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In this comedy, Lindsay Lohan plays Ashley, a young professional just out of college. She also happens to be the luckiest woman in the world, who has lived a super-charmed life and has always taken her good luck for granted. When she kisses a handsome stranger (played by Chris Pine) at a costume party, Ashley accidentally swaps her good fortune for his horribly bad luck, and her charmed life turns into a living hell.
The movie is a celebrity version of Garrison Keillor's radio show. It adds a slight story of the radio show ending as a new owner (Tommy Lee Jones) has bought the Fitzgerald theater that the show broadcasts from and is going to tear it down. Another fantasy element is thrown in as an angel (Virginia Madsen) stalks the theater to take one of the performers. Keillor plays the lead character, coincidentally called GK. Lily Tomlin and Meryl Streep play the singing Johnson Sisters, with Lindsay Lohan as a suicide-obsessed daughter of Streep. Woody Harrelson and John C. Reilly are hilarious as the slightly off-color singing cowboy duo, Dusty & Lefty. Kevin Kline is a security guard who tells the story. Maya Rudolph also appears as a pregnant stage coordinator. Contains some mild sexually-oriented jokes.