Lindsay Lohan

At the age of 14, Lohan played Bette Midler's daughter in the pilot episode of the short-lived series, Bette, but resigned her role when the production moved from New York to Los Angeles. She also starred in two Disney television movies: Life-Size opposite Tyra Banks in 2000, and Get a Clue in 2002.
• 2003–04: Freaky Friday, Mean Girls and Speak
Lohan starred as Anna Coleman alongside Jamie Lee Curtis in the 2003 family comedy Freaky Friday. At Lohan's own initiative, her character was rewritten and changed from a Goth style to be more relatable. Critic Roger Ebert wrote that Lohan "has that Jodie Foster sort of seriousness and intent focus beneath her teenage persona." Freaky Friday earned Lohan the award for Breakthrough Performance at the 2004 MTV Movie Awards and, as of 2010, it remains her most commercially successful film, earning $160 million worldwide as well as an 88 percent approval rating on Rotten Tomatoes.
Aiming to become a triple threat — actor, singer and dancer, similar to Ann-Margret and Marilyn Monroe — Lohan began showcasing her singing through her acting. For the Freaky Friday soundtrack, she sang the closing theme, "Ultimate," as well as recording four songs for the Confessions of a Teenage Drama Queen soundtrack. Producer Emilio Estefan, Jr. signed Lohan to a five-album production deal in 2002. Two years later, Lohan signed a recording contract with Casablanca Records, headed by Tommy Mottola.