Lindsay Lohan was already an experienced performer when she made her feature debut in the 1998 remake of The Parent Trap.
Born in New York City, Lohan began modeling at age three. After appearing in numerous TV commercials, Lohan moved to series TV with a role on the soap operaAnother World from 1996 to 1997. Cast as The Parent Trap's scheming twin sisters after a six month search for just the right girl, Lohan succeeded in filling Hayley Mills' shoes, winning over audiences with her pert charm as both the Californian Hallie and the British-raised Annie. She subsequently starred in the Disney TV film Life-Size (2000). Subsequently cast in actress Bette Midler's short-lived sitcom Bette, Lohan took a turn as a teenage gossip columnist (Get a Clue) before turning up in yet another remake of a Disney classic, Freaky Friday (2003). Stepping into the shoes formerly filled by Jodie Foster, Lohan and co-star Jamie Lee Curtis brought a winning, new chemistry to the film that made it a sleeper summer hit.
Lohan kicked off 2004 with her first big starring vehicle, the comedy Confessions of a Teenage Drama Queen. Met with mixed reviews and modest box-office receipts, the film didn't cross over from the teen audience the way Friday did. Only a mere two months later, Lohan proved she could carry a film. The Tina Fey-penned Mean Girls debuted at number one, recouping its budget and then some in its first week of release. The spotlight on the then-16-year-old Lohan changed almost overnight, as she quickly became a tabloid fixture: speculation on her body, her nightclubbing, her string of high-profile boyfriends, her incarcerated father, and her feuds with a variety of other young female celebrities became inescapable. Perhaps predictably, 2004 also saw Lohan branch out into the world of pop music with the album Speak; the supposedly confessional -- and similarly undistinguished -- A Little More Personal followed in 2005.
All of the hullabaloo seemed to have little effect on her work, as she starred in Herbie: Fully Loaded for Disney -- suffering a bout of "exhaustion" on set -- before graduating to more adult fare with Robert Altman's A Prairie Home Companion. Playing a morose poetess, the young actress ably held her own against Meryl Streep and Lily Tomlin when the film opened in 2006; around that time, her first shot at a "grown-up" romantic comedy, Just My Luck, opened to little notice from the public or critics.
Undaunted, Lohan set to work on another grande-dame comedy, Georgia Rule, in which she played a wayward, risk-taking teenage girl who is hauled off to live with her stern grandmother (Jane Fonda) for the summer. Perhaps fittingly, Lohan's own tardy behavior on the Georgia Rule set prompted a very public memo from the film's backers, who claimed her late-night partying was endangering the shoot; a short stay in rehab followed in early 2007. For all the publicity generated by Lohan's wild-child routine, Georgia Rule tanked when it opened in May of that year, although many critics preferred Lohan's performance over those of her histrionic co-stars Jane Fonda and Felicity Huffman. The actress' R-rated summer blitz continued with the thriller I Know Who Killed Me, just as her work in the widely panned Mark David Chapman biopic Chapter 27 made the festival rounds. This trifecta of flops was complemented by an increasingly erratic public image, as she found herself involved in two DUI arrests within two months' time that same summer. Both prompted stays in rehab, as well as mammoth media attention.