When 15-year-old Lindsay Lohan starred as a punk-pop singer in the 2003 remake of the Disney movie Freaky Friday, she was only one step away from actually becoming a teen pop star. Positive reviews of her performance of the film's closing song, "Ultimate," led to a deal with Casablanca Records. Lohan's debut album, Speak, reached Number Four in 2004 and produced the Top 40 Mainstream hits "Rumors" (Number 23, 2004) and "Over" (Number 39, 2005). In subsequent years, Lohan became known more for her hard partying and run-ins with the law than for her acting or singing.
She was born Lindsay Dee Lohan in the Bronx, New York, on July 2nd, 1986, and raised in the Long Island town of Cold Spring Harbor. Her parents — Donata "Dina" Lohan and troubled Wall Street trader Michael Douglas Lohan, Sr. — signed their eldest daughter to the Ford modeling agency when she was three years old. She eventually appeared in print ads for Toys R Us and also modeled for Calvin Klein Kids along with her siblings. As a child model, she appeared in magazines including Vogue and Elle, and later acted in commercials for companies including Duncan Hines and Jell-O. Her TV appearances led to her role, at 10, as Alexandra "Alli" Fowler on the soap opera Another World. When she was 12, Lohan landed the duel role of twin sisters in the successful and well-received 1998 comedy The Parent Trap, which earned $92 million in worldwide box office sales. Disney signed the young actress to a three-film contract, and she starred two TV movies, Life-Size (2000) and Get a Clue (2002). After landing a brief role as Bette Midler's daughter in the unsuccessful sitcom Bette, Lohan's family relocated to Los Angeles, where in 2001 she hosted an ABC special to commemorate Walt Disney's 100th birthday. In 2003, she appeared as Jamie Lee Curtis' punk-rock daughter in Disney's Freaky Friday, which earned $160 million in worldwide box office sales.
The success of Freaky Friday raised Lohan's profile significantly, and she appeared in a string of subsequent films including Confessions of a Teenage Drama Queen and Mean Girls in 2004, and Herbie: Fully Loaded and Just My Luck in 2005. Mean Girls earned two MTV Movie Awards, for Best Female Performance and Best On Screen Team. She followed her debut album with A Little More Personal (Raw), which reached Number 20 in 2005 and produced the single "Confessions of a Broken Heart (Daughter to Father)." The song was a musical open letter to her father, who had experienced legal problems throughout Lohan's childhood. Lohan self-produced the video, which also featured her sister Ali and showed a family's domestic problems being played out in front of an audience outside the windows of their home. Lohan's personal and professional lives had begun to collide in 2005.
That year, her father, who in the Nineties had been investigated for insider trading and served prison time for criminal contempt of court, was sentenced to prison again on assault and DUI charges. In December 2005, he and Dina signed a separation agreement. The divorce became final in 2007. By then, Lohan's own legal problems were making headlines. Though she had landed supporting roles in big films such as Bobby and A Prairie Home Companion, in 2006, and starred in another 2006 film, Chapter 27, her inconsistent work habits, weight loss and frequent accidents were the source of much speculation in the Hollywood gossip columns. In July 2006, filming of the movie Georgia Rule, in which she appeared alongside Jane Fonda, was delayed when Lohan entered a hospital for dehydration. The film's producer suggested in a public letter that the actress' health problems might be due to her partying. In the midst of all that, Lohan hosted Saturday Night Live twice, once on May 21st, 2005 and again on April 15th, 2006.
Lohan's problems escalated in 2007. In January, she checked herself into a West Hollywood rehab clinic. In May, she crashed her Mercedes-Benz and was charged with DUI. She returned to rehab, this time going to Promises Treatment Center in Malibu for a 45-day stay. In July, shortly after a court appearance in which she was let go on her own recognizance, she was arrested again, this time on charges of DUI and driving with a suspended license as well as possession of cocaine and transportation of a narcotic. Shortly thereafter she checked into another rehab, Cirque Lodge, in Sundance, Utah, and in August was sentenced to one day in jail and 10 days community service for the DUIs. She also was ordered to complete an alcohol education program. Meanwhile, she also starred in two successful but critically panned movies that year: the comedy drama Georgia Rule and thriller I Know Who Killed Me.
As of 2008, two Lohan movies — Dare to Love Me and Poor Things — were scheduled for release. She also announced she was working on a third album, tentatively titled Spirit in the Dark, featuring production by Pharrell, Stargate, Bloodshy & Avant and Akon. The album's first single, "Playground," featuring Pharrell, is slated for September release; the album is due in November. (Lohan also appeared in the video for NERD's "Everyone Nose," a song about recreational drug use at parties). In mid-2008, gossip columnists tracking Lohan's personal life began reporting that the singer-actress, who was previously linked to Aaron Carter, actor Wilmer Valderrama, restauranteur Harry Morton and fellow rehab attendee Riley Giles, was seeing her friend, the DJ Samantha Ronson.