Movie: Twilight (1999)
Thanks to Legally Blonde and her numerous rom-coms, it's hard to imagine Witherspoon out of her J. Crew wardrobe and her pink powersuits. But actually, if you look at her resume before 1999, when she cultivated her “America’s Sweetheart” image, Witherspoon’s take on a number of risque roles. Case in point: lesser known thriller Twilight, in which Witherspoon’s character, Mel Ames, strips down with her ex-con boyfriend.