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Alex (Luke Wilson) is an author whose writer's block and gambling debts have landed him in a jam. In order get loan sharks off his back, he must finish his novel in 30 days or wind up dead. To help him complete his manuscript he hires stenographer Emma (Kate Hudson). As Alex begins to dictate his tale of a romantic love triangle to the charming yet somewhat opinionated stenographer, Emma challenges his ideas at every turn. Her unsolicited yet intriguing input begins to inadvertently influence Alex and his story and soon real life begins to imitate art.
Set somewhere, sometime, in an unnamed country, torn by civil war with unclear battle lines or ideology, "Masked and Anonymous" tells the story of a "benefit concert." Impressario Uncle Sweetheart (John Goodman) is scheming to find a headliner for this event whose purpose is unclear and whose charity is its promoter's pockets. Nina Veronica (Jessica Lange) is the veteran TV producer whose job it is to make the concert the international spectacle which it can never be. And when Sweetheart manages to get the iconic cult star Jack Fate (Bob Dylan) released from prison, the stage is set for tumult. Jeff Bridges as the cynical investigative reporter, Penélope Cruz as his girlfriend, Luke Wilson as the devoted acolyte, and a sundry cast of supporting characters give this imaginative allegory its energy and spirit.