While Witherspoon is most known for her role as Elle Woods in "Legally Blonde," the actress spent the early half of the decade cementing her status as a rising star. She starred in 1999's "Cruel Intentions" with fellow '90s stars Sarah Michelle Gellar, Selma Blair, and first husband Ryan Phillipe.

She became a leading lady in romantic comedies like "Sweet Home Alabama," and took home a Best Actress Oscar in 2006 for her role in "Walk the Line." Most recently, she made the crossover to the small screen in HBO's "Big Little Lies." The Golden Globe and Emmy winning series' second season is slated to premiere in June 2019.