Bloody Kansas

The Outlaw Josey Wales (1976)
For vengeance joins "Bloody Bill" Anderson's gang, a pro-southern gang of "outlaws" or better said "war criminals"
Quantrill’s Raiders (1958)
Psychopath leading outlaws with a pro-southern slant
Kansas Raiders (1950)
Jesse James joins Quantrill's Raiders
Dark Command (1940)
Civil War Kansas; Quantrill's Raiders
Ride with the Devil (1999)
The war in bloody Kansas and Missouri
The Jayhawkers! (1959)
A government agent infiltrates the vigilante group the Jayhawkers (bushwhackers were pro-South and Jayhawkers were pro-union, non-military guerilla raiders)
Seven Angry Men (1955)
John Brown (Raymond Massey)
Santa Fe Trail (1940)
On trail of John Brown; 1856 Pottawatomie Creek massacre; 1859 Harper's Ferry