Most Infamous Moment: After a night out in Hollywood in 2007, Lohan drove drunk into a tree, fled the scene, and the cops found cocaine in her car.

When we first met Lindsay Lohan, she was the adorable freckle-faced teen starring in such films as The Parent Trap, Freaky Friday and Mean Girls. However, over the course of the last decade, Lindsay’s gradually started spending more time in Los Angeles courtrooms than on Hollywood backlots, two of the reasons being an apparent jewelry theft and her multiple car accidents. Whether she’s on TMZ wearing a court-ordered ankle bracelet or in the pages of Playboy wearing absolutely nothing, controversy seems to follow Ms. Lohan wherever she goes.