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Jail sentence (2010)
The latest snag in what was once a young actress' promising career came when a teary Lohan was sentenced to 90 days in jail, starting July 20, for violating the terms of her probation. The ruling came at a time when the 24-year-old was arguably on the path to a comeback, following a few disappointing projects (more on those later). As a result, her work on the Linda Lovelace biopic Inferno and her participation in the promotion for Robert Rodriguez's Machete are — much like her possible return to glory — delayed. But just how did a teen movie queen end up jail-bound? For the answer, perhaps we need to start at the beginning?
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The Parent Trap (1998)
Lohan first charmed America at the tender age of 12, when the fresh-faced redhead tackled a remake of The Parent Trap, about two girls who meet at summer camp only to find they're long-lost twin sisters. The dual roles required a passable British accent, a killer smile, and a whole lot of that patented Disney-brand child-star moxie.
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Freaky Friday (2003)
LiLo's upward trajectory continued with another Disney remake, this time of the classic ''mother and daughter swap places, hilarity ensues'' comedy Freaky Friday. One could do worse than learn at the feet of Jamie Lee Curtis.
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Hilary Duff-Aaron Carter love triangle (2003-2004)
What's more embarrassing — publicly feuding with Hilary Duff over a love triangle with Aaron Carter, or the fact that they were fighting over Aaron Carter?
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Music career (2004-2005)
She better hold off on adding those hyphenates to her job description. Lindsay's debut disc, 2004's Speak, proved mildly promising with its catchy mix of bass-heavy, overproduced pop (imagine Duff and vintage Britney's musical love child). Even the Jake Nava-directed video for first single ''Rumors'' was pretty hot, packed with paparazzi, cage dancing, and cleavage. But 2005's A Little More Personal (Raw) was a sagging, hastily constructed mess. ''Confessions of a Broken Heart (Daughter to Father)''? We'll hold out for the VH1 special.
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Mean Girls (2004)
In her first non-Disney feature film (undoubtedly the troubled starlet's peak performance), Lindsay starred as Cady Heron, a formerly home-schooled good girl-gone-Plastic. Far surpassing expectations, the Tina Fey-penned project opened at No. 1 at the box office, grossing just shy of $25 million in its first weekend, and saw Lohan's fame skyrocket. Smile for the camera, Linds!
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Saturday Night Live host (2004, 2005, 2006)
Remember when Lohan was delivering punchlines instead of, you know, being one? The actress hosted her first SNL in '04 to support Mean Girls' release, and has returned twice since then. Of her many choice skits, the portrayal of a newly busty Hermione Granger stands out for some reason...
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A Prairie Home Companion (2006)
In Robert Altman's final bow, Lohan proved she could tackle drama as she held her own alongside heavyweights Meryl Streep, Kevin Kline, Lily Tomlin, and more.
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Vanity Fair interview (2006)
In her 2006 interview with Vanity Fair, Lindsay came kinda-sorta clean about her troubles, admitting to some drug use and, according to VF, ''bulimic episodes.'' According to the magazine, when she hosted SNL in May 2005, Mean Girls costars Tina Fey and Amy Poehler confronted her about her weight, but only after she saw herself on the broadcast did she realize she had a problem. After confessing that she had used drugs ''a little,'' the actress denied using cocaine, saying, ''It's a sore subject. I've lost a family member over it, practically.'' After the issue came out, a defensive Lohan claimed the magazine misconstrued her words; she denied having an eating disorder.
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Georgia Rule (2007)
Things started off poorly for Lohan after she was publicly chastised by the CEO of Georgia Rule's production company for ''irresponsible and unprofessional'' behavior on set (this was during her rebellious teenage party-girl phase), but got worse when the film's reviews lambasted her acting skills. For playing a rebellious teenage party girl.
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Dakota Moss (Lindsay Lohan)
I Know Who Killed Me (2007)
Again with the dual roles, this time as a hardworking student and her separated-at-birth one-legged stripper twin. Yeah. We didn't even include a spoiler alert there in the hopes of saving you from your own morbid curiosity. As Michael Slezak put it, ''I Know Who Killed Me is 105 minutes of your life you will never get back.''
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Mug shot (2007)
Lindsay's professionally bumpy 2007 saw personal troubles, too — after leaving the Wonderland rehab facility in mid-February, the actress was soon spotted partying at clubs in Los Angeles and New York. On May 26, 2007, she crashed her car, only to be escorted to the Promises Treatment Center in Malibu two days later. A second DUI occurred in late July when Lohan chased the mother of her former personal assistant to a parking lot a block away from the police department. That August, the actress entered her third (and hopefully last) rehab, this time at the Cirque Lodge treatment center in Utah.
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Relationship with Samantha Ronson (2007-2009)
Although their status was often unclear, gossip magazines were buzzing after the pair were caught canoodling on Sean Combs' yacht in May 2008. Their relationship was perpetually rocky — witness the infamous ''I am so alone'' Us Weekly cover — but the ''maybe/maybe not'' lovebirds are no longer as friendly as they once were.
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New York magazine (2008)
In February of 2008, photographer Bert Stern chose Lohan as his muse for a remake of Marilyn Monroe's classic photo shoot ''The Last Sitting.'' The New York magazine spread featured Lindsay posing nude, mimicking Monroe's final shots before her fatal drug overdose six weeks later. On the set, Lindsay referred to the icon's suicide and Heath Ledger's then-recent death as ''tragic'' and ''prime examples of what this industry can do to someone.'' When asked if she was concerned about her own fate, she said: ''I'm not them. But I sure as hell wouldn't let it happen to me.''
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Ugly Betty (2008)
Following '07's box office bombs, Lindsay rebounded with a four-episode arc on the ABC hit Ugly Betty. The actress played Kimmie Keegan, Betty's (America Ferrera) former high school enemy-turned-boss at the restaurant where Betty's father works. Originally scheduled for six episodes, Lohan ended her stint early. While reports surfaced that the cut was due to bizarre behavior and a duel with Ferrera, Betty costar Becki Newton told MTV the allegations were false, and that working with Lindsay was, in fact, ''a great experience.''
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Fornarina commercial (2009)
A girl's gotta pay her mounting legal bills somehow, but here's some advice for Linds from our own Leah Greenblatt regarding this low-budget commercial for Italian clothing company Fornarina: ''Jacking your wardrobe from Sunset Boulevard Barbie and bleating 'Crash! Glam! Pink! Heart! Wow!' like the hostess of a cable-access show for Seussical martian toddlers just makes everyone uncomfortable.''
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eHarmony spoof (2009)
After Us Weekly printed a Lohan cover story that detailed her breakup with Samantha Ronson, the actress made a clever eHarmony spoof for Funny or Die: ''The perfect mate loves long walks on the beach, car chases on the PCH, antiquing, and, uh, passing out in Cadillac Escalades.'' The actress revisited her comedy skills while addressing incessant tabloid coverage and her unfortunate public image. ''So if you think you can handle a redhead with a little sass, and by that I mean a redhead that's...crazy.'' Oh, we can manage that. Keep it coming, girl.
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Sevin Nyne tanning mist (2009)
So, what's an actress to do when movie producers are hesitant to hire her? Perhaps she could roll out a line of leggings (oh, wait...she did). Or come up with the perfect formula for spray-on self-tanner? Genius! In May, Ms. Lohan released her Sevin Nyne (a play on the star's ''lucky'' numbers) tanning mist, available at Sephora for $35. In order to come up with the perfect bronzer, Lindsay worked with ''tanning expert'' Lorit Simon to produce the concoction of goji berry and chardonnay extracts. You can't make this stuff up.