Pretty, petite and pert, this Southern belle made her movie debut in 1991's The Man in the Moon at the age of 15. Throughout the '90s, Witherspoon steered clear of typical teen roles and instead turned in complex performances in indie favorites such as Freeway and Election, playing sweet young things who were way tougher than they looked. Cruel Intentions, the adolescent retelling of Dangerous Liaisons, paired her with soon-to-be-husband Ryan Phillippe and made her something of a teen idol. Then her charismatic turn as a Barbie doll with a brain in the 2001 comedy Legally Blonde made her a megastar. Witherspoon continued to land high-profile roles and also began producing her own vehicles, including Legally Blonde 2: Red, White & Blonde. In 2006 she scored a Golden Globe and an Oscar as Johnny Cash's wife in the biopic Walk the Line.