Underage Drinking: Not a Minor Offense
Mean Girls was undeniably Lindsay's breakout film in Hollywood. She plays a 16-year-old girl named Cady who grows up in South Africa and moves to Evanston, Illinois, where she runs into vicious high-school cliques—including the Plastics. Look, the pressures of high school (what with all the drinking and sex) make people do silly things. But here, in the absence of parental supervision, Lindsay throws a party with underage drinking. Clearly, this was filmed in the pre-SCRAM years.
All Aboard for Public Indecency
In 1998's The Parent Trap, a 12-year-old Lindsay reunites with… another Lindsay. The shenanigans get under way as English Lindsay faces off with American Lindsay in a game of poker. Illegal gambling at camp? That's only a petty crime. A pre-teen skinny dip in the lake, however, is a far more serious matter.
Stripping Killed Your Acting Career
Lindsay's portrayal of Dakota Moss, a stripper who may be a pianist and writer with a bad case of amnesia, in 2008's I Know Who Killed Me was slammed by critics and garnered her a Razzie for worst actress. It was another (and hopefully her last) foray into the world of tackling two roles in one movie. The film did show off one of Lilo's lesser-known talents— pole dancing.
"Rumors" Throw Lindsay Behind Bars
When Lindsay released her debut pop album Speak in 2004, we didn't think she really had anything to say. But on the album's highlight track "Rumors," she spoke to us about, you know, her struggles. "I got to say, respectfully/ I would love it if you took the cameras off of me." That didn't happen. Maybe it was fate or just a poor metaphor, but the following scene of the song features Lindsay behind bars… in a birdcage, but still.
Larceny + Black Magic = Yikes
Don't be fooled by the cute background music in this scene from the 2000 made-for-TV movie Life-Size. In the film, Lindsay attempts to resurrect her mother, only to bring her perfect doll Eve (played by Tyra Banks, naturally) to life. But in order to do so, Lindsay first snoops around on a mysticism and spells website. If Internet debauchery wasn't enough, when she goes to purchase the "Book of the Dead," little Lohan doesn't have the necessary funds and instead writes an IOU. Black magic may be harmless fun to you, Lindsay, but stealing is no laughing matter.
Fifth-Degree Assault (with a Volleyball)
After a mystical Chinese fortune cookie switches Lindsay's body with that of her mother in Freaky Friday, Lindsay plays the role of a middle-age woman given a second chance at her teen years with aplomb. But this scene, in which Lindsay gets pummeled in the head by a volleyball so many times that she chooses to fight back, begs this question: Is her mother, played by Jamie Lee Curtis, culpable for assault charges?
Lilo De-Pants Ugly Betty
In the Ugly Betty episode "Granny Panties"—aka Mean Girls 2—Lindsay fit seamlessly into the character of Betty's high-school nemesis, even pantsing Betty in front of the entire cafeteria. Apparently, life imitated art on the set and a feud between America Ferrera and Lindsay cut her guest stint on the show from six episodes to four.
Extorting an Abusive Stepfather
In Georgia Rule, Lindsay's character is so out of control that she gets shipped out to Idaho to live with her grandmother Georgia. It's all very warm and fuzzy until she tells her stepfather she won't release the sex tape of him molesting her if he writes her a letter of apology… and a check for $10 million. And we thought Michael Lohan was bad.
What do you do when your boss is about to fire you? The next logical step, obviously, is to fake a pregnancy. That's what Lindsay's character did in the 2009 straight-to-cable flop Labor Pains. With the aid of a stomach pillow, Lindsay nearly pulls off one of the biggest capers on cable television, until her sister tears the pillow apart in a fit of rage. Minor fraud, sure, but it's a slippery slope.
Sujay Kumar works at The Daily Beast. He's written for MTV Splash Page and The Daily Illini.