The 20 Worst Moments In Lindsay Lohan's Life

Li-Lo's Lows: The 20 Worst Moments In Lindsay Lohan's Life
Lindsay Lohan - what went wrong? From flame-haired hottie in Mean Girls to total trainwreck, these are the moments that got Li-Lo where she is today.

20
Hospitalized For Exhaustion

The first hints of Lohan's future collapse came in 2006, during the filming of Georgia Rule. The young actress had already been the center of some disquieting rumors, but the fact that she had to be hospitalized during the middle of this horrid Garry Marshall child sex drama for "heat exhaustion" tipped people off that something was very wrong in Lohanland. James Robinson, the head of production company Morgan Creek Pictures, sent a letter to Lohan chewing her out for her behavior, saying Lohan had "acted like a spoiled child" and calling her out on her all-night partying.

19
Fractures Wrist

Just months later, Li-Lo would be in the hospital again - this time for fracturing ane of her stick-thin wrists. She had already admitted to Vanity Fair that she was rocking an eating disorder, so it's no suprise that her bone density sucks. During Fasion Week in New York, she toppled to the pavement outside of Milk Studios, and immediately put her lawyers on the case, blaming both the Chanel boots she was wearing and the venue for her lousy balance. Frivolous lawsuit count stands at one.

18
Firecrotch

The first real strike to be thrown against Lohan in the public eye - remember, in the early 2000s she was still riding high on Mean Girls - came from celebutard Brandon Davis, grandson of 20th Century Fox owner Marvin Davis. Davis, notable for nothing but being a fat sack of crap, drunkenly unleashed a tirade on Lindsay to TMZ paparazzi, including dubbing the starlet "Firecrotch" as Paris Hilton looked on giggling.

17
First Time In Rehab

After all the talk of "exhaustion" and mom Dina Lohan claiming that Lindsay just went to AA meetings to "keep her friends company," the starlet finally went to rehab for the first time on January 18 of 2007. Despite an interview with People the week before claiming that she hadn't had a drink in a week, Lohan was wrecked when she checked into the Wonderland rehab clinic. Her presence there was so disruptive that other patients left in disgust. Li-Lo would check herself out not long after.

16
DUI Arrest

And here we go. On May 26, 2007, Lohan was arrested on suspicion of driving under the influence of alcohol. Lindsay was driving her sweet Mecedes convertible at about 5:30 in the morning in LA when she lost control and smashed into some trees. Cops found cocaine in the car, but Lindsay wasn't booked because she was taken to the hospital to investigate "chest injuries." No, not the funbags! Three days later, she went back into rehab, having dodged the bullet of the law... this time.

15
DUI Again, Plus Jail

So Lindsay checked herself out of rehab a few months later, feeling great about the world. And immediately started to drink and do drugs again, once more getting busted by the po-po after a sub-O.J. car chase to discover that she was once again tanked, despite the presence of an alcohol-detecting SCRAM bracelet on her ankle. And, once again, there was coke in the car. Lindsay was also chasing her mother's former assistant, who had recently quit. In August, she copped a plea and got 84 minutes in jail, plus rehab, community service and probation.

14
I Know Who Killed Me Bombs

Just a few days after her arrest, Lindsay's latest movie hit theatres - the dark thriller I Know Who Killed Me was billed as a truly adult role for the young starlet. Unfortunately, it also was a hilarious mess that featured Lohan playing a stripper who never took her clothes off, who then lost a leg and had one of the most unerotic sex scenes of all time. The climax of this movie (which I saw in theatres) was so unintentionally funny I expected it to show up on MST3K. It has an 8% ranking on Rotten Tomatoes, was nominated for eight Razzies (won seven of them, beaten out only by Eddie Murphy in Norbit) and Richard Roeper called it the worst film of the entire decade. So much for the comeback.

13
Stealing Clothes

Lindsay lay low for the next few months, understandably, but don't think that she learned anything from all of her travails. In January of 2008, Lohan attended a party at 1Oak for rich scumbag Stavros Niarchos. Also attending the party was Columbia co-ed Masha Markova, who dressed up for the occasion with a blonde mink coat that had been handed down from her grandmother. Markova set her coat in a check box, but when she got up to leave an hour later, it was gone. Two weeks later, she opened up a magazine to see Lindsay wearing her coat. One lawsuit threat later, the coat was returned reeking of cigarettes but none the worse for wear.

12
Dissed By Obama

All sorts of celebrities got involved with the 2008 Presidential election - after two terms of Bush, people had a lot to say, and the vast majority of them threw their muscle behind Barack Obama. La Lohan was one such celeb, but let's just say the response from Obama's camp was a little chilly. After the starlet offered her help bringing Barack's message to younger voters, campaign staff gently rebuffed her before leaking the whole thing to the press with the comment that Lindsay "is not exactly the kind of high-profile star who would be positive for us." Lohan then proceeded to call Barack America's "first Colored President" in a post-election interview. Oy.

11
Sues E-Trade

Now we're getting into the hot and heavy humilation. Financial services company E-Trade ran a Super Bowl ad in 2009 that featured its trademark talking babies. At one point, the line "that milkaholic Lindsay" was mentioned. Of course, because Lindsay Lohan is the only human being on Earth to ever be named Lindsay, this activated the crazy centers in her brain and she proceeded to sue E-Trade for $100,000,000 for "defamation of character." Unfortunately for Li-Lo, a reporter for Esquire was embedded at E-Trade when the ad was conceived, so he could testify that her name wasn't even mentioned and she was laughed out of court.

10
Labor Pains Straight To Cable

So after all the rehab drama, Lohan took a little time to get clean before getting back into the thick of things in Hollywood. Her first movie after drying up was Labor Pains, an inoffensive comedy also starring Chris Parnell and Cheryl Hines. Unfortunately for everybody involved, Lohan was regarded as such box office poison that the the studio decided to cut their losses and dump the film right to TV - to ABC Family, no less. This basically instantly scuppered Lohan's chance at a comeback in one instant.

9
Ungaro Collection Flops

Fashion house Emanuel Ungaro was pretty depserate by the end of 2009 - how else to explain their decision to hire Lindsay Lohan as "artistic advisor." Nobody was really sure exactly what that meant, but the end result was an absolute disaster. When the line was first shown at Paris Fashion Week, the response from the crowd was disgust and horror. The Times described it as "akin to a McDonald’s fry cook taking the reins of a three-star Michelin restaurant." Needless to say, all of Lindsay's sketches for next season were quickly thrown in the trash and she was sent packing.

8
Coke In The Bathroom

So Lindsay was playing the good girl, tipping off paparazzi to show up on set when she was working to prove that she'd left all of her party days behind her. And then, well, some video hit the Internet that pictured Lohan in a bathroom at a party with Brandon Davis (yes, the Firecrotch guy), indulging in a little Peruvian marching powder. Of course, she denied it was her and tried to blame it on her father Michael, who was at the time releasing taped phone conversations between the pair.

7
Removed From Mean Girls

For some inexplicable reason, 2010 saw the release of a Mean Girls video game. If you don't remember, that film was Lohan's real breakthrough - not only was she charming and likable in the high school flick, she also looked smokin' hot. It didn't hurt that the movie was written by Tina Fey. So you'd think that Lindsay, being the star of the movie, would be on the box for the game, right? Wrong. The box cover features lesser-billed co-stars Amanda Seyfried, Rachel McAdams and Lacey Chabert, but Li-Lo is nowhere to be seen.

6
Intervention

It was only a matter of time before somebody staged an intervention on Lindsay. After the collapse of her relationship with Samantha Ronson (which I'm not even touching on here), she was talispinning heavily with no signs of letting up. So leave it to her hilarious estranged father Michael - a horrendous attention whore in his own right - to barge into her apartment with a group of police officers to check both Lindsay and her weird Progeria sister Ali for signs of drugging. Amazingly enough, both girls are clean, and Lindsay takes to Twitter to bitch about her dad - a three-time felon, let's not forget - invading her privacy.

5
Fired From The Other Side

It's not going to come as any surprise to hear that Lindsay's career was on the rocks after these last few troubles, but it was still painful to hear someone actually come out and say it. Lohan was attached to David Michaels' comedy-adventure The Other Side (now called M) until the producers realized that she was simply just not bankable anymore. She was replaced by Olivia Thirlby, but this was Lohan's last shot at a decent role for some time.

4
Back To Jail

So for quite some time Lindsay has been accessorizing with a SCRAM bracelet, that nifty bit of technology that measures alcohol in the wearer's bloodstream through perspiration. Unfortunately, at the MTV Movie Awards, the thing went bananas because Li-Lo was chooglin' like the old days. Mother Dina Lohan claimed that somebody "spilled a drink" on it, but a judge saw it another way and sentenced Lindsay to ninety days in jail (she served 14) and ninety in rehab (she was there for 23).

3
F--- You Nails

So one would think that if you were heading into a parole review hearing after a life of debauched brat behavior, you'd try to be a little, I dunno, nice? Not Li-Lo - in her hearing with Judge Marsha Revel, she turned up with "F--- You" written on the nail of her middle finger. Except she put the uck in. Lohan claimed that it wasn't directed at the judge - in a Tweet later on, she claimed it was "done as a joke" and it was an "airbrush design with a stencil." Yeah I dunno what nail salon will do that one for you.

2
Underground Comedy

How low has Lindsay Lohan's career fallen? Her only upcoming role is in a little something called Underground Comedy. It's a sketch comedy movie originally directed in 1999 by Vince Offer - you know, the ShamWow guy. It features such scenes of cinematic brilliance as Offer playing a superhero named "Dickman." Offer shot new scenes with Li-Lo last year and plans to re-release the movie - which also stars Joey Buttafuoco and Anna Nicole Smith - this year. And that's it. Nothing in production. No roles on the table. Lohan is now officially box office poison.

1
Felony Grand Theft

And here we are. In January, Lohan walked out of jewelry store Kamofie & Company in Venice, California with a $2,500 necklace. Unfortunately, she didn't pay $2,500 for it. The store decided to press charges, and Lohan's defense - that the store gave it to her in exchange for publicity - isn't holding much water. She's pleading not guilty but her lawyer is trying to get her to cop a plea. Whatever the outcome, she's definitely going back to jail. What is it going to take to scare Lindsay Lohan straight (no pun intended)? The world may never know.

UGO