The "black bandana-optional," outdoor screening is slated to take place Thursday at the Kearney farmstead where James was born, raised, and, eventually buried.
Jesse James' great-granddaughter, Betty Barr, is expected to attend the fete, which will feature re-enactments and a musical performance by a cowboy band.
Pitt is also a Missouri native.
The tourism board said in a statement it is presenting the event to "recognize the celebrity of two of the Show-Me state's most famous sons -- Brad Pitt and Jesse James -- and, more importantly, to remind people that they can see and experience the authentic Missouri sites where Jesse James rode, robbed, lived and died."
Starting Sept. 21, visitors can see Clay County Historic Sites' new film about James's life as part of its tour of the Jesse James Farm & Museum.