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Fights over guys
Years before Team Angie vs. Team Jen, it was Team Lindsay vs. Team Hilary. In 2002, Lohan fought with Duff over Aaron Carter, who couldn't seem to choose between the stars. Two years later, Lohan took up arms again when she fought with Ashlee Simpson over Wilmer Valderrama (a feud which inspired Simpson's hit single "Boyfriend").
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Not picture perfect
Lohan wasn't so picture perfect when she and bud Vanessa Minnillo posed provocatively holding knives to each other in 2007. The actress once again became the center of controversy in 2012 after Terry Richardson photographed Lohan with a handgun with images meant to evoke suicide.
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When it all started
2007 was one never-ending scandal for the troubled star. Throughout the year, Lohan was admitted into rehabilitation centers three separate times, got fitted for her first SCRAM bracelet and crashed her Mercedes. But that's not all, folks! She was also charged with two DUIs, possession of cocaine and driving under a suspended license. After all that, Lohan received three years probation and served only 84 minutes in jail due to "overcrowding."
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A letter of note
Lohan claimed her hospitalization during the filming of George Rule was from heat exhaustion, but studio exec James G. Robinson wasn't buying it. In a leaked letter, Robinson blamed Lohan's heavy partying on her "illnesses" and called her various absences from set "irresponsible and unprofessional." "You have acted like a spoiled child," Robinson added, before implying the actress would be held financially accountable for any losses the film sustained.
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A bitter breakup
Lohan's relationship with Samantha Ronson came as quite a shock to many, but not nearly as much the details of its fiery demise. Lohan didn't seem to have any qualms airing the pair's dirty laundry on Twitter, using the platform to accuse Ronson of cheating, using drugs, calling her gross and claiming Ronson's family of controls her. Ronson, on the other hand, preferred to stay out of the fray with the exception of once tweeting her ex, "I'll only follow [you on Twitter] if you're starting a cult driven mass suicide." Ouch!
6 of 17 Bert Stern for New York Magazine
Though Lohan has admitted she greatly relates to Elizabeth Taylor, it's clear Marilyn Monroe is her true idol. The actress recreated Marilyn Monroe's infamous "The Last Sitting" photo series with the original photographer Bert Stern. But Monroe fans' displeasure at the tribute didn't stop Lohan from paying homage to the icon countless more times (often wearing little-to-no clothes).
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During the 2008 presidential election, Democratic nominee Barack Obama declined Lohan's offer to help his campaign, explaining how Lohan "is not exactly the kind of high-profile star who would be a positive for us." That didn't stop her from sharing her support of Obama on her MySpace. During Obama's 2012 re-election campaign, Lohan switched sides, supporting Republican nominee Mitt Romney.
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In 2009, her dad Michael Lohan sold tapes of phone calls between himself, Lindsay and her mother Dina to the media. In one tape, the actress can be heard hysterically sobbing, and complaining about problems with her family and ex-girlfriend Sam Ronson. “No one cares about me. They don’t, by the way," Lindsay cried.
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After missing a probation hearing while promoting Inferno in Cannes, Lohan eventually ended up back in rehab. Turns out all that drama (which included a warrant issued for her arrest), was all for nothing. While Lohan was in the Betty Ford Center, director Matthew Wilder dropped the actress and later replaced her with Amanda Seyfried. That wasn't the only time LiLo has been tossed aside. The actress was also dropped from The Other Side and Gotti: Three Generations.
10 of 17 ETrade
What's in a name?
In 2010, E-Trade released a commercial featuring babies talking about a "milkaholic" named Lindsay. Believing herself to be the basis of the joke, Lohan sued the bank for $100 million, claiming it violated her rights. The parties settled privately, but Lohan reportedly made some money out of the suit.
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Talk about crocodile tears! While LiLo was tearfully pleading for leniency at her probation hearing, her fingernail told another story. During the hearing (at which Lohan was sentenced to 90 days in jail), Lohan's manicured middle finger sported quite the explicit message: "F--- U."
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Recovery has never been smooth for Lohan. During her 2010 court-ordered stint at Betty Ford, a clinic employee sued the actress, claiming Lohan physically attacked her. According to the worker, Lohan returned to the clinic visibly intoxicated one night and things got physical when she attempted to administer a breathalyzer to the star. Though Lohan admitted there was a scuffle, she claimed the employee provoked the incident.
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To catch a thief
Only a month after leaving rehab in January 2011, Lohan was once again charged with a felony, this time for allegedly stealing a $2,500 necklace from a Venice Beach, Calif., store. Lohan pleaded no contest and was sentenced to 120 days in jail and 480 hours of community service for violating her DUI probation. The actress served only 35 days of home detention before adding on another 30 days in jail for failing to show up to her community service at the Downtown Women's Center. In typical LiLo fashion, the actress was locked up for only five hours before being released and ordered to complete her hours at the morgue.
14 of 17 Playboy Magazine
Lohan bared all for Playboy's January 2012 issue. Once again taking inspiration from Marilyn Monroe, LiLo's spread help earn record-breaking sales for the magazine (and record-breaking disappointment for many who expected to see the real Lohan and not the heavily Photoshopped one Playboy published).
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Lohan became the top suspect in the theft of $100,000 worth of items from a Hollywood house party the actress attended. Even after the home owner retracted his story, LiLo was reportedly still being investigated for the heist.
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2012 was not a good year for Lohan and cars. Giving Amanda Bynes a run for her money, Lohan's car crash into an 18-wheeler on the Pacific Coast Highway was only the start of her vehicular troubles. Police claim the actress lied about not being behind the wheel and, as a result, her probation could be revoked. The actress was also accused three separate times of hitting pedestrians, including one incident where she was arrested for fleeing the scene.
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Never-ending family drama
In October 2012, Michael Lohan called the cops to his ex-wife's home to investigate a fight between Dina and Lindsay. In a leaked phone call LiLo made to her dad during the incident, Lindsay can be heard saying Dina was on cocaine and "acting like the devil." Lohan later recanted, saying she had lied about her mother and that she was "done" with Michael.