Oscar Stars' Most Embarrassing Roles

Jessica Chastain, Blackbeard (2006)

Hollywood's current "It" girl got her start in Hollywood doing guest appearances on Veronica Mars and ER. But in 2006, the fiery-haired actress landed one of the leads in the TV movie Blackbeard -- clearly a step in the right direction, because the 35-year-old actress is now a frontrunner for a Best Actress win with her role as a hot-headed agent in Kathryn Bigelow's Zero Dark Thirty.

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