Mean Girl?

Lindsay Lohan: Jail Sentence, Mug Shot, Theft & More Troubles (Photos)

Fresh off ‘Liz and Dick,’ LiLo was arrested … again. A look at the child star turned repeat offender.

The Life and Career of Lindsay Lohan

2012 was supposed to be the year of Lindsay Lohan’s comeback—but it didn’t exactly turn out that way. See a timeline of her troubled life and career, from her fresh-faced starring role in The Parent Trap to her nude Playboy spread to her latest arrest.

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The Parent Trap

Born in New York City on July 2, 1986, Lohan signed on as a Ford model by age 3, and during elementary school acted in commercials for companies including Pizza Hut, Gap, Wendy’s, and Jell-O. In 1998, Lohan appeared in her first film, The Parent Trap, alongside Dennis Quaid and Natasha Richardson. Director Nancy Meyers likened Lohan to a young Diane Keaton. Two Disney made-for-TV movies followed: Life-Size (2000) and Get a Clue (2002).


Freaky Friday

The first of her many romances in the spotlight, Lohan dated singer Aaron Carter from January 2002 to April 2003. After she learned that Carter had taken up with Lizzie McGuire star Hilary Duff at the same time, public badmouthing between the teen stars ensued—and has continued up to this year. (In May, Carter told CNN, of Lohan’s recent legal woes, “She deserves it. I’m not gonna give any sympathy for somebody who makes mistakes. You need to take fault for your own actions in life.”) In 2003, Lohan starred alongside Jamie Lee Curtis in Freaky Friday, earning her an award for breakthrough female performance at the MTV Movie Awards the next year. Everything was coming up roses for LiLo.

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Mean Girls

Things only got better from there: at 17, Lohan starred in the hit movie Mean Girls, which opened at No. 1, grossed more than $129 million worldwide, and is quoted by teen girls to this day. That same year, she also became the youngest-ever host of the MTV Movie Awards; released her debut album, Speak; got into her first car accident (two more would follow); and briefly dated 24-year-old That '70s Show star Wilmer Valderrama. Oh, and during the shooting of Herbie: Fully Loaded, she was hospitalized with a kidney infection due to stress.


Party Time

Lohan gained a party-girl reputation in 2004 and 2005, often going to L.A. clubs with paparazzi favorites Nicole Richie and Paris Hilton. (Not so coincidentally, around the same time, she launched her pop-music career.) “I’m 17. I’m learning, and I’d rather make my own mistakes and learn from them than have to be sheltered my whole life,” Lohan told People magazine in 2004. In 2005, Lohan became the first star to have a Mattel My Scene celebrity doll; released her second album, A Little More Personal (Raw); and was told that her parents were legally separating (the messy divorce was finalized two years later).

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Weighty Issues

Lohan, then 19, showed off a scary-skinny frame in Beverly Hills in May 2005. She later told Vanity Fair: "I knew I had a problem and I couldn't admit it ... My arms were disgusting. I had no arms." She went so far as to say, "I was making myself sick," before claiming her apparent admission of bulimia was  misconstrued." Lohan told Vanity Fair that Saturday Night Live creator Lorne Michaels and star Tina Fey staged an intervention: "[They] sat me down, literally before I was going to do [SNL], and they said, 'You need to take care of yourself. We care about you too much, and we've seen too many people do this, and you're talented,' and I just started bawling."


Driving Under the Influence

In 2006, Lohan started attending Alcoholics Anonymous meetings—which, if her actions the next year were any indication, didn’t help. In January 2007, she underwent an appendectomy and, afterward, checked herself into L.A.’s ritzy Wonderland Center, a celebrity-friendly rehabilitation facility, for a 30-day stay. In May she was in a car accident and arrested with a DUI charge. After being sent to another rehab facility, Lohan was fitted with a SCRAM bracelet to monitor her sobriety. In July she was arrested for a DUI and possession of cocaine. (She pleaded guilty a month later and was sentenced to one day in jail, 10 days of community service, mandatory alcohol-education classes, and three years of probation.) In November, Lohan released the following statement: “It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs.”

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Bisexual? Maybe. Lesbian? No.

In 2008, Lohan began dating disc jockey Samantha Ronson (left)—a relationship that would, as with most things in Lohan’s life, turn volatile. When asked if she was a lesbian, Lohan told Harper’s Bazaar, “I don't want to classify myself. First of all, you never know what’s going to happen—tomorrow, in a month, a year from now, five years from now. I appreciate people, and it doesn’t matter who they are, and I feel blessed to be able to feel comfortable enough with myself that I can say that.” She and Ronson broke it off the next year. Around the same time, Lohan dipped her toes in a new world and released a self-tanning spray called Sevin Nyne.

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The Ungaro Disaster

In September 2009, it was announced that Lohan had been tapped as an artistic adviser for the French fashion house Emanuel Ungaro, most likely a result of her highly publicized shopping habits and enormous closet. Paired with Spanish fashion designer Estrella Archs (left), the two worked in tandem as part of Ungaro’s new “consumer-led” business model. The first joint Lohan-Archs collection made its highly ridiculed and hotly debated debut during Paris Fashion Week in October. By early 2010, it was reported, Lohan had been dropped from the gig.

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Probation Extension

On Oct. 16, 2009, Lohan appeared at a Beverly Hills court for a hearing stemming from her 2007 drunk-driving case. The result: her probation was extended another year. The reason: so she could finish her mandatory alcohol-education program. (At the time, TMZ reported, Lohan had completed only about half of her classes.) If the court had to accommodate Lohan again, the judge warned at the hearing, a jail stint would be in her future. It turns out he was bluffing. After missing checkup hearings in December, February, and May, Lohan’s legal representatives paid 10 percent of a $100,000 bond, avoiding a warrant for her arrest.

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Birthday Punch

Lohan attended the MTV Movie Awards in June last year, despite not being nominated for anything and acting in only one movie that year, the long-forgotten comedy Labor Pains. She notably wore a sparkly floor-length pantsuit to cover up her SCRAM ankle bracelet. Following the ceremony, she attended Katy Perry’s after-party, where the bracelet went off, but Lohan’s lawyer claimed she didn’t consume any alcohol. Several weeks later—on her 24th birthday, no less—a waitress at the L.A. club Voyeur punched Lohan, supposedly over Doug Reinhardt, who she was hanging out with. “A waitress just hit me—punched me for no reason,” she tweeted. It was reported Lohan sipped Red Bulls—without vodka.

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The Nail in the Coffin

Seemingly, the court was not buying it. A judge ruled that Lohan had violated the terms of her probation and sentenced her to 90 days behind bars at a July 6, 2010, probation revocation hearing. The judge also ordered the actress—who had been sporting the words “F--k You” on her fingernail in court—to check into an inpatient rehab program for three months after her release from jail. Soon thereafter, Lohan’s longtime lawyer quit. On July 20 of the same year, the starlet began serving her sentence, which lasted for just 14 days. Lohan was released on Aug. 2 due to a policy of early release of nonviolent offenders to reduce jail overcrowding. Though she was expected to stay at an inpatient rehabilitation facility immediately thereafter for 90 days, Lohan was released after only 23 days because “the treating doctors at UCLA felt she had done everything required of her there.” Lohan continued with mandatory outpatient therapy and was also ordered to submit to random drug and alcohol tests and to attend therapy multiple times per week.

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Can Betty Save Her?

In August 2010, Lohan told Vanity Fair, “I want my career back … I know that I'm a damn good actress, and it’s been my passion since I was a child, and I know that when I care about something, I put 100 percent and more into it.” Though she was back on screen, Lohan was not part of the promotion for Robert Rodriguez’s Mexploitation film Machete, which opened in September 2010. And shortly after its release, her probation was revoked following a failed drug test. Lohan spent part of the day in jail before being released on bail. A few days later, she entered the Betty Ford Center, where she remained on court order for three months until early January 2011. Toward the end of her time, Lohan was sued by a former Betty Ford Center employee, who alleged that Lohan grabbed and twisted her arm when she attempted to give her a breathalyzer test in December. Though Lohan did ring in 2011 in rehab, she was released shortly after the new year.

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Sticky Fingers

She may have been out of drug and alcohol–related trouble, but Lohan wasn’t in the clear. While still on probation in February 2011, Lohan was being investigated for the theft of a $2,500 necklace from a jewelry store. After she was charged, which she claimed was a miscommunication and alleged that she was borrowing the jewelry, Lohan rejected a plea bargain in March. In April she was sentenced to 120 days in jail, 360 hours of community service at the Downtown Women's Center, and 120 hours at the L.A. County morgue for misdemeanor theft and violating her probation. Due to jail overcrowding, Lohan served the sentence under house arrest and wore another SCRAM monitor for most of the month of June. While under house arrest, she failed a random alcohol test, but a judge decided it didn’t warrant any additional punishment.

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Married to the Mob

Things were looking up for Lohan. In April 2011, it was announced that Lohan had signed on to appear opposite John Travolta in the upcoming movie Gotti: Three Generations. She was cast to play Kim Gotti, wife of mobster John Gotti Jr. As of November 2012, however, the project still seemingly hasn't gotten off the ground. 

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Back Behind Bars

On Oct. 19, 2011, a judge revoked Lohan's probation after she missed too many of her community service appointments. The actress was sent to jail for the fifth time in her life with a bail set at $100,000 and ordered to complete 16 hours of community service at a morgue before her next hearing—which she failed to do. At the hearing that followed on Nov. 2, Lohan was sentenced to 30 days in the county jail and 400 hours of community service. 


Three months later, Lohan was reportedly paid $1 million to grace the cover of the January/February issue of Playboy magazine. Baring it all, the once innocent Freaky Friday star channeled Marilyn Monroe in a vintage inspired shoot. A similar spread appeared in the first issue of Playboy where Monroe posed behind a velvety, red backdrop. The original playboy himself, Hugh Hefner, said he had mixed feelings about the Monroe-themed shoot. “I could not have anticipated, quite frankly, that it would turn out to be such a sensational newsworthy event, or that the pictorial would turn out so well.” According to Hefner, the January/February issue of the magazine broke sales records.

2012: Year of the Comeback?

Lohan appeared on the Today Show in February 2012 and spoke with Matt Lauer about the public troubles that have defined her character over the past few years. But at just 25 years old, she claimed a “comeback,” saying she was now clean, sober, and ready to move forward. “I learned how to live my life in a way that I’m happy,” Lohan said. She hosted Saturday Night Live that weekend—and earned mixed reviews. But if nothing else, Lohan's fourth time hosting the show proved she's at least got a sense of humor—she joked about her drug and legal problems during her opening monologue.

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‘Liz and Dick’

In November, Lohan made her long-awaited Lifetime channel debut with Liz and Dick, which was supposed to herald the return of Lindsay the actress. It wasn’t meant to be. Between the corny dialogue, cheesy acting, and Lohan’s apparently frozen face, the film drew scathing reviews—which reportedly “devastated” the starlet. However, as Entertainment Weekly’s Ken Tucker wrote, “there’s still a vulnerable quality to her, the same sensitive-soul aspect to her gaze that’s been there since she starred in The Parent Trap (1998), that keeps one’s hope alive.”

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Rumble Avenue

That “sensitive soul” apparently decked a girl in the face just four days after Liz and Dick aired, however, landing Lindsay, once again, in handcuffs. After attending a Justin Bieber concert at Madison Square Garden, Lilo headed to Chelsea nightclub Avenue with her posse and the boys from The Wanted, who also played that night. Reports indicate that Lohan was trying to cozy up to band member Max George (who reportedly left after being “turned off” by the actress’s drunken state), but ended up getting into an altercation with a psychic named Tiffany Mitchell instead. Mitchell told TMZ that she “had a premonition” about Lohan and offered her a free reading. Lohan refused and asked Mitchell to give her space, then reportedly muttered something about “fucking Gypsies” as Mitchell walked away. A friend of the psychic fired back at Lohan, calling her a “whore” and telling her that “Liz and Dick sucked.” Did the psychic see this coming? Lohan then reportedly punched Mitchell in the eye, prompting an arrest on charges of assault. Adding to her misery, three additional misdemeanor charges against Lohan emerged a few hours later, stemming from a June accident on the Pacific Coast Highway in Santa Monica. The actress was also involved in a police investigation in September after alleging that a man assaulted her in a New York hotel—only two weeks before the tables were turned and another man accused her of bumping into him with her car outside another Manhattan nightclub. Charges were dropped in both cases, but they certainly showed that 2012 was not the comeback year Lohan—and her fans—had hoped for.