- Complete Monster:
- Bill Doolin is a dirty little bandit out to make a big score. Disguising himself and his men as Comanche, he rides into one town, shooting it up and beating the sheriff to near-death in order to frame the peaceful tribe to provoke a war between them and the US military so he can steal a supply of gold. Later freed from jail, Doolin steals a train carrying explosives so he can use them for his scores, heedless of the lives lost, and when Jane faces him, Doolin even tries to kill her beloved horse just to hurt her more before he kills her.
- Mr. Filbert, from "Troubled Waters", is an arrogant, racist bureaucrat in the pocket of his greedy higher-ups. He proves himself far worse than most disposable bureaucrats by muscling onto Apache territory while trying to use outdated legal tactics to force them off. When intimidation fails, Filbert forces Sheriff O'Rourke to push them off and shoot any who resist, eventually revealing his plans to murder their leader to spur them into war and massacre them all to the last, even trying to burn Jane and O'Rourke to death for getting in his way.
- What Do You Mean, "It's for Kids"?: It's not particularly surprising one of the major suspected reasons Jane was pulled from WB was because of its controversial content, which the show was rife with — for as few times people were actually shot with the guns themselves, the show still had tons of brutal Family-Unfriendly Violence and episodes openly addressing mature themes like racism and sexism as well as rather explicitly detailed of some of the brutality of the Civil War and its fallout (such as a character whose brother is guilty over having to failed to prevent Lincoln's assassination, and a xenophobic government agent planning to have the Comanche people massacred). Alongside that, the show tiptoes into some odd sexual material as well, with a brothel and its prostitutes only obscured by the fact nobody is calling them such out loud, and the story Jane tells to young Eleanor Roosevelt about the first time she killed someone, who was blatantly attempting to rape her.
YMMV / The Legend of Calamity Jane