Writer Nancy Meyers handpicked Lohan for the dual-role lead in Disney's big-screen 1998 remake of their 1961 classic, The Parent Trap. Lohan landed some "Best Newcomer" awards as a result and did two TV movies for Disney. She also launched a singing career before starring in an even more successful Disney remake, Freaky Friday (opposite Jamie Lee Curtis).
Lohan's 2004 MTV Award for Best Breakthrough Female was a veritable omen for a year in which she would turn 18, release her first album, grace numerous magazine covers and receive glowing reviews for Confessions of a Teenage Drama Queen and Mean Girls.