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In June 2008, she joined the cast of the Polish brothers comedy Stay Cool. Hilary Duff co-starred alongside Winona Ryder, Mark Polish, Sean Astin, Chevy Chase, and Jon Cryer. In the film, Hilary Duff portrayed the character of Shasta O'Neil, described as a s*xy high school senior and the film is scheduled for release in 2009.

In November 2008, her 2nd greatest hits album, Best of Hilary Duff was released and the album's 1st single "Reach Out" which samples Depeche Mode's "Personal Jesus" was released in the previous month, the song became her 3rd number one dance hit. Hilary Duff thereafter announced that Hilary Duff would be leaving her record label Hollywood Records after 6 years of service. Hilary Duff later announced to MTV that she would begin work on her new album in December 2008.

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