm tired of people lying, saying what they want about me. Why can't they back up off me? Why can't they let me live?"

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By 2005, rumors spread that she had an eating disorder after a picture of her surfaced online, and by 2006, her partying got out of control. For the next decade, Lindsay had many difficult encounters with law enforcement and she missed many career opportunities. Today, Lindsay Lohan is winning the battle against her addictions and making the right moves for a career comeback.

8 The End Of The Party For Lindsay Lohan

While filming the 2007 comedy drama Georgia Rule, Lindsay was hospitalized for "exhaustion," but a studio executive called her out in the media, saying the term "exhaustion" used by Lohan’s legal team was actually to cover up Lohan's "partying." In 2007, Lindsay entered her first drug rehabilitation program while filming the rated R movie, I Know Who Killed Me. She spent thirty days at a treatment center in Los Angeles. After facing serious legal troubles over the next five years, the starlet entered four additional rehabilitation programs in California and Utah.

7 Lindsay Lohan Against The World

After her first treatment center, arrests, court dates, and more rehab followed. She was arrested twice in the summer of 2007, the first on a misdemeanor driving under the influence (DUI) charge after driving into a curb. The second time, she was arrested for a DUI, drug possession, and driving on a suspended license. A judge sentenced her with a slap on the wrist punishment of only 10 days of community service, a fine, alcohol education courses, and three years' probation. From 2007 to 2012, Lohan had multiple arrest warrants for missing probation meetings, an arrest for a theft charge, jail time (although, she never spent more than four hours in a cell), and appearances in front of a judge.

6 Lindsay Lohan's Dating Life Was Tabloid Fodder

During her 2007 trip to a rehab center in Utah, Lohan met her ex-boyfriend, Riley Giles. He sold his story to the press after their split, calling her a nymphomaniac and a sex addict. He said, "Sex became a key part of her recovery." By 2008, Lohan's relationship with DJ Samantha Ronson made the tabloids as they partied together and kissed in public. They didn’t come out as a couple but admitted in the media that they shared a very special and close bond.

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5 Lindsay Lohan's Questionable Career Choices

Lindsay continued to work and land roles due to her success, but she was still struggling with her past mistakes. A studio executive threatened her with legal action due to her unprofessional behavior. She continued into the 2000s without much success. I Know Who Killed Me received a 9% from critics and 26% from the audience on Rotten Tomatoes. She appeared on the series Ugly Betty, but reports suggest her time on the show was cut short due to tension on set. After appearing in a number of small roles and unsuccessful films, Lohan appeared on the cover of Playboy magazine in 2012.

4 Lindsay Lohan And Sobriety

After multiple probation violations, she was facing 270 days in jail in 2011. Over the next six-week period, Lohan completed all rulings by the judge on time. She continued to get glowing probation reports and in March of the same year, the judge ended Lindsay’s probation. She was arrested for a dispute with a woman in 2012, but as of 2022, she is living sober. She told the Christian Post, "yes, I'm good, and I'm clean and sober now."

3 Lindsay Lohan’s Comeback Roles

Since 2012, Lindsay has landed some roles that would help push her into A-list territory once again. However, her films and appearances have missed the mark. Her 2012 movie, Liz & Dick, received 33% from critics and 19% from the audience on Rotten Tomatoes. One critic said, "Lohan should have shed her protective shell and made an effort to try and understand a psyche other than her own." Her next attempts at a comeback include The Canyons, quoted as "flat and imbecilic," Sick Note has reviews claiming the cast was wasted on bland jokes, and Among the Shadows has a 2.1 rating out of 10 on IMDb. She’s also done some voice work, guest appearances, her own reality show, and a segment on a talk show.

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2 Lindsay Lohan's Reality Shows

In 2014, she appeared in a reality show on the Oprah Network, self-titled Lindsay. It followed Lohan’s recovery process and brought fans a look behind the curtain of the fallen starlet's life. In 2019, Lindsay Lohan had a reality show titled Lindsay Lohan’s Beach Club, which followed her on the Greek Island of Mykonos, where she opened a beach house. It included a restaurant, a boutique, and a beauty spa area. A little less than a year later, her show was canceled, and her company closed down. The space on the island is now deserted without a trace of Lohan’s name or presence.

1 A Lindsay Lohan Netflix Deal

These days, she has just finished filming a new movie for Netflix for the holiday season titled Falling for Christmas. She is also currently in pre-production for the horror film Cursed as Detective Mary Branigan, who is racing against time to save lives. The New York Post reports she’s signed on to a multi-film deal with Netflix, and one executive stated, "We’re so happy with our collaboration with Lindsay to date, and we’re thrilled to continue our partnership with her." Watch out for Lindsay making a strong comeback on the popular streaming service, but it may be best to wait for the reviews before saying she’s ready for the big screen.

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