Oscar Stars' Most Embarrassing Roles

Reese Witherspoon, How Do You Know (2010)

After making a splash as the lead in campy 2001 hit Legally Blonde, it seemed as though Reese Witherspoon was set to become typecast as a rom-com staple. But when the actress landed the role as Johnny Cash's wife June Carter in 2005's Walk the Line, she transitioned into Oscar territory, taking home the Best Actress statue that year. Flash-forward five years, however, and Witherspoon made a movie misstep with lackluster How Do You Know.

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