Having been banished from shooting in New Hampshire, director Walt Price (WILLIAM H. MACY) and his Hollywood film crew, including cinematographer Uberto Pazzi (VINNE GUSTAFERO) and first assistant director Tommy Max (JIM GRANGIONE), arrive in the small town of Waterford, Vermont short of both money and time. With only a few days before his cast arrives, Walt needs a locale to pass for the 19th century setting of his film, "The Old Mill."
Unfortunately, and despite what the brochures say, the town hasn't had an old mill since it and other structures mysteriously burned down in the 1960s. Unfazed and ever resourceful, Walt simply tells novice screenwriter Joe White (PHILIP SEYMOUR HOFFMAN) to write the old mill out the movie, but the scribe can't even do that since he can't find a manual typewriter.
Fortunately for him, local bookstore proprietor and community theater director Ann Black (REBECCA PIDGEON) has several. Kindred spirits, she and Joe immediately hit it off, despite her being engaged to ambitious politician, Doug MacKenzie (CLARK GREGG), who's determined to squeeze as much money out of the production for the town as possible.
While Waterford's mayor, George Bailey (CHARLES DURNING) and his wife Sherry (PATTI LuPONE) prepare for a huge dinner at their home, stars Bob Barrenger (ALEC BALDWIN) and Claire Wellesley (SARAH JESSICA PARKER) arrive in town, each bringing their own set of complications. While Barrenger's penchant for under-aged girls keeps everyone on their toes - especially after he meets local waitress Carla Taylor (JULIA STILES) - the bigger concern is Claire's sudden decision not to do a topless scene as previously agreed upon in her contract.
As such, Walt calls in producer Marty Rossen (DAVID PAYMER) who's known for his strong-arm tactics. As he gets after Claire to do the scene, Joe tries to keep up with the many story changes and Barrenger gets into a car accident with a young woman that has to be covered up, Walt does what he can to keep the film on schedule and get his shots no matter what that might take.