She did more television work as she grew up, including stints on soap operas like Another World and The Guiding Light, as well as roles in The Bette Show and Get a Clue, a Disney Channel movie. Lohan's Disney connection, which included starring as the twins in a remake of The Parent Trap, continued into her teens and helped her expand her career into music: along with co-starring with Jamie Lee Curtis in 2003's Freaky Friday, she also performed the movie's theme song, "Ultimate."

The following year, Lohan starred in Confessions of a Teenage Drama Queen and contributed two songs to its soundtrack. Buoyed by these successes as well as her starring role in Mean Girls, Lohan hosted the 2004 MTV Movie Awards and won an award for Female Breakout Star. She also signed to Tommy Mottola's Casablanca Records, releasing her debut album, Speak, in December of 2004. The next year saw celebrity start to catch up with Lohan. While she continued her relationship with Disney, filming a remake of Herbie: Fully Loaded, Internet and tabloid rumors spread about everything from her health and love life (she's dating Wilmer, she isn't dating Wilmer....) to her late-night party habits and diva behavior. It didn't help that Speak was less than a success.

By the end of 2005 Lohan's persona as the wild and damaged teen siren -- whatever its ratio of truth to fiction -- had outshone her accomplishments as an actress and a singer. And it was into this caustic tabloid climate that she released her second album, A Little More Personal (Raw). Though the album was critically panned, it was certified gold early in 2006. Later that year, Lohan was switched from Casablanca to Motown Records by Universal Music Group. Though she focused more on her film career in 2006 and 2007 and continued to have a swirl of tabloid attention and media controversy around her -- including her arrest on May 26, 2007, for suspicion of driving under the influence and a subsequent stay at Malibu, CA's Promises Treatment Center -- Lohan planned work on a third album in the second half of 2007. ~ Heather Phares