O'Reilly started her acting career in 2003 in the film, Bill the Intern. She has been in other movies like Dinocroc, Nancy Drew, Just Add Water and Forgetting Sarah Marshall. She also acted in television series like CSI: NY, Unhitched, The Vampire Diaries and Prime Suspect.In 2011, she was a part in the movie The Help based on Kathryn Stockett's bestseller of the same name The Help is a period drama that takes place in Jackson, Mississippi, in the 1960s. The film opened to positive reviews and became a box-office hit with a global gross of $211,608,112. It also took home a number of ensemble awards including National Board of Review Award, Screen Actors Guild Award and Satellite Award. O'Reilly was a co-star with Ashton Kutcher in the 2013 movie Jobs. In 2016, she was in the Roundabout Theatre Company's off-Broadway production of The Robber Bridegroom. A cast recording of O'Reilly portraying Rosamund was released on September 9th on the 9th of September, 2016.
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