Lindsay Lohan

There was a time when Lindsay Lohan was Hollywood’s next great hope. Don’t laugh! It’s easy to forget, in the TMZ era, that the onetime Parent Trap star broke out in the early part of the decade with two huge teen films. Freaky Friday presented Lohan as a talent to watch, as she mimicked her onscreen mom Jamie Lee Curtis’s mannerisms impeccably. But it was the high-school black comedy Mean Girls, written by Tina Fey, that made Lohan—onscreen, the unpopular girl who becomes queen bee—a star. Suddenly, she was everywhere. From early on, it seemed the girl from Long Island had her sights set on bigger things: she recorded two albums, hosted three above-average Saturday Night Live episodes and the MTV Movie Awards, and signed on for a Robert Altman film. Then the wheels came off the bus, with rehab, an arrest, and embarrassing confessions. The last major career move Lohan made was imitating Marilyn Monroe’s last photo shoot for New York magazine. These days, it’s hard to imagine her pulling herself together long enough for a photo shoot, let alone a movie. Rather than the romantic-comedy superstar she was supposed to be, Lohan debuted this decade as one of our best cautionary tales.