YMMV / Ride with the Devil

• Audience-Alienating Premise: The movie portrays an African American fighting on the side of southern guerrillas in the Kansas border skirmishes of the Civil War. Although the character had a historically factual precedent, the idea of a black soldier fighting for the Confederacy, an institution widely associated with white supremacy, was so repugnant that the film was delayed, promotional materials were destroyed, and the release was severely limited (in the actual Confederacy most of the black soldiers were slaves forced into service by their masters though, so it's not as if they were all willing anyway). Even in the film, the character possibly only goes with them because he feels grateful for George freeing him, and suffers from constant racism by the white fighters. This ultimately resulted in the aforementioned extremely limited release of only 60 theaters and it subsequently tanking at the box office.
• Complete Monster: Pitt Mackeson manages to be the Token Evil Teammate of the First Missouri Irregulars with his love for fighting and bloodshed. A young gunslinger who enlisted in the Confederate militia solely for the chance to kill Unionists, Pitt is introduced following his fellow bushwhackers in a plan to attack a pro-Union store, killing a guerilla and amusing himself by repeatedly shooting another in the chest, shouting with excitement afterwards. Pitt then murders the owner while his wife watched everything before torching the store amid the protests of his loyal compatriot. When his group is ambushed by Union soldiers, Pitt stays behind on purpose instead of escaping just to kill more people. Ecstatic upon discovering that they would join in on raiding a town, Pitt gleefully participated in the Lawrence Massacre and killed its first victim. Dissatisfied with how his side was losing the war, Pitt ultimately deserted to indiscriminately plunder and murder with his own gang.
• She Really Can Act: Jewel's role in this movie was generally positively reviewed.