The Jack Raymond Show is a radio program that's been broadcast every day for 49 years from a small, family-operated radio station in Chippewa Falls, Wisconsin. The host of the show is a mysterious figure who has a loyal local following, and still gets fan mail, but he's been dead for over 40 years. This film is the story of Jack Raymond and the eccentric radio station that has unwittingly influenced a generation of local musicians and artists. Featuring Justin Vernon (aka Bon Iver) and narration by Mark Borchardt (American Movie).

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